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N,N-Dimethyltryptamine

February 16, 2024

"DMT" redirects here. For other uses, see DMT (disambiguation).

N,N-Dimethyltryptamine (DMT or N,N-DMT) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine.[4] DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.[5]

N,N-Dimethyltryptamine
Clinical data
Routes of
administration		Oral (with an MAOI), vaporized, insufflated, rectal, IM, IV
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life9-12 minutes
Identifiers
  • 2-(1H-Indol-3-yl)-N,N-dimethylethanamine
CAS Number
  • 61-50-7 Y
PubChem CID
  • 6089
IUPHAR/BPS
  • 141
DrugBank
  • DB01488 Y
ChemSpider
  • 5864 Y
UNII
  • WUB601BHAA
KEGG
  • C08302 Y
ChEBI
  • CHEBI:28969 Y
ChEMBL
  • ChEMBL12420 Y
CompTox Dashboard (EPA)
  • DTXSID60110053
ECHA InfoCard100.000.463
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.099 g/cm3
Melting point40 °C (104 °F)
Boiling point160 °C (320 °F) at 0.6 Torr (80 Pa)[2]
also reported as
80–135 °C (176–275 °F) at 0.03 Torr (4.0 Pa)[3]
  • CN(CCC1=CNC2=C1C=CC=C2)C
  • InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3 Y
  • Key:DMULVCHRPCFFGV-UHFFFAOYSA-N Y
  (verify)

DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms.[6] DMT can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last a short period of time: about five to 15 minutes. Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (MAOI), such as the ayahuasca brew of many native Amazonian tribes.[7] DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms.[8]

DMT is a functional analog and structural analog of other psychedelic tryptamines such as O-acetylpsilocin (4-AcO-DMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), O-methylbufotenin (5-MeO-DMT), and bufotenin (5-HO-DMT). Parts of the structure of DMT occur within some important biomolecules like serotonin and melatonin, making them structural analogs of DMT.

Human consumption edit

DMT is produced in many species of plants often in conjunction with its close chemical relatives 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and bufotenin (5-OH-DMT).[9] DMT-containing plants are commonly used in indigenous Amazonian shamanic practices. It is usually one of the main active constituents of the drink ayahuasca;[10][5] however, ayahuasca is sometimes brewed with plants that do not produce DMT. It occurs as the primary psychoactive alkaloid in several plants including Mimosa tenuiflora, Diplopterys cabrerana, and Psychotria viridis. DMT is found as a minor alkaloid in snuff made from Virola bark resin in which 5-MeO-DMT is the main active alkaloid.[9] DMT is also found as a minor alkaloid in bark, pods, and beans of Anadenanthera peregrina and Anadenanthera colubrina used to make Yopo and Vilca snuff, in which bufotenin is the main active alkaloid.[9][11] Psilocin and psilocybin, the main psychoactive compounds in psilocybin mushrooms, are structurally similar to DMT.

The psychotropic effects of DMT were first studied scientifically by the Hungarian chemist and psychologist Stephen Szára, who performed research with volunteers in the mid-1950s. Szára, who later worked for the United States National Institutes of Health, had turned his attention to DMT after his order for LSD from the Swiss company Sandoz Laboratories was rejected on the grounds that the powerful psychotropic could be dangerous in the hands of a communist country.[12]

DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor such as a reversible inhibitor of monoamine oxidase A (RIMA), for example, harmaline.[5] Without a MAOI, the body quickly metabolizes orally administered DMT, and it therefore has no hallucinogenic effect unless the dose exceeds the body's monoamine oxidase's metabolic capacity. Other means of consumption such as vaporizing, injecting, or insufflating the drug can produce powerful hallucinations for a short time (usually less than half an hour), as the DMT reaches the brain before it can be metabolized by the body's natural monoamine oxidase. Taking an MAOI prior to vaporizing or injecting DMT prolongs and enhances the effects.[8]

Clinical use research edit

Dimethyltryptamine (DMT), an endogenous ligand of sigma-1 receptors (Sig-1Rs), acts against systemic hypoxia. Research demonstrates DMT reduces the number of apoptotic and ferroptotic cells in mammalian forebrain and supports astrocyte survival in an ischemic environment. According to these data, DMT may be considered as adjuvant pharmacological therapy in the management of acute cerebral ischemia.[13]

DMT is studied as a potential treatment for Parkinson’s disease in a Phase 1/2 clinical trial.[14]

SPL026 (DMT fumarate) is currently undergoing phase II clinical trials investigating its use alongside supportive psychotherapy as a potential treatment for major depressive disorder.[15] Additionally, a safety study is underway to investigate the effects of combining SSRIs with SPL026.[16]

Neuropharmacology edit

Recently, researchers discovered that N,N-dimethyltryptamine is a potent psychoplastogen, a compound capable of promoting rapid and sustained neuroplasticity that may have wide-ranging therapeutic benefit.[17]

Quantities of dimethyltryptamine and O-methylbufotenin were found present in the cerebrospinal fluid of humans in a psychiatric study.[18]

Effects edit

See also: Ayahuasca § Effects

Subjective psychedelic experiences edit

Subjective experiences of DMT includes profound time-dilatory, visual, auditory, tactile, and proprioceptive distortions and hallucinations, and other experiences that, by most firsthand accounts, defy verbal or visual description.[19] Examples include perceiving hyperbolic geometry or seeing Escher-like impossible objects.[20]

Several scientific experimental studies have tried to measure subjective experiences of altered states of consciousness induced by drugs under highly controlled and safe conditions.

Rick Strassman and his colleagues conducted a five-year-long DMT study at the University of New Mexico in the 1990s.[21] The results provided insight about the quality of subjective psychedelic experiences. In this study participants received the DMT dosage via intravenous injection and the findings suggested that different psychedelic experiences can occur, depending on the level of dosage. Lower doses (0.01 and 0.05 mg/kg) produced some aesthetic and emotional responses, but not hallucinogenic experiences (e.g., 0.05 mg/kg had mild mood elevating and calming properties).[21] In contrast, responses produced by higher doses (0.2 and 0.4 mg/kg) researchers labeled as "hallucinogenic" that elicited "intensely colored, rapidly moving display of visual images, formed, abstract or both". Comparing to other sensory modalities the most affected was the visual. Participants reported visual hallucinations, fewer auditory hallucinations and specific physical sensations progressing to a sense of bodily dissociation, as well as to experiences of euphoria, calm, fear, and anxiety.[21] These dose-dependent effects match well with anonymously posted "trip reports" online, where users report "breakthroughs"[clarification needed] above certain doses.[22][23][24]

Strassman also stressed the importance of the context where the drug has been taken. He claimed that DMT has no beneficial effects of itself, rather the context when and where people take it plays an important role.[12][21]

It appears that DMT can induce a state or feeling where the person believes to "communicate with other intelligent lifeforms" (see "machine elves"). High doses of DMT produce a state that involves a sense of "another intelligence" that people sometimes describe as "super-intelligent", but "emotionally detached".[21]

A 1995 study by Adolf Dittrich and Daniel Lamparter found that the DMT-induced altered state of consciousness (ASC) is strongly influenced by habitual rather than situative factors. In the study, researchers used three dimensions of the APZ questionnaire to examine ASC. The first dimension, oceanic boundlessness (OB), refers to dissolution of ego boundaries and is mostly associated with positive emotions.[25] The second dimension, anxious ego-dissolution (AED), represents a disordering of thoughts and decreases in autonomy and self-control. Last, visionary restructuralization (VR) refers to auditory/visual illusions and hallucinations.[26] Results showed strong effects within the first and third dimensions for all conditions, especially with DMT, and suggested strong intrastability of elicited reactions independently of the condition for the OB and VR scales.[25]

Reported encounters with external entities edit

Entities perceived during DMT inebriation have been represented in diverse forms of psychedelic art. The term machine elf was coined by ethnobotanist Terence McKenna for the entities he encountered in DMT "hyperspace", also using terms like fractal elves, or self-transforming machine elves.[27][28] McKenna first encountered the "machine elves" after smoking DMT in Berkeley in 1965. His subsequent speculations regarding the hyperdimensional space in which they were encountered have inspired a great many artists and musicians, and the meaning of DMT entities has been a subject of considerable debate among participants in a networked cultural underground, enthused by McKenna's effusive accounts of DMT hyperspace.[29] Cliff Pickover has also written about the "machine elf" experience, in the book Sex, Drugs, Einstein, & Elves.[7] Strassman noted similarities between self-reports of his DMT study participants' encounters with these "entities", and mythological descriptions of figures such as Ḥayyot haq-Qodesh in ancient religions, including both angels and demons.[30] Strassman also argues for a similarity in his study participants' descriptions of mechanized wheels, gears and machinery in these encounters, with those described in visions of encounters with the Living Creatures and Ophanim of the Hebrew Bible, noting they may stem from a common neuropsychopharmacological experience.[30]

Strassman argues that the more positive of the "external entities" encountered in DMT experiences should be understood as analogous to certain forms of angels:

The medieval Jewish philosophers whom I rely upon for understanding the Hebrew Bible text and its concept of prophecy portray angels as God's intermediaries. That is, they perform a certain function for God. Within the context of my DMT research, I believe that the beings that volunteers see could be conceived of as angelic – that is, previously invisible, incorporeal spiritual forces that are engarbed or enclothed in a particular form – determined by the psychological and spiritual development of the volunteers – bringing a particular message or experience to that volunteer.[31]

Strassman's experimental participants also note that some other entities can subjectively resemble creatures more like insects and aliens.[32] As a result, Strassman writes these experiences among his experimental participants "also left me feeling confused and concerned about where the spirit molecule was leading us. It was at this point that I began to wonder if I was getting in over my head with this research."[33]

Hallucinations of strange creatures had been reported by Stephen Szara in a 1958 study in psychotic patients, in which he described how one of his subjects under the influence of DMT had experienced "strange creatures, dwarves or something" at the beginning of a DMT trip.[34][35]

Other researchers of the entities seemingly encountered by DMT users describe them as "entities" or "beings" in humanoid as well as animal form, with descriptions of "little people" being common (non-human gnomes, elves, imps, etc.).[36][37] Strassman and others have speculated that this form of hallucination may be the cause of alien abduction and extraterrestrial encounter experiences, which may occur through endogenously-occurring DMT.[38][39]

Likening them to descriptions of rattling and chattering auditory phenomena described in encounters with the Hayyoth in the Book of Ezekiel, Rick Strassman notes that participants in his studies, when reporting encounters with the alleged entities, have also described loud auditory hallucinations, such as one subject reporting typically "the elves laughing or talking at high volume, chattering, twittering".[30]

Near-death experience edit

A 2018 study found significant relationships between a DMT experience and a near-death experience.[40] A 2019 large-scale study pointed that ketamine, Salvia divinorum, and DMT (and other classical psychedelic substances) may be linked to near-death experiences due to the semantic similarity of reports associated with the use of psychoactive compounds and NDE narratives, but the study concluded that with the current data it is neither possible to corroborate nor refute the hypothesis that the release of an endogenous ketamine-like neuroprotective agent underlies NDE phenomenology.[41]

Physiological response edit

According to a dose-response study in human subjects, dimethyltryptamine administered intravenously slightly elevated blood pressure, heart rate, pupil diameter, and rectal temperature, in addition to elevating blood concentrations of beta-endorphin, corticotropin, cortisol, and prolactin; growth hormone blood levels rise equally in response to all doses of DMT, and melatonin levels were unaffected."[21]

Conjecture regarding endogenous effects edit

In the 1950s, the endogenous production of psychoactive agents was considered to be a potential explanation for the hallucinatory symptoms of some psychiatric diseases; this is known as the transmethylation hypothesis.[42] Several speculative and yet untested hypotheses suggest that endogenous DMT is produced in the human brain and is involved in certain psychological and neurological states.[43] DMT is naturally occurring in small amounts in rat brain, human cerebrospinal fluid, and other tissues of humans and other mammals.[44][45][46][47] Further, mRNA for the enzyme necessary for the production of DMT, INMT, are expressed in the human cerebral cortex, choroid plexus, and pineal gland, suggesting an endogenous role in the human brain.[48] In 2011, Nicholas V. Cozzi, of the University of Wisconsin School of Medicine and Public Health, concluded that INMT, an enzyme that is associated with the biosynthesis of DMT and endogenous hallucinogens, is present in the primate (rhesus macaque) pineal gland, retinal ganglion neurons, and spinal cord.[49] Neurobiologist Andrew Gallimore (2013) suggested that while DMT might not have a modern neural function, it may have been an ancestral neuromodulator once secreted in psychedelic concentrations during REM sleep, a function now lost.[36]

Adverse effects edit

Mental disorders edit

DMT may trigger psychological reactions, known colloquially as a "bad trip", such as intense fear, paranoia, anxiety, panic attacks, and substance-induced psychosis, particularly in predisposed individuals.[50][51]

In fact these experiences are an essential part of the process for the subject whereby they face an overcome these fears and as a result gain significant psychological benefits like enhanced confidence, self worth and self reliance. Research now supports the theory that the more of this type of experience that occurs during a trip the more benefit that the subject enjoys post trip. This is why set, setting and post trip integration are all of paramount importance. Its also important to bear in mind the vad trip experience is short lived and transitory and the subject is never in any real danger. Such experiences are often referred to as ego death.

