STP was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.[2]
In mid-1967, tablets containing 20 mg (later 10 mg) of STP were widely distributed in the Haight-Ashbury District of San Francisco under the name of STP, having