Addiction and dependence liability edit

DMT, like other serotonergic psychedelics, is considered to be non-addictive with low abuse potential.[19] A study examining substance use disorder for DSM-IV reported that almost no hallucinogens produced dependence, unlike psychoactive drugs of other classes such as stimulants and depressants.[50][52] At present, there have been no studies that report drug withdrawal syndrome with termination of DMT, and dependence potential of DMT and the risk of sustained psychological disturbance may be minimal when used infrequently; however, the physiological dependence potential of DMT and ayahuasca has not yet been documented convincingly.[53]

Tolerance edit

Unlike other classical psychedelics, studies report that DMT did not exhibit tolerance upon repeated administration of twice a day sessions, separated by 5 hours, for 5 consecutive days; field reports suggests a refractory period of only 15 to 30 minutes, while the plasma levels of DMT was nearly undetectable 30 minutes after intravenous administration.[54] Another study of four closely spaced DMT infusion sessions with 30 minute intervals also suggests no tolerance buildup to the psychological effects of the compound, while heart rate responses and neuroendocrine effects were diminished with repeated administration.[54] A fully hallucinogenic dose of DMT did not demonstrate cross-tolerance to human subjects who are highly tolerant to LSD;[55] researches suggest that DMT exhibits unique pharmacological properties compared to other classical psychedelics.[54]

Long-term use edit

There have been no serious adverse effects reported on long-term use of DMT, apart from acute cardiovascular events.[51] Repeated and one-time administration of DMT produces marked changes in the cardiovascular system,[51] with an increase in systolic and diastolic blood pressure; although the changes were not statistically significant, a robust trend towards significance was observed for systolic blood pressure at high doses.[56]

Drug-interactions edit

DMT is inactive when ingested orally due to metabolism by MAO, and DMT-containing drinks such as ayahuasca have been found to contain MAOIs, in particular, harmine and harmaline.[56] Life-threatening lethalities such as serotonin syndrome (SS) may occur when MAOIs are combined with certain serotonergic medications such as SSRI antidepressants.[57][50] Serotonin syndrome has also been reported with tricyclic antidepressants, opiates, analgesic, and antimigraine drugs; it is advised to exercise caution when an individual had used dextromethorphan (DXM), MDMA, ginseng, or St. John’s wort recently.[50]

Chronic use of SSRIs, TCAs, and MAOIs diminish subjective effects of psychedelics due to presumed SSRI-induced 5-HT2A receptors downregulation and MAOI-induced 5-HT2A receptor desensitization.[58]: 145  The interaction between psychedelics and antipsychotics and anticonvulsant are not well documented, however reports reveal that co-use of psychedelics with mood stabilizers such as lithium may provoke seizure and dissociative effects in individuals with bipolar disorder.[59][58]: 146 

Routes of administration edit

Inhalation edit

 
Free base DMT extracted from Mimosa hostilis root bark (left); vape cartridge made with freebase DMT extract (right)

A standard dose for vaporized DMT is 20–60 milligrams, depending highly on the efficiency of vaporization as well as body weight and personal variation.[60][medical citation needed] In general, this is inhaled in a few successive breaths, but lower doses can be used if the user can inhale it in fewer breaths (ideally one). The effects last for a short period of time, usually 5 to 15 minutes, dependent on the dose. The onset after inhalation is very fast (less than 45 seconds) and peak effects are reached within a minute. In the 1960s, DMT was known as a "businessman's trip" in the US because of the relatively short duration (and rapid onset) of action when inhaled.[61] DMT can be inhaled using a bong, typically when sandwiched between layers of plant matter, using a specially designed pipe, or by using an e-cigarette once it has been dissolved in propylene glycol and/or vegetable glycerin.[62] Some users have also started using vaporizers meant for cannabis extracts ("wax pens") for ease of temperature control when vaporizing crystals. A DMT-infused smoking blend is called Changa, and is typically used in pipes or other utensils meant for smoking dried plant matter.[citation needed]

Intravenous injection edit

In a study conducted from 1990 through 1995, University of New Mexico psychiatrist Rick Strassman found that some volunteers injected with high doses of DMT reported experiences with perceived alien entities. Usually, the reported entities were experienced as the inhabitants of a perceived independent reality that the subjects reported visiting while under the influence of DMT.[12]

Oral edit

See also: Ayahuasca and Pharmahuasca
 
Ayahuasca preparation

DMT is broken down by the enzyme monoamine oxidase through a process called deamination, and is quickly inactivated orally unless combined with a monoamine oxidase inhibitor (MAOI).[5] The traditional South American beverage ayahuasca is derived by boiling Banisteriopsis caapi with leaves of one or more plants containing DMT, such as Psychotria viridis, Psychotria carthagenensis, or Diplopterys cabrerana.[5] The Banisteriopsis caapi contains harmala alkaloids,[57] a highly active reversible inhibitor of monoamine oxidase A (RIMAs),[63] rendering the DMT orally active by protecting it from deamination.[5] A variety of different recipes are used to make the brew depending on the purpose of the ayahuasca session,[64] or local availability of ingredients. Two common sources of DMT in the western US are reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids but also contain gramine, which is toxic and difficult to separate. In addition, Jurema (Mimosa tenuiflora) shows evidence of DMT content: the pink layer in the inner rootbark of this small tree contains a high concentration of N,N-DMT.[citation needed]

Taken orally with an RIMA, DMT produces a long-lasting (over three hours), slow, deep metaphysical experience similar to that of psilocybin mushrooms, but more intense.[65]

The intensity of orally administered DMT depends on the type and dose of MAOI administered alongside it. When ingested with 120mg of harmine (a RIMA and member of the harmala alkaloids), 20mg of DMT was reported to have psychoactive effects by author and ethnobotanist Jonathan Ott. Ott reported that to produce a visionary state, the threshold oral dose was 30mg DMT alongside 120mg harmine.[66] This is not necessarily indicative of a standard dose, as dose-dependent effects may vary due to individual variations in drug metabolism.

History edit

See also: Ayahuasca § History

Naturally occurring substances (of both vegetable and animal origin) containing DMT have been used in South America since pre-Columbian times.[67][68]

DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske.[69][70] In general, its discovery as a natural product is credited to Brazilian chemist and microbiologist Oswaldo Gonçalves de Lima, who isolated an alkaloid he named nigerina (nigerine) from the root bark of Mimosa tenuiflora in 1946.[70][12][71] However, in a careful review of the case Jonathan Ott shows that the empirical formula for nigerine determined by Gonçalves de Lima, which notably contains an atom of oxygen, can match only a partial, "impure" or "contaminated" form of DMT.[66] It was only in 1959, when Gonçalves de Lima provided American chemists a sample of Mimosa tenuiflora roots, that DMT was unequivocally identified in this plant material.[66][72] Less ambiguous is the case of isolation and formal identification of DMT in 1955 in seeds and pods of Anadenanthera peregrina by a team of American chemists led by Evan Horning (1916–1993).[66][73] Since 1955, DMT has been found in a host of organisms: in at least fifty plant species belonging to ten families,[74] and in at least four animal species, including one gorgonian[75] and three mammalian species (including humans).[citation needed]

In terms of a scientific understanding, the hallucinogenic properties of DMT were not uncovered until 1956 by Hungarian chemist and psychiatrist Stephen Szara. In his paper “Dimethyltryptamin: Its Metabolism in Man; the Relation of its Psychotic Effect to the Serotonin Metabolism”, Szara employed synthetic DMT, synthesized by the method of Speeter and Anthony, which was then administered to 20 volunteers by intramuscular injection. Urine samples were collected from these volunteers for the identification of DMT metabolites.[76] This is considered to be the converging link between the chemical structure DMT to its cultural consumption as a psychoactive and religious sacrament.[77]

Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine Banisteriopsis caapi to make ayahuasca decoctions. In 1957, American chemists Francis Hochstein and Anita Paradies identified DMT in an "aqueous extract" of leaves of a plant they named Prestonia amazonicum [sic] and described as "commonly mixed" with B. caapi.[78] The lack of a proper botanical identification of Prestonia amazonica in this study led American ethnobotanist Richard Evans Schultes (1915–2001) and other scientists to raise serious doubts about the claimed plant identity.[79][80] The mistake likely led the writer William Burroughs to regard the DMT he experimented with in Tangier in 1961 as "Prestonia".[81] Better evidence was produced in 1965 by French pharmacologist Jacques Poisson, who isolated DMT as a sole alkaloid from leaves, provided and used by Aguaruna Indians, identified as having come from the vine Diplopterys cabrerana (then known as Banisteriopsis rusbyana).[80] Published in 1970, the first identification of DMT in the plant Psychotria viridis,[71] another common additive of ayahuasca, was made by a team of American researchers led by pharmacologist Ara der Marderosian.[82] Not only did they detect DMT in leaves of P. viridis obtained from Kaxinawá indigenous people, but they also were the first to identify it in a sample of an ayahuasca decoction, prepared by the same indigenous people.[71]

Legal status edit

International law edit

Main article: Convention on Psychotropic Substances

Internationally DMT is illegal, but ayahuasca and DMT brews and preparations are lawful. DMT is controlled by the Convention on Psychotropic Substances at the international level. The Convention makes it illegal to possess, buy, purchase, sell, to retail and to dispense without a licence.

By country and continent edit

See also: Legal status of ayahuasca by country

In some countries ayahuasca is a forbidden or controlled or regulated substance while in other countries it is not a controlled substance or its production, consumption, and sale, is allowed to various degrees.

Asia edit

  • Israel – DMT is an illegal substance; production, trade and possession are prosecuted as crimes.[83]
  • India – DMT is illegal to produce, transport, trade in or possess with a minimum prison or jail punishment of ten years.[84]

Europe edit

  • France – DMT, along with most of its plant sources, is classified as a stupéfiant (narcotic).
  • Germany – DMT is prohibited as a class I drug.[85]
  • Republic of Ireland – DMT is an illegal Schedule 1 drug under the Misuse of Drugs Acts.[86] An attempt in 2014 by a member of the Santo Daime church to gain a religious exemption to import the drug failed.[87]
  • Latvia — DMT is prohibited as a Schedule I drug.[88][89]
  • Netherlands – The drug is banned as it is classified as a List 1 Drug per the Opium Law. Production, trade and possession of DMT are prohibited.
  • Russia – Classified as a Schedule I narcotic, including its derivatives (see sumatriptan and zolmitriptan).[90]
  • Serbia – DMT, along with stereoisomers and salts is classified as List 4 (Psychotropic substances) substance according to Act on Control of Psychoactive Substances.
  • Sweden – DMT is considered a Schedule 1 drug. The Swedish supreme court concluded in 2018 that possession of processed plant material containing a significant amount of DMT is illegal. However, possession of unprocessed such plant material was ruled legal.[91][92]
  • United Kingdom – DMT is classified as a Class A drug.
  • Belgium – DMT cannot be possessed, sold, purchased or imported. Usage is not specifically prohibited, but since usage implies possession one could be prosecuted that way.[93]

North America edit

  • Canada – DMT is classified as a Schedule III drug under the Controlled Drugs and Substances Act, but is legal for religious groups to use.[94] In 2017 the Santo Daime Church Céu do Montréal received religious exemption to use Ayahuasca as a sacrament in their rituals.[95]

In December 2004, the Supreme Court lifted a stay, thereby allowing the Brazil-based União do Vegetal (UDV) church to use a decoction containing DMT in their Christmas services that year. This decoction is a tea made from boiled leaves and vines, known as hoasca within the UDV, and ayahuasca in different cultures. In Gonzales v. O Centro Espírita Beneficente União do Vegetal, the Supreme Court heard arguments on 1 November 2005, and unanimously ruled in February 2006 that the U.S. federal government must allow the UDV to import and consume the tea for religious ceremonies under the 1993 Religious Freedom Restoration Act.

In September 2008, the three Santo Daime churches filed suit in federal court to gain legal status to import DMT-containing ayahuasca tea. The case, Church of the Holy Light of the Queen v. Mukasey,[96] presided over by U.S. District Judge Owen M. Panner, was ruled in favor of the Santo Daime church. As of 21 March 2009, a federal judge says members of the church in Ashland can import, distribute and brew ayahuasca. Panner issued a permanent injunction barring the government from prohibiting or penalizing the sacramental use of "Daime tea". Panner's order said activities of The Church of the Holy Light of the Queen are legal and protected under freedom of religion. His order prohibits the federal government from interfering with and prosecuting church members who follow a list of regulations set out in his order.[97]

Oceania edit

  • New Zealand – DMT is classified as a Class A drug under the Misuse of Drugs Act 1975.[98][99]
  • Australia – DMT is listed as a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[100] A Schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO."[101] Between 2011 and 2012, the Australian federal government was considering changes to the Australian Criminal Code that would classify any plants containing any amount of DMT as "controlled plants".[102] DMT itself was already controlled under current laws. The proposed changes included other similar blanket bans for other substances, such as a ban on any and all plants containing mescaline or ephedrine. The proposal was not pursued after political embarrassment on realisation that this would make the official Floral Emblem of Australia, Acacia pycnantha (Golden Wattle), illegal.[citation needed] The Therapeutic Goods Administration and federal authority had considered a motion to ban the same, but this was withdrawn in May 2012 (as DMT may still hold potential entheogenic value to native and/or religious people).[103] Under the Misuse of Drugs Act 1981 6.0 g (3/16 oz) of DMT is considered enough to determine a court of trial and 2.0 g (1/16 oz) is considered intent to sell and supply.[104]

Chemistry edit

 
DMT crystals

DMT is commonly handled and stored as a hemifumarate,[105][106] as other DMT acid salts are extremely hygroscopic and will not readily crystallize. Its freebase form, although less stable than DMT hemifumarate, is favored by recreational users choosing to vaporize the chemical as it has a lower boiling point.[105]

Biosynthesis edit

 
Biosynthetic pathway for N,N-dimethyltryptamine

Dimethyltryptamine is an indole alkaloid derived from the shikimate pathway. Its biosynthesis is relatively simple and summarized in the adjacent picture. In plants, the parent amino acid L-tryptophan is produced endogenously where in animals L-tryptophan is an essential amino acid coming from diet. No matter the source of L-tryptophan, the biosynthesis begins with its decarboxylation by an aromatic amino acid decarboxylase (AADC) enzyme (step 1). The resulting decarboxylated tryptophan analog is tryptamine. Tryptamine then undergoes a transmethylation (step 2): the enzyme indolethylamine-N-methyltransferase (INMT) catalyzes the transfer of a methyl group from cofactor S-adenosylmethionine (SAM), via nucleophilic attack, to tryptamine. This reaction transforms SAM into S-adenosylhomocysteine (SAH), and gives the intermediate product N-methyltryptamine (NMT).[107][108] NMT is in turn transmethylated by the same process (step 3) to form the end product N,N-dimethyltryptamine. Tryptamine transmethylation is regulated by two products of the reaction: SAH,[109][110][111] and DMT[109][111] were shown ex vivo to be among the most potent inhibitors of rabbit INMT activity.

This transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of SAM methyl group with carbon-14 ((14C-CH3)SAM).[107][109][111][112][113]

Laboratory synthesis edit

DMT can be synthesized through several possible pathways from different starting materials. The two most commonly encountered synthetic routes are through the reaction of indole with oxalyl chloride followed by reaction with dimethylamine and reduction of the carbonyl functionalities with lithium aluminium hydride to form DMT.[114] The second commonly encountered route is through the N,N-dimethylation of tryptamine using formaldehyde followed by reduction with sodium cyanoborohydride or sodium triacetoxyborohydride. Sodium borohydride can be used but requires a larger excess of reagents and lower temperatures due to it having a higher selectivity for carbonyl groups as opposed to imines.[115] Procedures using sodium cyanoborohydride and sodium triacetoxyborohydride (presumably created in situ from cyanoborohydride though this may not be the case due to the presence of water or methanol) also result in the creation of cyanated tryptamine and beta-carboline byproducts of unknown toxicity while using sodium borohydride in absence of acid does not.[116] Bufotenine, a plant extract, can also be synthesized into DMT.[117]

Alternatively, an excess of methyl iodide or methyl p-toluenesulfonate and sodium carbonate can be used to over-methylate tryptamine, resulting in the creation of a quaternary ammonium salt, which is then dequaternized (demethylated) in ethanolamine to yield DMT. The same two-step procedure is used to synthesize other N,N-dimethylated compounds, such as 5-MeO-DMT.[118]

Clandestine manufacture edit

 
DMT during various stages of purification

In a clandestine setting, DMT is not typically synthesized due to the lack of availability of the starting materials, namely tryptamine and oxalyl chloride. Instead, it is more often extracted from plant sources using a nonpolar hydrocarbon solvent such as naphtha or heptane, and a base such as sodium hydroxide.[citation needed]

Alternatively, an acid-base extraction is sometimes used instead.

A variety of plants contain DMT at sufficient levels for being viable sources,[4] but specific plants such as Mimosa tenuiflora, Acacia acuminata and Acacia confusa are most often used.

The chemicals involved in the extraction are commonly available. The plant material may be illegal to procure in some countries. The end product (DMT) is illegal in most countries.

Evidence in mammals edit

Published in Science in 1961, Julius Axelrod found an N-methyltransferase enzyme capable of mediating biotransformation of tryptamine into DMT in a rabbit's lung.[107] This finding initiated a still ongoing scientific interest in endogenous DMT production in humans and other mammals.[108][44] From then on, two major complementary lines of evidence have been investigated: localization and further characterization of the N-methyltransferase enzyme, and analytical studies looking for endogenously produced DMT in body fluids and tissues.[108]

In 2013, researchers reported DMT in the pineal gland microdialysate of rodents.[119]

A study published in 2014 reported the biosynthesis of N,N-dimethyltryptamine (DMT) in the human melanoma cell line SK-Mel-147 including details on its metabolism by peroxidases.[120] It is assumed that more than half of the amount of DMT produced by the acidophilic cells of the pineal gland is secreted before and during death,[citation needed] the amount being 2.5–3.4 mg/kg. However, this claim by Strassman has been criticized by David Nichols who notes that DMT does not appear to be produced in any meaningful amount by the pineal gland. Removal or calcification of the pineal gland does not induce any of the symptoms caused by removal of DMT. The symptoms presented are consistent solely with reduction in melatonin, which is the pineal gland's known function. Nichols instead suggests that dynorphin and other endorphins are responsible for the reported euphoria experienced by patients during a near-death experience.[121] In 2014, researchers demonstrated the immunomodulatory potential of DMT and 5-MeO-DMT through the Sigma-1 receptor of human immune cells. This immunomodulatory activity may contribute to significant anti-inflammatory effects and tissue regeneration.[122]

Endogenous DMT edit

N,N-Dimethyltryptamine (DMT), a psychedelic compound identified endogenously in mammals, is biosynthesized by aromatic L-amino acid decarboxylase (AADC) and indolethylamine-N-methyltransferase (INMT). Studies have investigated brain expression of INMT transcript in rats and humans, coexpression of INMT and AADC mRNA in rat brain and periphery, and brain concentrations of DMT in rats. INMT transcripts were identified in the cerebral cortex, pineal gland, and choroid plexus of both rats and humans via in situ hybridization. Notably, INMT mRNA was colocalized with AADC transcript in rat brain tissues, in contrast to rat peripheral tissues where there existed little overlapping expression of INMT with AADC transcripts. Additionally, extracellular concentrations of DMT in the cerebral cortex of normal behaving rats, with or without the pineal gland, were similar to those of canonical monoamine neurotransmitters including serotonin. A significant increase of DMT levels in the rat visual cortex was observed following induction of experimental cardiac arrest, a finding independent of an intact pineal gland. These results show for the first time that the rat brain is capable of synthesizing and releasing DMT at concentrations comparable to known monoamine neurotransmitters and raise the possibility that this phenomenon may occur similarly in human brains.[123]

The first claimed detection of mammalian endogenous DMT was published in June 1965: German researchers F. Franzen and H. Gross report to have evidenced and quantified DMT, along with its structural analog bufotenin (5-HO-DMT), in human blood and urine.[124] In an article published four months later, the method used in their study was strongly criticized, and the credibility of their results challenged.[125]

Few of the analytical methods used prior to 2001 to measure levels of endogenously formed DMT had enough sensitivity and selectivity to produce reliable results.[126][127] Gas chromatography, preferably coupled to mass spectrometry (GC-MS), is considered a minimum requirement.[127] A study published in 2005[44] implements the most sensitive and selective method ever used to measure endogenous DMT:[128] liquid chromatography–tandem mass spectrometry with electrospray ionization (LC-ESI-MS/MS) allows for reaching limits of detection (LODs) 12 to 200 fold lower than those attained by the best methods employed in the 1970s. The data summarized in the table below are from studies conforming to the abovementioned requirements (abbreviations used: CSF = cerebrospinal fluid; LOD = limit of detection; n = number of samples; ng/L and ng/kg = nanograms (10−9 g) per litre, and nanograms per kilogram, respectively):

DMT in body fluids and tissues (NB: units have been harmonized)
Species Sample Results
Human Blood serum < LOD (n = 66)[44]
Blood plasma < LOD (n = 71)[44]  ♦  < LOD (n = 38); 1,000 & 10,600 ng/L (n = 2)[129]
Whole blood < LOD (n = 20); 50–790 ng/L (n = 20)[130]
Urine < 100 ng/L (n = 9)[44]  ♦  < LOD (n = 60); 160–540 ng/L (n = 5)[127]  ♦  Detected in n = 10 by GC-MS[131]
Feces < 50 ng/kg (n = 12); 130 ng/kg (n = 1)[44]
Kidney 15 ng/kg (n = 1)[44]
Lung 14 ng/kg (n = 1)[44]
Lumbar CSF 100,370 ng/L (n = 1); 2,330–7,210 ng/L (n = 3); 350 & 850 ng/L (n = 2)[45]
Rat Kidney 12 & 16 ng/kg (n = 2)[44]
Lung 22 & 12 ng/kg (n = 2)[44]
Liver 6 & 10 ng/kg (n = 2)[44]
Brain 10 & 15 ng/kg (n = 2)[44]  ♦  Measured in synaptic vesicular fraction[46]
Rabbit Liver < 10 ng/kg (n = 1)[44]

A 2013 study found DMT in microdialysate obtained from a rat's pineal gland, providing evidence of endogenous DMT in the mammalian brain.[119] In 2019 experiments showed that the rat brain is capable of synthesizing and releasing DMT. These results raise the possibility that this phenomenon may occur similarly in human brains.[48]

Detection in body fluids edit

DMT may be measured in blood, plasma or urine using chromatographic techniques as a diagnostic tool in clinical poisoning situations or to aid in the medicolegal investigation of suspicious deaths. In general, blood or plasma DMT levels in recreational users of the drug are in the 10–30 μg/L range during the first several hours post-ingestion.[citation needed] Less than 0.1% of an oral dose is eliminated unchanged in the 24-hour urine of humans.[132][133][clarification needed]

INMT edit

Before techniques of molecular biology were used to localize indolethylamine N-methyltransferase (INMT),[111][113] characterization and localization went on a par: samples of the biological material where INMT is hypothesized to be active are subject to enzyme assay. Those enzyme assays are performed either with a radiolabeled methyl donor like (14C-CH3)SAM to which known amounts of unlabeled substrates like tryptamine are added[108] or with addition of a radiolabeled substrate like (14C)NMT to demonstrate in vivo formation.[109][112] As qualitative determination of the radioactively tagged product of the enzymatic reaction is sufficient to characterize INMT existence and activity (or lack of), analytical methods used in INMT assays are not required to be as sensitive as those needed to directly detect and quantify the minute amounts of endogenously formed DMT. The essentially qualitative method thin layer chromatography (TLC) was thus used in a vast majority of studies.[108] Also, robust evidence that INMT can catalyze transmethylation of tryptamine into NMT and DMT could be provided with reverse isotope dilution analysis coupled to mass spectrometry for rabbit[134][135] and human[136] lung during the early 1970s.

Selectivity rather than sensitivity proved to be a challenge for some TLC methods with the discovery in 1974–1975 that incubating rat blood cells or brain tissue with (14C-CH3)SAM and NMT as substrate mostly yields tetrahydro-β-carboline derivatives,[108][109][137] and negligible amounts of DMT in brain tissue.[108] It is indeed simultaneously realized that the TLC methods used thus far in almost all published studies on INMT and DMT biosynthesis are incapable to resolve DMT from those tetrahydro-β-carbolines.[108] These findings are a blow for all previous claims of evidence of INMT activity and DMT biosynthesis in avian[138] and mammalian brain,[139][140] including in vivo,[141][142] as they all relied upon use of the problematic TLC methods:[108] their validity is doubted in replication studies that make use of improved TLC methods, and fail to evidence DMT-producing INMT activity in rat and human brain tissues.[143][144] Published in 1978, the last study attempting to evidence in vivo INMT activity and DMT production in brain (rat) with TLC methods finds biotransformation of radiolabeled tryptamine into DMT to be real but "insignificant".[145] Capability of the method used in this latter study to resolve DMT from tetrahydro-β-carbolines is questioned later.[109]

To localize INMT, a qualitative leap is accomplished with use of modern techniques of molecular biology, and of immunohistochemistry. In humans, a gene encoding INMT is determined to be located on chromosome 7.[113] Northern blot analyses reveal INMT messenger RNA (mRNA) to be highly expressed in rabbit lung,[111] and in human thyroid, adrenal gland, and lung.[113][146] Intermediate levels of expression are found in human heart, skeletal muscle, trachea, stomach, small intestine, pancreas, testis, prostate, placenta, lymph node, and spinal cord.[113][146] Low to very low levels of expression are noted in rabbit brain,[113] and human thymus, liver, spleen, kidney, colon, ovary, and bone marrow.[113][146] INMT mRNA expression is absent in human peripheral blood leukocytes, whole brain, and in tissue from 7 specific brain regions (thalamus, subthalamic nucleus, caudate nucleus, hippocampus, amygdala, substantia nigra, and corpus callosum).[113][146] Immunohistochemistry showed INMT to be present in large amounts in glandular epithelial cells of small and large intestines. In 2011, immunohistochemistry revealed the presence of INMT in primate nervous tissue including retina, spinal cord motor neurons, and pineal gland.[49] A 2020 study using in-situ hybridization, a far more accurate tool than the northern blot analysis, found mRNA coding for INMT expressed in the human cerebral cortex, choroid plexus, and pineal gland.[48]

Pharmacology edit

Pharmacokinetics edit

DMT peak level concentrations (Cmax) measured in whole blood after intramuscular (IM) injection (0.7 mg/kg, n = 11)[147] and in plasma following intravenous (IV) administration (0.4 mg/kg, n = 10)[21] of fully psychedelic doses are in the range of around 14 to 154 μg/L and 32 to 204 μg/L, respectively. The corresponding molar concentrations of DMT are therefore in the range of 0.074–0.818 μmol/L in whole blood and 0.170–1.08 μmol in plasma. However, several studies have described active transport and accumulation of DMT into rat and dog brains following peripheral administration.[148][149][150][151][152] Similar active transport, and accumulation processes likely occur in human brains and may concentrate DMT in brain by several-fold or more (relatively to blood), resulting in local concentrations in the micromolar or higher range. Such concentrations would be commensurate with serotonin brain tissue concentrations, which have been consistently determined to be in the 1.5–4 μmol/L range.[153][154]

Closely coextending with peak psychedelic effects, mean time to reach peak concentrations (Tmax) was determined to be 10–15 minutes in whole blood after IM injection,[147] and 2 minutes in plasma after IV administration.[21] When taken orally mixed in an ayahuasca decoction, and in freeze-dried ayahuasca gel caps, DMT Tmax is considerably delayed: 107.59 ± 32.5 minutes,[155] and 90–120 minutes,[156] respectively. The pharmacokinetics for vaporizing DMT have not been studied or reported.

Neurogenesis edit

See also: 5-MeO-DMT § Neurogenesis, Ayahuasca § Neurogenesis, and Banisteriopsis caapi § Neurogenesis

In September 2020, an in vitro and in vivo study showed that DMT present in the ayahuasca infusion promotes neurogenesis.[157]

Pharmacodynamics edit

DMT binds non-selectively with affinities below 0.6 μmol/L to the following serotonin receptors: 5-HT1A,[158][159][160] 5-HT1B,[158][161] 5-HT1D,[158][160][161] 5-HT2A,[158][160][161][162] 5-HT2B,[158][161] 5-HT2C,[158][161][162] 5-HT6,[158][161] and 5-HT7.[158][161] An agonist action has been determined at 5-HT1A,[159] 5-HT2A and 5-HT2C.[158][161][162] Its efficacies at other serotonin receptors remain to be determined. Of special interest will be the determination of its efficacy at human 5-HT2B receptor as two in vitro assays evidenced DMT's high affinity for this receptor: 0.108 µmol/L[161] and 0.184 µmol/L.[158] This may be of importance because chronic or frequent uses of serotonergic drugs showing preferential high affinity and clear agonism at 5-HT2B receptor have been causally linked to valvular heart disease.[163][164][165]

It has also been shown to possess affinity for the dopamine D1, α1-adrenergic, α2-adrenergic, imidazoline-1, and σ1 receptors.[160][161][166] Converging lines of evidence established activation of the σ1 receptor at concentrations of 50–100 μmol/L.[167] Its efficacies at the other receptor binding sites are unclear. It has also been shown in vitro to be a substrate for the cell-surface serotonin transporter (SERT) expressed in human platelets, and the rat vesicular monoamine transporter 2 (VMAT2), which was transiently expressed in fall armyworm Sf9 cells. DMT inhibited SERT-mediated serotonin uptake into platelets at an average concentration of 4.00 ± 0.70 µmol/L and VMAT2-mediated serotonin uptake at an average concentration of 93 ± 6.8 µmol/L.[168]

As with other so-called "classical hallucinogens",[169] a large part of DMT psychedelic effects can be attributed to a functionally selective activation of the 5-HT2A receptor.[21][158][170][171][172][173][174] DMT concentrations eliciting 50% of its maximal effect (half maximal effective concentration = EC50) at the human 5-HT2A receptor in vitro are in the 0.118–0.983 µmol/L range.[158][161][162][175] This range of values coincides well with the range of concentrations measured in blood and plasma after administration of a fully psychedelic dose (see Pharmacokinetics).

As DMT has been shown to have slightly better efficacy (EC50) at human serotonin 2C receptor than at the 2A receptor,[161][162] 5-HT2C is also likely implicated in DMT's overall effects.[171][176] Other receptors such as 5-HT1A[160][171][173] and σ1[167][177] may also play a role.

In 2009, it was hypothesized that DMT may be an endogenous ligand for the σ1 receptor.[167][177] The concentration of DMT needed for σ1 activation in vitro (50–100 µmol/L) is similar to the behaviorally active concentration measured in mouse brain of approximately 106 µmol/L[178] This is minimally 4 orders of magnitude higher than the average concentrations measured in rat brain tissue or human plasma under basal conditions (see Endogenous DMT), so σ1 receptors are likely to be activated only under conditions of high local DMT concentrations. If DMT is stored in synaptic vesicles,[168] such concentrations might occur during vesicular release. To illustrate, while the average concentration of serotonin in brain tissue is in the 1.5–4 µmol/L range,[153][154] the concentration of serotonin in synaptic vesicles was measured at 270 mM.[179] Following vesicular release, the resulting concentration of serotonin in the synaptic cleft, to which serotonin receptors are exposed, is estimated to be about 300 µmol/L. Thus, while in vitro receptor binding affinities, efficacies, and average concentrations in tissue or plasma are useful, they are not likely to predict DMT concentrations in the vesicles or at synaptic or intracellular receptors. Under these conditions, notions of receptor selectivity are moot, and it seems probable that most of the receptors identified as targets for DMT (see above) participate in producing its psychedelic effects.

Binding sites Binding affinity Ki (μM)[180]
5-HT1A 0.075
5-HT2A 0.237
5-HT2C 0.424
D1 6
D2 3
D3 6.3
α1A 1.3
α2A 2.1
TAAR1 2.2
H1 0.22
SERT 6
DAT 22
NET 6.5

Society and culture edit

Black market edit

Electronic cigarette cartridges filled with DMT started to be sold on the black market in 2018.[181]

See also edit

References edit

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February 16, 2024
dimethyltryptamine, redirects, here, other, uses, disambiguation, this, article, needs, more, reliable, medical, references, verification, relies, heavily, primary, sources, please, review, contents, article, appropriate, references, unsourced, poorly, sourced. DMT redirects here For other uses see DMT disambiguation This article needs more reliable medical references for verification or relies too heavily on primary sources Please review the contents of the article and add the appropriate references if you can Unsourced or poorly sourced material may be challenged and removed Find sources N N Dimethyltryptamine news newspapers books scholar JSTOR June 2017 N N Dimethyltryptamine DMT or N N DMT is a substituted tryptamine that occurs in many plants and animals including humans and which is both a derivative and a structural analog of tryptamine 4 DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen 5 N N DimethyltryptamineClinical dataRoutes ofadministrationOral with an MAOI vaporized insufflated rectal IM IVATC codeNoneLegal statusLegal statusAU S9 Prohibited substance BR Class F2 Prohibited psychotropics 1 CA Schedule III DE Anlage I Authorized scientific use only UK Class A US Schedule I UN Psychotropic Schedule IPharmacokinetic dataElimination half life9 12 minutesIdentifiersIUPAC name 2 1H Indol 3 yl N N dimethylethanamineCAS Number61 50 7 YPubChem CID6089IUPHAR BPS141DrugBankDB01488 YChemSpider5864 YUNIIWUB601BHAAKEGGC08302 YChEBICHEBI 28969 YChEMBLChEMBL12420 YCompTox Dashboard EPA DTXSID60110053ECHA InfoCard100 000 463Chemical and physical dataFormulaC 12H 16N 2Molar mass188 274 g mol 13D model JSmol Interactive imageDensity1 099 g cm3Melting point40 C 104 F Boiling point160 C 320 F at 0 6 Torr 80 Pa 2 also reported as80 135 C 176 275 F at 0 03 Torr 4 0 Pa 3 SMILES CN CCC1 CNC2 C1C CC C2 CInChI InChI 1S C12H16N2 c1 14 2 8 7 10 9 13 12 6 4 3 5 11 10 12 h3 6 9 13H 7 8H2 1 2H3 YKey DMULVCHRPCFFGV UHFFFAOYSA N Y verify DMT has a rapid onset intense effects and a relatively short duration of action For those reasons DMT was known as the businessman s trip during the 1960s in the United States as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms 6 DMT can be inhaled ingested or injected and its effects depend on the dose as well as the mode of administration When inhaled or injected the effects last a short period of time about five to 15 minutes Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor MAOI such as the ayahuasca brew of many native Amazonian tribes 7 DMT can produce vivid projections of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms 8 DMT is a functional analog and structural analog of other psychedelic tryptamines such as O acetylpsilocin 4 AcO DMT psilocybin 4 PO DMT psilocin 4 HO DMT O methylbufotenin 5 MeO DMT and bufotenin 5 HO DMT Parts of the structure of DMT occur within some important biomolecules like serotonin and melatonin making them structural analogs of DMT Contents 1 Human consumption 1 1 Clinical use research 1 2 Neuropharmacology 2 Effects 2 1 Subjective psychedelic experiences 2 1 1 Reported encounters with external entities 2 1 2 Near death experience 2 2 Physiological response 2 3 Conjecture regarding endogenous effects 3 Adverse effects 3 1 Mental disorders 3 2 Addiction and dependence liability 3 3 Tolerance 3 4 Long term use 3 5 Drug interactions 4 Routes of administration 4 1 Inhalation 4 2 Intravenous injection 4 3 Oral 5 History 6 Legal status 6 1 International law 6 2 By country and continent 6 2 1 Asia 6 2 2 Europe 6 2 3 North America 6 2 4 Oceania 7 Chemistry 7 1 Biosynthesis 7 2 Laboratory synthesis 7 3 Clandestine manufacture 7 4 Evidence in mammals 7 4 1 Endogenous DMT 7 5 Detection in body fluids 7 5 1 INMT 8 Pharmacology 8 1 Pharmacokinetics 8 1 1 Neurogenesis 8 2 Pharmacodynamics 9 Society and culture 9 1 Black market 10 See also 11 References 12 External linksHuman consumption editThe examples and perspective in this section may not represent a worldwide view of the subject You may improve this section discuss the issue on the talk page or create a new section as appropriate December 2022 Learn how and when to remove this template message DMT is produced in many species of plants often in conjunction with its close chemical relatives 5 methoxy N N dimethyltryptamine 5 MeO DMT and bufotenin 5 OH DMT 9 DMT containing plants are commonly used in indigenous Amazonian shamanic practices It is usually one of the main active constituents of the drink ayahuasca 10 5 however ayahuasca is sometimes brewed with plants that do not produce DMT It occurs as the primary psychoactive alkaloid in several plants including Mimosa tenuiflora Diplopterys cabrerana and Psychotria viridis DMT is found as a minor alkaloid in snuff made from Virola bark resin in which 5 MeO DMT is the main active alkaloid 9 DMT is also found as a minor alkaloid in bark pods and beans of Anadenanthera peregrina and Anadenanthera colubrina used to make Yopo and Vilca snuff in which bufotenin is the main active alkaloid 9 11 Psilocin and psilocybin the main psychoactive compounds in psilocybin mushrooms are structurally similar to DMT The psychotropic effects of DMT were first studied scientifically by the Hungarian chemist and psychologist Stephen Szara who performed research with volunteers in the mid 1950s Szara who later worked for the United States National Institutes of Health had turned his attention to DMT after his order for LSD from the Swiss company Sandoz Laboratories was rejected on the grounds that the powerful psychotropic could be dangerous in the hands of a communist country 12 DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor such as a reversible inhibitor of monoamine oxidase A RIMA for example harmaline 5 Without a MAOI the body quickly metabolizes orally administered DMT and it therefore has no hallucinogenic effect unless the dose exceeds the body s monoamine oxidase s metabolic capacity Other means of consumption such as vaporizing injecting or insufflating the drug can produce powerful hallucinations for a short time usually less than half an hour as the DMT reaches the brain before it can be metabolized by the body s natural monoamine oxidase Taking an MAOI prior to vaporizing or injecting DMT prolongs and enhances the effects 8 Clinical use research edit Dimethyltryptamine DMT an endogenous ligand of sigma 1 receptors Sig 1Rs acts against systemic hypoxia Research demonstrates DMT reduces the number of apoptotic and ferroptotic cells in mammalian forebrain and supports astrocyte survival in an ischemic environment According to these data DMT may be considered as adjuvant pharmacological therapy in the management of acute cerebral ischemia 13 DMT is studied as a potential treatment for Parkinson s disease in a Phase 1 2 clinical trial 14 SPL026 DMT fumarate is currently undergoing phase II clinical trials investigating its use alongside supportive psychotherapy as a potential treatment for major depressive disorder 15 Additionally a safety study is underway to investigate the effects of combining SSRIs with SPL026 16 Neuropharmacology edit Recently researchers discovered that N N dimethyltryptamine is a potent psychoplastogen a compound capable of promoting rapid and sustained neuroplasticity that may have wide ranging therapeutic benefit 17 Quantities of dimethyltryptamine and O methylbufotenin were found present in the cerebrospinal fluid of humans in a psychiatric study 18 Effects editSee also Ayahuasca Effects Subjective psychedelic experiences edit Subjective experiences of DMT includes profound time dilatory visual auditory tactile and proprioceptive distortions and hallucinations and other experiences that by most firsthand accounts defy verbal or visual description 19 Examples include perceiving hyperbolic geometry or seeing Escher like impossible objects 20 Several scientific experimental studies have tried to measure subjective experiences of altered states of consciousness induced by drugs under highly controlled and safe conditions Rick Strassman and his colleagues conducted a five year long DMT study at the University of New Mexico in the 1990s 21 The results provided insight about the quality of subjective psychedelic experiences In this study participants received the DMT dosage via intravenous injection and the findings suggested that different psychedelic experiences can occur depending on the level of dosage Lower doses 0 01 and 0 05 mg kg produced some aesthetic and emotional responses but not hallucinogenic experiences e g 0 05 mg kg had mild mood elevating and calming properties 21 In contrast responses produced by higher doses 0 2 and 0 4 mg kg researchers labeled as hallucinogenic that elicited intensely colored rapidly moving display of visual images formed abstract or both Comparing to other sensory modalities the most affected was the visual Participants reported visual hallucinations fewer auditory hallucinations and specific physical sensations progressing to a sense of bodily dissociation as well as to experiences of euphoria calm fear and anxiety 21 These dose dependent effects match well with anonymously posted trip reports online where users report breakthroughs clarification needed above certain doses 22 23 24 Strassman also stressed the importance of the context where the drug has been taken He claimed that DMT has no beneficial effects of itself rather the context when and where people take it plays an important role 12 21 It appears that DMT can induce a state or feeling where the person believes to communicate with other intelligent lifeforms see machine elves High doses of DMT produce a state that involves a sense of another intelligence that people sometimes describe as super intelligent but emotionally detached 21 A 1995 study by Adolf Dittrich and Daniel Lamparter found that the DMT induced altered state of consciousness ASC is strongly influenced by habitual rather than situative factors In the study researchers used three dimensions of the APZ questionnaire to examine ASC The first dimension oceanic boundlessness OB refers to dissolution of ego boundaries and is mostly associated with positive emotions 25 The second dimension anxious ego dissolution AED represents a disordering of thoughts and decreases in autonomy and self control Last visionary restructuralization VR refers to auditory visual illusions and hallucinations 26 Results showed strong effects within the first and third dimensions for all conditions especially with DMT and suggested strong intrastability of elicited reactions independently of the condition for the OB and VR scales 25 Reported encounters with external entities edit Entities perceived during DMT inebriation have been represented in diverse forms of psychedelic art The term machine elf was coined by ethnobotanist Terence McKenna for the entities he encountered in DMT hyperspace also using terms like fractal elves or self transforming machine elves 27 28 McKenna first encountered the machine elves after smoking DMT in Berkeley in 1965 His subsequent speculations regarding the hyperdimensional space in which they were encountered have inspired a great many artists and musicians and the meaning of DMT entities has been a subject of considerable debate among participants in a networked cultural underground enthused by McKenna s effusive accounts of DMT hyperspace 29 Cliff Pickover has also written about the machine elf experience in the book Sex Drugs Einstein amp Elves 7 Strassman noted similarities between self reports of his DMT study participants encounters with these entities and mythological descriptions of figures such as Ḥayyot haq Qodesh in ancient religions including both angels and demons 30 Strassman also argues for a similarity in his study participants descriptions of mechanized wheels gears and machinery in these encounters with those described in visions of encounters with the Living Creatures and Ophanim of the Hebrew Bible noting they may stem from a common neuropsychopharmacological experience 30 Strassman argues that the more positive of the external entities encountered in DMT experiences should be understood as analogous to certain forms of angels The medieval Jewish philosophers whom I rely upon for understanding the Hebrew Bible text and its concept of prophecy portray angels as God s intermediaries That is they perform a certain function for God Within the context of my DMT research I believe that the beings that volunteers see could be conceived of as angelic that is previously invisible incorporeal spiritual forces that are engarbed or enclothed in a particular form determined by the psychological and spiritual development of the volunteers bringing a particular message or experience to that volunteer 31 Strassman s experimental participants also note that some other entities can subjectively resemble creatures more like insects and aliens 32 As a result Strassman writes these experiences among his experimental participants also left me feeling confused and concerned about where the spirit molecule was leading us It was at this point that I began to wonder if I was getting in over my head with this research 33 Hallucinations of strange creatures had been reported by Stephen Szara in a 1958 study in psychotic patients in which he described how one of his subjects under the influence of DMT had experienced strange creatures dwarves or something at the beginning of a DMT trip 34 35 Other researchers of the entities seemingly encountered by DMT users describe them as entities or beings in humanoid as well as animal form with descriptions of little people being common non human gnomes elves imps etc 36 37 Strassman and others have speculated that this form of hallucination may be the cause of alien abduction and extraterrestrial encounter experiences which may occur through endogenously occurring DMT 38 39 Likening them to descriptions of rattling and chattering auditory phenomena described in encounters with the Hayyoth in the Book of Ezekiel Rick Strassman notes that participants in his studies when reporting encounters with the alleged entities have also described loud auditory hallucinations such as one subject reporting typically the elves laughing or talking at high volume chattering twittering 30 Near death experience edit A 2018 study found significant relationships between a DMT experience and a near death experience 40 A 2019 large scale study pointed that ketamine Salvia divinorum and DMT and other classical psychedelic substances may be linked to near death experiences due to the semantic similarity of reports associated with the use of psychoactive compounds and NDE narratives but the study concluded that with the current data it is neither possible to corroborate nor refute the hypothesis that the release of an endogenous ketamine like neuroprotective agent underlies NDE phenomenology 41 Physiological response edit According to a dose response study in human subjects dimethyltryptamine administered intravenously slightly elevated blood pressure heart rate pupil diameter and rectal temperature in addition to elevating blood concentrations of beta endorphin corticotropin cortisol and prolactin growth hormone blood levels rise equally in response to all doses of DMT and melatonin levels were unaffected 21 Conjecture regarding endogenous effects edit In the 1950s the endogenous production of psychoactive agents was considered to be a potential explanation for the hallucinatory symptoms of some psychiatric diseases this is known as the transmethylation hypothesis 42 Several speculative and yet untested hypotheses suggest that endogenous DMT is produced in the human brain and is involved in certain psychological and neurological states 43 DMT is naturally occurring in small amounts in rat brain human cerebrospinal fluid and other tissues of humans and other mammals 44 45 46 47 Further mRNA for the enzyme necessary for the production of DMT INMT are expressed in the human cerebral cortex choroid plexus and pineal gland suggesting an endogenous role in the human brain 48 In 2011 Nicholas V Cozzi of the University of Wisconsin School of Medicine and Public Health concluded that INMT an enzyme that is associated with the biosynthesis of DMT and endogenous hallucinogens is present in the primate rhesus macaque pineal gland retinal ganglion neurons and spinal cord 49 Neurobiologist Andrew Gallimore 2013 suggested that while DMT might not have a modern neural function it may have been an ancestral neuromodulator once secreted in psychedelic concentrations during REM sleep a function now lost 36 Adverse effects editMental disorders edit DMT may trigger psychological reactions known colloquially as a bad trip such as intense fear paranoia anxiety panic attacks and substance induced psychosis particularly in predisposed individuals 50 51 In fact these experiences are an essential part of the process for the subject whereby they face an overcome these fears and as a result gain significant psychological benefits like enhanced confidence self worth and self reliance Research now supports the theory that the more of this type of experience that occurs during a trip the more benefit that the subject enjoys post trip This is why set setting and post trip integration are all of paramount importance Its also important to bear in mind the vad trip experience is short lived and transitory and the subject is never in any real danger Such experiences are often referred to as ego death Addiction and dependence liability edit DMT like other serotonergic psychedelics is considered to be non addictive with low abuse potential 19 A study examining substance use disorder for DSM IV reported that almost no hallucinogens produced dependence unlike psychoactive drugs of other classes such as stimulants and depressants 50 52 At present there have been no studies that report drug withdrawal syndrome with termination of DMT and dependence potential of DMT and the risk of sustained psychological disturbance may be minimal when used infrequently however the physiological dependence potential of DMT and ayahuasca has not yet been documented convincingly 53 Tolerance edit Unlike other classical psychedelics studies report that DMT did not exhibit tolerance upon repeated administration of twice a day sessions separated by 5 hours for 5 consecutive days field reports suggests a refractory period of only 15 to 30 minutes while the plasma levels of DMT was nearly undetectable 30 minutes after intravenous administration 54 Another study of four closely spaced DMT infusion sessions with 30 minute intervals also suggests no tolerance buildup to the psychological effects of the compound while heart rate responses and neuroendocrine effects were diminished with repeated administration 54 A fully hallucinogenic dose of DMT did not demonstrate cross tolerance to human subjects who are highly tolerant to LSD 55 researches suggest that DMT exhibits unique pharmacological properties compared to other classical psychedelics 54 Long term use edit There have been no serious adverse effects reported on long term use of DMT apart from acute cardiovascular events 51 Repeated and one time administration of DMT produces marked changes in the cardiovascular system 51 with an increase in systolic and diastolic blood pressure although the changes were not statistically significant a robust trend towards significance was observed for systolic blood pressure at high doses 56 Drug interactions edit DMT is inactive when ingested orally due to metabolism by MAO and DMT containing drinks such as ayahuasca have been found to contain MAOIs in particular harmine and harmaline 56 Life threatening lethalities such as serotonin syndrome SS may occur when MAOIs are combined with certain serotonergic medications such as SSRI antidepressants 57 50 Serotonin syndrome has also been reported with tricyclic antidepressants opiates analgesic and antimigraine drugs it is advised to exercise caution when an individual had used dextromethorphan DXM MDMA ginseng or St John s wort recently 50 Chronic use of SSRIs TCAs and MAOIs diminish subjective effects of psychedelics due to presumed SSRI induced 5 HT2A receptors downregulation and MAOI induced 5 HT2A receptor desensitization 58 145 The interaction between psychedelics and antipsychotics and anticonvulsant are not well documented however reports reveal that co use of psychedelics with mood stabilizers such as lithium may provoke seizure and dissociative effects in individuals with bipolar disorder 59 58 146 Routes of administration editInhalation edit nbsp Free base DMT extracted from Mimosa hostilis root bark left vape cartridge made with freebase DMT extract right A standard dose for vaporized DMT is 20 60 milligrams depending highly on the efficiency of vaporization as well as body weight and personal variation 60 medical citation needed In general this is inhaled in a few successive breaths but lower doses can be used if the user can inhale it in fewer breaths ideally one The effects last for a short period of time usually 5 to 15 minutes dependent on the dose The onset after inhalation is very fast less than 45 seconds and peak effects are reached within a minute In the 1960s DMT was known as a businessman s trip in the US because of the relatively short duration and rapid onset of action when inhaled 61 DMT can be inhaled using a bong typically when sandwiched between layers of plant matter using a specially designed pipe or by using an e cigarette once it has been dissolved in propylene glycol and or vegetable glycerin 62 Some users have also started using vaporizers meant for cannabis extracts wax pens for ease of temperature control when vaporizing crystals A DMT infused smoking blend is called Changa and is typically used in pipes or other utensils meant for smoking dried plant matter citation needed Intravenous injection edit In a study conducted from 1990 through 1995 University of New Mexico psychiatrist Rick Strassman found that some volunteers injected with high doses of DMT reported experiences with perceived alien entities Usually the reported entities were experienced as the inhabitants of a perceived independent reality that the subjects reported visiting while under the influence of DMT 12 Oral edit See also Ayahuasca and Pharmahuasca nbsp Ayahuasca preparationDMT is broken down by the enzyme monoamine oxidase through a process called deamination and is quickly inactivated orally unless combined with a monoamine oxidase inhibitor MAOI 5 The traditional South American beverage ayahuasca is derived by boiling Banisteriopsis caapi with leaves of one or more plants containing DMT such as Psychotria viridis Psychotria carthagenensis or Diplopterys cabrerana 5 The Banisteriopsis caapi contains harmala alkaloids 57 a highly active reversible inhibitor of monoamine oxidase A RIMAs 63 rendering the DMT orally active by protecting it from deamination 5 A variety of different recipes are used to make the brew depending on the purpose of the ayahuasca session 64 or local availability of ingredients Two common sources of DMT in the western US are reed canary grass Phalaris arundinacea and Harding grass Phalaris aquatica These invasive grasses contain low levels of DMT and other alkaloids but also contain gramine which is toxic and difficult to separate In addition Jurema Mimosa tenuiflora shows evidence of DMT content the pink layer in the inner rootbark of this small tree contains a high concentration of N N DMT citation needed Taken orally with an RIMA DMT produces a long lasting over three hours slow deep metaphysical experience similar to that of psilocybin mushrooms but more intense 65 The intensity of orally administered DMT depends on the type and dose of MAOI administered alongside it When ingested with 120mg of harmine a RIMA and member of the harmala alkaloids 20mg of DMT was reported to have psychoactive effects by author and ethnobotanist Jonathan Ott Ott reported that to produce a visionary state the threshold oral dose was 30mg DMT alongside 120mg harmine 66 This is not necessarily indicative of a standard dose as dose dependent effects may vary due to individual variations in drug metabolism History editSee also Ayahuasca History Naturally occurring substances of both vegetable and animal origin containing DMT have been used in South America since pre Columbian times 67 68 DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske 69 70 In general its discovery as a natural product is credited to Brazilian chemist and microbiologist Oswaldo Goncalves de Lima who isolated an alkaloid he named nigerina nigerine from the root bark of Mimosa tenuiflora in 1946 70 12 71 However in a careful review of the case Jonathan Ott shows that the empirical formula for nigerine determined by Goncalves de Lima which notably contains an atom of oxygen can match only a partial impure or contaminated form of DMT 66 It was only in 1959 when Goncalves de Lima provided American chemists a sample of Mimosa tenuiflora roots that DMT was unequivocally identified in this plant material 66 72 Less ambiguous is the case of isolation and formal identification of DMT in 1955 in seeds and pods of Anadenanthera peregrina by a team of American chemists led by Evan Horning 1916 1993 66 73 Since 1955 DMT has been found in a host of organisms in at least fifty plant species belonging to ten families 74 and in at least four animal species including one gorgonian 75 and three mammalian species including humans citation needed In terms of a scientific understanding the hallucinogenic properties of DMT were not uncovered until 1956 by Hungarian chemist and psychiatrist Stephen Szara In his paper Dimethyltryptamin Its Metabolism in Man the Relation of its Psychotic Effect to the Serotonin Metabolism Szara employed synthetic DMT synthesized by the method of Speeter and Anthony which was then administered to 20 volunteers by intramuscular injection Urine samples were collected from these volunteers for the identification of DMT metabolites 76 This is considered to be the converging link between the chemical structure DMT to its cultural consumption as a psychoactive and religious sacrament 77 Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine Banisteriopsis caapi to make ayahuasca decoctions In 1957 American chemists Francis Hochstein and Anita Paradies identified DMT in an aqueous extract of leaves of a plant they named Prestonia amazonicum sic and described as commonly mixed with B caapi 78 The lack of a proper botanical identification of Prestonia amazonica in this study led American ethnobotanist Richard Evans Schultes 1915 2001 and other scientists to raise serious doubts about the claimed plant identity 79 80 The mistake likely led the writer William Burroughs to regard the DMT he experimented with in Tangier in 1961 as Prestonia 81 Better evidence was produced in 1965 by French pharmacologist Jacques Poisson who isolated DMT as a sole alkaloid from leaves provided and used by Aguaruna Indians identified as having come from the vine Diplopterys cabrerana then known as Banisteriopsis rusbyana 80 Published in 1970 the first identification of DMT in the plant Psychotria viridis 71 another common additive of ayahuasca was made by a team of American researchers led by pharmacologist Ara der Marderosian 82 Not only did they detect DMT in leaves of P viridis obtained from Kaxinawa indigenous people but they also were the first to identify it in a sample of an ayahuasca decoction prepared by the same indigenous people 71 Legal status editInternational law edit Main article Convention on Psychotropic Substances Internationally DMT is illegal but ayahuasca and DMT brews and preparations are lawful DMT is controlled by the Convention on Psychotropic Substances at the international level The Convention makes it illegal to possess buy purchase sell to retail and to dispense without a licence By country and continent edit See also Legal status of ayahuasca by country In some countries ayahuasca is a forbidden or controlled or regulated substance while in other countries it is not a controlled substance or its production consumption and sale is allowed to various degrees Asia edit Israel DMT is an illegal substance production trade and possession are prosecuted as crimes 83 India DMT is illegal to produce transport trade in or possess with a minimum prison or jail punishment of ten years 84 Europe edit France DMT along with most of its plant sources is classified as a stupefiant narcotic Germany DMT is prohibited as a class I drug 85 Republic of Ireland DMT is an illegal Schedule 1 drug under the Misuse of Drugs Acts 86 An attempt in 2014 by a member of the Santo Daime church to gain a religious exemption to import the drug failed 87 Latvia DMT is prohibited as a Schedule I drug 88 89 Netherlands The drug is banned as it is classified as a List 1 Drug per the Opium Law Production trade and possession of DMT are prohibited Russia Classified as a Schedule I narcotic including its derivatives see sumatriptan and zolmitriptan 90 Serbia DMT along with stereoisomers and salts is classified as List 4 Psychotropic substances substance according to Act on Control of Psychoactive Substances Sweden DMT is considered a Schedule 1 drug The Swedish supreme court concluded in 2018 that possession of processed plant material containing a significant amount of DMT is illegal However possession of unprocessed such plant material was ruled legal 91 92 United Kingdom DMT is classified as a Class A drug Belgium DMT cannot be possessed sold purchased or imported Usage is not specifically prohibited but since usage implies possession one could be prosecuted that way 93 North America edit Canada DMT is classified as a Schedule III drug under the Controlled Drugs and Substances Act but is legal for religious groups to use 94 In 2017 the Santo Daime Church Ceu do Montreal received religious exemption to use Ayahuasca as a sacrament in their rituals 95 United States DMT is classified in the United States as a Schedule I drug under the Controlled Substances Act of 1970 In December 2004 the Supreme Court lifted a stay thereby allowing the Brazil based Uniao do Vegetal UDV church to use a decoction containing DMT in their Christmas services that year This decoction is a tea made from boiled leaves and vines known as hoasca within the UDV and ayahuasca in different cultures In Gonzales v O Centro Espirita Beneficente Uniao do Vegetal the Supreme Court heard arguments on 1 November 2005 and unanimously ruled in February 2006 that the U S federal government must allow the UDV to import and consume the tea for religious ceremonies under the 1993 Religious Freedom Restoration Act In September 2008 the three Santo Daime churches filed suit in federal court to gain legal status to import DMT containing ayahuasca tea The case Church of the Holy Light of the Queen v Mukasey 96 presided over by U S District Judge Owen M Panner was ruled in favor of the Santo Daime church As of 21 March 2009 a federal judge says members of the church in Ashland can import distribute and brew ayahuasca Panner issued a permanent injunction barring the government from prohibiting or penalizing the sacramental use of Daime tea Panner s order said activities of The Church of the Holy Light of the Queen are legal and protected under freedom of religion His order prohibits the federal government from interfering with and prosecuting church members who follow a list of regulations set out in his order 97 Oceania edit New Zealand DMT is classified as a Class A drug under the Misuse of Drugs Act 1975 98 99 Australia DMT is listed as a Schedule 9 prohibited substance in Australia under the Poisons Standard October 2015 100 A Schedule 9 drug is outlined in the Poisons Act 1964 as Substances which may be abused or misused the manufacture possession sale or use of which should be prohibited by law except when required for medical or scientific research or for analytical teaching or training purposes with approval of the CEO 101 Between 2011 and 2012 the Australian federal government was considering changes to the Australian Criminal Code that would classify any plants containing any amount of DMT as controlled plants 102 DMT itself was already controlled under current laws The proposed changes included other similar blanket bans for other substances such as a ban on any and all plants containing mescaline or ephedrine The proposal was not pursued after political embarrassment on realisation that this would make the official Floral Emblem of Australia Acacia pycnantha Golden Wattle illegal citation needed The Therapeutic Goods Administration and federal authority had considered a motion to ban the same but this was withdrawn in May 2012 as DMT may still hold potential entheogenic value to native and or religious people 103 Under the Misuse of Drugs Act 1981 6 0 g 3 16 oz of DMT is considered enough to determine a court of trial and 2 0 g 1 16 oz is considered intent to sell and supply 104 Chemistry edit nbsp DMT crystalsDMT is commonly handled and stored as a hemifumarate 105 106 as other DMT acid salts are extremely hygroscopic and will not readily crystallize Its freebase form although less stable than DMT hemifumarate is favored by recreational users choosing to vaporize the chemical as it has a lower boiling point 105 Biosynthesis edit nbsp Biosynthetic pathway for N N dimethyltryptamineDimethyltryptamine is an indole alkaloid derived from the shikimate pathway Its biosynthesis is relatively simple and summarized in the adjacent picture In plants the parent amino acid L tryptophan is produced endogenously where in animals L tryptophan is an essential amino acid coming from diet No matter the source of L tryptophan the biosynthesis begins with its decarboxylation by an aromatic amino acid decarboxylase AADC enzyme step 1 The resulting decarboxylated tryptophan analog is tryptamine Tryptamine then undergoes a transmethylation step 2 the enzyme indolethylamine N methyltransferase INMT catalyzes the transfer of a methyl group from cofactor S adenosylmethionine SAM via nucleophilic attack to tryptamine This reaction transforms SAM into S adenosylhomocysteine SAH and gives the intermediate product N methyltryptamine NMT 107 108 NMT is in turn transmethylated by the same process step 3 to form the end product N N dimethyltryptamine Tryptamine transmethylation is regulated by two products of the reaction SAH 109 110 111 and DMT 109 111 were shown ex vivo to be among the most potent inhibitors of rabbit INMT activity This transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of SAM methyl group with carbon 14 14C CH3 SAM 107 109 111 112 113 Laboratory synthesis edit DMT can be synthesized through several possible pathways from different starting materials The two most commonly encountered synthetic routes are through the reaction of indole with oxalyl chloride followed by reaction with dimethylamine and reduction of the carbonyl functionalities with lithium aluminium hydride to form DMT 114 The second commonly encountered route is through the N N dimethylation of tryptamine using formaldehyde followed by reduction with sodium cyanoborohydride or sodium triacetoxyborohydride Sodium borohydride can be used but requires a larger excess of reagents and lower temperatures due to it having a higher selectivity for carbonyl groups as opposed to imines 115 Procedures using sodium cyanoborohydride and sodium triacetoxyborohydride presumably created in situ from cyanoborohydride though this may not be the case due to the presence of water or methanol also result in the creation of cyanated tryptamine and beta carboline byproducts of unknown toxicity while using sodium borohydride in absence of acid does not 116 Bufotenine a plant extract can also be synthesized into DMT 117 Alternatively an excess of methyl iodide or methyl p toluenesulfonate and sodium carbonate can be used to over methylate tryptamine resulting in the creation of a quaternary ammonium salt which is then dequaternized demethylated in ethanolamine to yield DMT The same two step procedure is used to synthesize other N N dimethylated compounds such as 5 MeO DMT 118 Clandestine manufacture edit nbsp DMT during various stages of purificationIn a clandestine setting DMT is not typically synthesized due to the lack of availability of the starting materials namely tryptamine and oxalyl chloride Instead it is more often extracted from plant sources using a nonpolar hydrocarbon solvent such as naphtha or heptane and a base such as sodium hydroxide citation needed Alternatively an acid base extraction is sometimes used instead A variety of plants contain DMT at sufficient levels for being viable sources 4 but specific plants such as Mimosa tenuiflora Acacia acuminata and Acacia confusa are most often used The chemicals involved in the extraction are commonly available The plant material may be illegal to procure in some countries The end product DMT is illegal in most countries Evidence in mammals edit Published in Science in 1961 Julius Axelrod found an N methyltransferase enzyme capable of mediating biotransformation of tryptamine into DMT in a rabbit s lung 107 This finding initiated a still ongoing scientific interest in endogenous DMT production in humans and other mammals 108 44 From then on two major complementary lines of evidence have been investigated localization and further characterization of the N methyltransferase enzyme and analytical studies looking for endogenously produced DMT in body fluids and tissues 108 In 2013 researchers reported DMT in the pineal gland microdialysate of rodents 119 A study published in 2014 reported the biosynthesis of N N dimethyltryptamine DMT in the human melanoma cell line SK Mel 147 including details on its metabolism by peroxidases 120 It is assumed that more than half of the amount of DMT produced by the acidophilic cells of the pineal gland is secreted before and during death citation needed the amount being 2 5 3 4 mg kg However this claim by Strassman has been criticized by David Nichols who notes that DMT does not appear to be produced in any meaningful amount by the pineal gland Removal or calcification of the pineal gland does not induce any of the symptoms caused by removal of DMT The symptoms presented are consistent solely with reduction in melatonin which is the pineal gland s known function Nichols instead suggests that dynorphin and other endorphins are responsible for the reported euphoria experienced by patients during a near death experience 121 In 2014 researchers demonstrated the immunomodulatory potential of DMT and 5 MeO DMT through the Sigma 1 receptor of human immune cells This immunomodulatory activity may contribute to significant anti inflammatory effects and tissue regeneration 122 Endogenous DMT edit N N Dimethyltryptamine DMT a psychedelic compound identified endogenously in mammals is biosynthesized by aromatic L amino acid decarboxylase AADC and indolethylamine N methyltransferase INMT Studies have investigated brain expression of INMT transcript in rats and humans coexpression of INMT and AADC mRNA in rat brain and periphery and brain concentrations of DMT in rats INMT transcripts were identified in the cerebral cortex pineal gland and choroid plexus of both rats and humans via in situ hybridization Notably INMT mRNA was colocalized with AADC transcript in rat brain tissues in contrast to rat peripheral tissues where there existed little overlapping expression of INMT with AADC transcripts Additionally extracellular concentrations of DMT in the cerebral cortex of normal behaving rats with or without the pineal gland were similar to those of canonical monoamine neurotransmitters including serotonin A significant increase of DMT levels in the rat visual cortex was observed following induction of experimental cardiac arrest a finding independent of an intact pineal gland These results show for the first time that the rat brain is capable of synthesizing and releasing DMT at concentrations comparable to known monoamine neurotransmitters and raise the possibility that this phenomenon may occur similarly in human brains 123 The first claimed detection of mammalian endogenous DMT was published in June 1965 German researchers F Franzen and H Gross report to have evidenced and quantified DMT along with its structural analog bufotenin 5 HO DMT in human blood and urine 124 In an article published four months later the method used in their study was strongly criticized and the credibility of their results challenged 125 Few of the analytical methods used prior to 2001 to measure levels of endogenously formed DMT had enough sensitivity and selectivity to produce reliable results 126 127 Gas chromatography preferably coupled to mass spectrometry GC MS is considered a minimum requirement 127 A study published in 2005 44 implements the most sensitive and selective method ever used to measure endogenous DMT 128 liquid chromatography tandem mass spectrometry with electrospray ionization LC ESI MS MS allows for reaching limits of detection LODs 12 to 200 fold lower than those attained by the best methods employed in the 1970s The data summarized in the table below are from studies conforming to the abovementioned requirements abbreviations used CSF cerebrospinal fluid LOD limit of detection n number of samples ng L and ng kg nanograms 10 9 g per litre and nanograms per kilogram respectively DMT in body fluids and tissues NB units have been harmonized Species Sample ResultsHuman Blood serum lt LOD n 66 44 Blood plasma lt LOD n 71 44 lt LOD n 38 1 000 amp 10 600 ng L n 2 129 Whole blood lt LOD n 20 50 790 ng L n 20 130 Urine lt 100 ng L n 9 44 lt LOD n 60 160 540 ng L n 5 127 Detected in n 10 by GC MS 131 Feces lt 50 ng kg n 12 130 ng kg n 1 44 Kidney 15 ng kg n 1 44 Lung 14 ng kg n 1 44 Lumbar CSF 100 370 ng L n 1 2 330 7 210 ng L n 3 350 amp 850 ng L n 2 45 Rat Kidney 12 amp 16 ng kg n 2 44 Lung 22 amp 12 ng kg n 2 44 Liver 6 amp 10 ng kg n 2 44 Brain 10 amp 15 ng kg n 2 44 Measured in synaptic vesicular fraction 46 Rabbit Liver lt 10 ng kg n 1 44 A 2013 study found DMT in microdialysate obtained from a rat s pineal gland providing evidence of endogenous DMT in the mammalian brain 119 In 2019 experiments showed that the rat brain is capable of synthesizing and releasing DMT These results raise the possibility that this phenomenon may occur similarly in human brains 48 Detection in body fluids edit DMT may be measured in blood plasma or urine using chromatographic techniques as a diagnostic tool in clinical poisoning situations or to aid in the medicolegal investigation of suspicious deaths In general blood or plasma DMT levels in recreational users of the drug are in the 10 30 mg L range during the first several hours post ingestion citation needed Less than 0 1 of an oral dose is eliminated unchanged in the 24 hour urine of humans 132 133 clarification needed INMT edit Before techniques of molecular biology were used to localize indolethylamine N methyltransferase INMT 111 113 characterization and localization went on a par samples of the biological material where INMT is hypothesized to be active are subject to enzyme assay Those enzyme assays are performed either with a radiolabeled methyl donor like 14C CH3 SAM to which known amounts of unlabeled substrates like tryptamine are added 108 or with addition of a radiolabeled substrate like 14C NMT to demonstrate in vivo formation 109 112 As qualitative determination of the radioactively tagged product of the enzymatic reaction is sufficient to characterize INMT existence and activity or lack of analytical methods used in INMT assays are not required to be as sensitive as those needed to directly detect and quantify the minute amounts of endogenously formed DMT The essentially qualitative method thin layer chromatography TLC was thus used in a vast majority of studies 108 Also robust evidence that INMT can catalyze transmethylation of tryptamine into NMT and DMT could be provided with reverse isotope dilution analysis coupled to mass spectrometry for rabbit 134 135 and human 136 lung during the early 1970s Selectivity rather than sensitivity proved to be a challenge for some TLC methods with the discovery in 1974 1975 that incubating rat blood cells or brain tissue with 14C CH3 SAM and NMT as substrate mostly yields tetrahydro b carboline derivatives 108 109 137 and negligible amounts of DMT in brain tissue 108 It is indeed simultaneously realized that the TLC methods used thus far in almost all published studies on INMT and DMT biosynthesis are incapable to resolve DMT from those tetrahydro b carbolines 108 These findings are a blow for all previous claims of evidence of INMT activity and DMT biosynthesis in avian 138 and mammalian brain 139 140 including in vivo 141 142 as they all relied upon use of the problematic TLC methods 108 their validity is doubted in replication studies that make use of improved TLC methods and fail to evidence DMT producing INMT activity in rat and human brain tissues 143 144 Published in 1978 the last study attempting to evidence in vivo INMT activity and DMT production in brain rat with TLC methods finds biotransformation of radiolabeled tryptamine into DMT to be real but insignificant 145 Capability of the method used in this latter study to resolve DMT from tetrahydro b carbolines is questioned later 109 To localize INMT a qualitative leap is accomplished with use of modern techniques of molecular biology and of immunohistochemistry In humans a gene encoding INMT is determined to be located on chromosome 7 113 Northern blot analyses reveal INMT messenger RNA mRNA to be highly expressed in rabbit lung 111 and in human thyroid adrenal gland and lung 113 146 Intermediate levels of expression are found in human heart skeletal muscle trachea stomach small intestine pancreas testis prostate placenta lymph node and spinal cord 113 146 Low to very low levels of expression are noted in rabbit brain 113 and human thymus liver spleen kidney colon ovary and bone marrow 113 146 INMT mRNA expression is absent in human peripheral blood leukocytes whole brain and in tissue from 7 specific brain regions thalamus subthalamic nucleus caudate nucleus hippocampus amygdala substantia nigra and corpus callosum 113 146 Immunohistochemistry showed INMT to be present in large amounts in glandular epithelial cells of small and large intestines In 2011 immunohistochemistry revealed the presence of INMT in primate nervous tissue including retina spinal cord motor neurons and pineal gland 49 A 2020 study using in situ hybridization a far more accurate tool than the northern blot analysis found mRNA coding for INMT expressed in the human cerebral cortex choroid plexus and pineal gland 48 Pharmacology editPharmacokinetics edit DMT peak level concentrations Cmax measured in whole blood after intramuscular IM injection 0 7 mg kg n 11 147 and in plasma following intravenous IV administration 0 4 mg kg n 10 21 of fully psychedelic doses are in the range of around 14 to 154 mg L and 32 to 204 mg L respectively The corresponding molar concentrations of DMT are therefore in the range of 0 074 0 818 mmol L in whole blood and 0 170 1 08 mmol in plasma However several studies have described active transport and accumulation of DMT into rat and dog brains following peripheral administration 148 149 150 151 152 Similar active transport and accumulation processes likely occur in human brains and may concentrate DMT in brain by several fold or more relatively to blood resulting in local concentrations in the micromolar or higher range Such concentrations would be commensurate with serotonin brain tissue concentrations which have been consistently determined to be in the 1 5 4 mmol L range 153 154 Closely coextending with peak psychedelic effects mean time to reach peak concentrations Tmax was determined to be 10 15 minutes in whole blood after IM injection 147 and 2 minutes in plasma after IV administration 21 When taken orally mixed in an ayahuasca decoction and in freeze dried ayahuasca gel caps DMT Tmax is considerably delayed 107 59 32 5 minutes 155 and 90 120 minutes 156 respectively The pharmacokinetics for vaporizing DMT have not been studied or reported Neurogenesis edit See also 5 MeO DMT Neurogenesis Ayahuasca Neurogenesis and Banisteriopsis caapi Neurogenesis In September 2020 an in vitro and in vivo study showed that DMT present in the ayahuasca infusion promotes neurogenesis 157 Pharmacodynamics edit DMT binds non selectively with affinities below 0 6 mmol L to the following serotonin receptors 5 HT1A 158 159 160 5 HT1B 158 161 5 HT1D 158 160 161 5 HT2A 158 160 161 162 5 HT2B 158 161 5 HT2C 158 161 162 5 HT6 158 161 and 5 HT7 158 161 An agonist action has been determined at 5 HT1A 159 5 HT2A and 5 HT2C 158 161 162 Its efficacies at other serotonin receptors remain to be determined Of special interest will be the determination of its efficacy at human 5 HT2B receptor as two in vitro assays evidenced DMT s high affinity for this receptor 0 108 µmol L 161 and 0 184 µmol L 158 This may be of importance because chronic or frequent uses of serotonergic drugs showing preferential high affinity and clear agonism at 5 HT2B receptor have been causally linked to valvular heart disease 163 164 165 It has also been shown to possess affinity for the dopamine D1 a1 adrenergic a2 adrenergic imidazoline 1 and s1 receptors 160 161 166 Converging lines of evidence established activation of the s1 receptor at concentrations of 50 100 mmol L 167 Its efficacies at the other receptor binding sites are unclear It has also been shown in vitro to be a substrate for the cell surface serotonin transporter SERT expressed in human platelets and the rat vesicular monoamine transporter 2 VMAT2 which was transiently expressed in fall armyworm Sf9 cells DMT inhibited SERT mediated serotonin uptake into platelets at an average concentration of 4 00 0 70 µmol L and VMAT2 mediated serotonin uptake at an average concentration of 93 6 8 µmol L 168 As with other so called classical hallucinogens 169 a large part of DMT psychedelic effects can be attributed to a functionally selective activation of the 5 HT2A receptor 21 158 170 171 172 173 174 DMT concentrations eliciting 50 of its maximal effect half maximal effective concentration EC50 at the human 5 HT2A receptor in vitro are in the 0 118 0 983 µmol L range 158 161 162 175 This range of values coincides well with the range of concentrations measured in blood and plasma after administration of a fully psychedelic dose see Pharmacokinetics As DMT has been shown to have slightly better efficacy EC50 at human serotonin 2C receptor than at the 2A receptor 161 162 5 HT2C is also likely implicated in DMT s overall effects 171 176 Other receptors such as 5 HT1A 160 171 173 and s1 167 177 may also play a role In 2009 it was hypothesized that DMT may be an endogenous ligand for the s1 receptor 167 177 The concentration of DMT needed for s1 activation in vitro 50 100 µmol L is similar to the behaviorally active concentration measured in mouse brain of approximately 106 µmol L 178 This is minimally 4 orders of magnitude higher than the average concentrations measured in rat brain tissue or human plasma under basal conditions see Endogenous DMT so s1 receptors are likely to be activated only under conditions of high local DMT concentrations If DMT is stored in synaptic vesicles 168 such concentrations might occur during vesicular release To illustrate while the average concentration of serotonin in brain tissue is in the 1 5 4 µmol L range 153 154 the concentration of serotonin in synaptic vesicles was measured at 270 mM 179 Following vesicular release the resulting concentration of serotonin in the synaptic cleft to which serotonin receptors are exposed is estimated to be about 300 µmol L Thus while in vitro receptor binding affinities efficacies and average concentrations in tissue or plasma are useful they are not likely to predict DMT concentrations in the vesicles or at synaptic or intracellular receptors Under these conditions notions of receptor selectivity are moot and it seems probable that most of the receptors identified as targets for DMT see above participate in producing its psychedelic effects Binding sites Binding affinity Ki mM 180 5 HT1A 0 0755 HT2A 0 2375 HT2C 0 424D1 6D2 3D3 6 3a1A 1 3a2A 2 1TAAR1 2 2H1 0 22SERT 6DAT 22NET 6 5Society and culture editBlack market edit Electronic cigarette cartridges filled with DMT started to be sold on the black market in 2018 181 See also editDimethyltryptamine N oxide Psychedelic drug List of psychoactive plants MPMI Serotonergic psychedelic Psychoplastogen Alexander Shulgin SN 22 Rick StrassmanReferences edit Anvisa 2023 07 24 RDC Nº 804 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 804 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 2023 07 25 Archived from the original on 2023 08 27 Retrieved 2023 08 27 Hafelinger G Nimtz M Horstmann V Benz T 1999 Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien Synthesen Spektroskopie sowie analytische Trennungen mittels Kapillar GC Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents synthesis spectroscopic characterizations and separations by capillary gas chromatography Zeitschrift fur Naturforschung B 54 3 397 414 doi 10 1515 znb 1999 0319 S2CID 101000504 Corothie E Nakano T May 1969 Constituents of the bark of Virola sebifera Planta Medica 17 2 184 188 doi 10 1055 s 0028 1099844 PMID 5792479 S2CID 43312376 a b Carbonaro TM Gatch MB September 2016 Neuropharmacology of N N dimethyltryptamine Brain Research Bulletin 126 Pt 1 74 88 doi 10 1016 j brainresbull 2016 04 016 PMC 5048497 PMID 27126737 a b c d e f McKenna DJ Towers GH Abbott F April 1984 Monoamine oxidase inhibitors in South American hallucinogenic plants tryptamine and beta carboline constituents of ayahuasca Journal of Ethnopharmacology 10 2 195 223 doi 10 1016 0378 8741 84 90003 5 PMID 6587171 Haroz R Greenberg MI November 2005 Emerging drugs of abuse The Medical Clinics of North America 89 6 1259 1276 doi 10 1016 j mcna 2005 06 008 OCLC 610327022 PMID 16227062 a b Pickover C 2005 Sex Drugs Einstein and Elves Sushi Psychedelics Parallel Universes and the Quest for Transcendence Smart Publications ISBN 978 1 890572 17 4 a b Erowid DMT Dimethyltryptamine Vault Erowid org Retrieved 20 September 2012 a b c Torres CM Repke DB 2006 Anadenanthera Visionary Plant Of Ancient South America Binghamton NY Haworth Herbal pp 107 122 ISBN 978 0 7890 2642 2 Rivier L Lindgren JE 1972 Ayahuasca the South American hallucinogenic drink An ethnobotanical and chemical investigation Economic Botany 26 2 101 129 doi 10 1007 BF02860772 ISSN 0013 0001 S2CID 34669901 Ott J 2001 Pharmanopo psychonautics human intranasal sublingual intrarectal pulmonary and oral pharmacology of bufotenine PDF Journal of Psychoactive Drugs 33 3 273 281 doi 10 1080 02791072 2001 10400574 PMID 11718320 S2CID 5877023 a b c d Strassman RJ 2001 DMT The Spirit Molecule A Doctor s Revolutionary Research into the Biology of Near Death and Mystical Experiences Rochester VT Park Street ISBN 978 0 89281 927 0 Chapter summaries Retrieved 27 February 2012 Szabo I Varga VE Dvoracsko S Farkas AE Kormoczi T Berkecz R et al July 2021 N N Dimethyltryptamine attenuates spreading depolarization and restrains neurodegeneration by sigma 1 receptor activation in the ischemic rat brain Neuropharmacology 192 108612 doi 10 1016 j neuropharm 2021 108612 PMID 34023338 S2CID 235169696 Pinto V 30 July 2021 Akome Developing Psychedelic Parkinson s Therapy Seeks US Patent Retrieved 2022 09 11 Clinical trial number NCT04673383 for A Double blind Randomised Placebo controlled Study of Intravenous Doses of SPL026 DMT Fumarate a Serotonergic Psychedelic in Healthy Subjects Part A and Patients With Major Depressive Disorder Part B at ClinicalTrials gov Clinical trial number NCT05553691 for An Open Label Study Investigating the Safety Tolerability Pharmacokinetics Pharmacodynamics amp Exploratory Efficacy of Intravenous SPL026 Drug Product DMT Fumarate Alone or in Combination With SSRIs in Patients With Major Depressive Disorder at ClinicalTrials gov Ly C Greb AC Cameron LP Wong JM Barragan EV Wilson PC et al June 2018 Psychedelics Promote Structural and Functional Neural Plasticity Cell Reports 23 11 3170 3182 doi 10 1016 j celrep 2018 05 022 PMC 6082376 PMID 29898390 Corbett L Christian ST Morin RD Benington F Smythies JR February 1978 Hallucinogenic N methylated indolealkylamines in the cerebrospinal fluid of psychiatric and control populations The British Journal of Psychiatry 132 2 139 144 doi 10 1192 bjp 132 2 139 PMID 272218 S2CID 37144421 a b Strassman RJ Qualls CR Uhlenhuth EH Kellner R February 1994 Dose response study of N N dimethyltryptamine in humans II Subjective effects and preliminary results of a new rating scale Archives of General Psychiatry 51 2 98 108 doi 10 1001 archpsyc 1994 03950020022002 PMID 8297217 Gomez Emilsson A 5 October 2019 The Hyperbolic Geometry of DMT Experiences Speech Harvard Science of Psychedelics Club Harvard University Cambridge Massachusetts Qualia Research Institute Archived from the original on 2021 12 11 Retrieved 27 April 2020 a b c d e f g h i Strassman RJ Qualls CR February 1994 Dose response study of N N dimethyltryptamine in humans I Neuroendocrine autonomic and cardiovascular effects Archives of General Psychiatry 51 2 85 97 doi 10 1001 archpsyc 1994 03950020009001 PMID 8297216 DMT How and Why to Get Off users aalto fi Archived from the original on 2021 01 26 Retrieved 2021 03 24 St John G 2018 The Breakthrough Experience DMT Hyperspace and its Liminal Aesthetics Anthropology of Consciousness 29 1 57 76 doi 10 1111 anoc 12089 ISSN 1556 3537 DMT Erowid Exp Break Through erowid org Retrieved 2021 03 24 a b Lamparter D Dittrich A 1995 Intraindividuelle Stabilitat von ABZ unter sensorischer Deprivation N N Dimethyltryptamin DMT und Stickoxydul Yearbook of the European College for the Study of Consciousness 33 44 Vollenweider FX December 2001 Brain mechanisms of hallucinogens and entactogens Dialogues in Clinical Neuroscience 3 4 265 279 doi 10 31887 DCNS 2001 3 4 fxvollenweider PMC 3181663 PMID 22033605 Strassman R 2001 Dmt the Spirit Molecule A Doctor s Revolutionary Research into the Biology of near Death and Mystical Experiences pp 187 188 also pp 173 174 ISBN 978 0 89281 927 0 I had expected to hear about some of these types of experiences once we began giving DMT I was familiar with Terence McKenna s tales of the self transforming machine elves he encountered after smoking high doses of the drug Interviews conducted with twenty experienced DMT smokers before beginning the New Mexico research also yielded some tales of similar meetings with such entities Since most of these people were from California I admittedly chalked up these stories to some kind of West Coast eccentricity McKenna T 1975 The Invisible Landscape Mind Hallucinogens and the I Ching Graham St John 2015 Mystery School in Hyperspace A Cultural History of DMT North Atlantic Books Evolver ISBN 978 1 58394 732 6 Berkeley CA chapters 4 8 and 12 a b c Strassman R 2014 DMT and the Soul of Prophecy A New Science of Spiritual Revelation in the Hebrew Bible Simon and Schuster ISBN 978 1 62055 168 4 Interview Dr Rick Strassman AVI SOLOMON 6 39 AM TUE 3 May 2011 Strassman R 2001 DMT the Spirit Molecule A Doctor s Revolutionary Research into the Biology of Near Death and Mystical Experiences pp 206 208 ISBN 978 0 89281 927 0 Strassman R 2001 DMT the Spirit Molecule A Doctor s Revolutionary Research into the Biology of near Death and Mystical Experiences pp 202 ISBN 978 0 89281 927 0 Hanks MA 10 September 2010 Causal Multiplicity The Science Behind Schizophrenia Gallimore AR Luke DP 15 December 2015 DMT research from 1956 to the edge of time PDF Archived PDF from the original on 2016 03 24 a b Gallimore A 2013 Evolutionary Implications of the Astonishing Psychoactive Effects of N N Dimethyltryptamine DMT Journal of Scientific Exploration 27 3 455 503 unreliable source New study offers a detailed glimpse into the otherworldly encounters produced by the psychedelic drug 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DOM Mal nr meddelad i Stockholm den 13 December 2018 PDF Domstol se Archived PDF from the original on 2020 03 09 Retrieved 8 March 2022 Wetgeving rond LSD en tripmiddelen Druglijn be O Brien C 8 May 2019 Health Canada allows more religious groups to import psychedelic ayahuasca Ctvnews ca Retrieved 8 March 2022 Rochester J 17 July 2017 How Our Santo Daime Church Received Religious Exemption to Use Ayahuasca in Canada Chacruna net Retrieved 1 May 2019 Church of the Holy Light of the Queen v Mukasey PDF Archived from the original PDF on 3 October 2011 Retrieved 5 December 2018 Church of the Holy Light of the Queen v Mukasey D Ore 2009 permanently enjoins Defendants from prohibiting or penalizing the sacramental use of Daime tea by Plaintiffs during Plaintiffs religious ceremonies Text Berry M NZPA 19 May 2011 Rare drug bound for Blenheim Marlborough Express Blenheim New Zealand Fairfax New Zealand Retrieved 23 May 2012 Schedule 1 Class A controlled drugs Misuse of Drugs Act 1975 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classic hallucinogens PDF European Neuropsychopharmacology 26 8 1327 1337 doi 10 1016 j euroneuro 2016 05 001 PMID 27216487 S2CID 6685927 Black L New on the Black Market Vape Pens Full of DMT The Stranger External links edit nbsp Wikimedia Commons has media related to Dimethyltryptamine DMT chapter from TiHKAL Retrieved from https en wikipedia org w index php title N N Dimethyltryptamine amp oldid 1207897568, wikipedia, wiki, book, books, library,

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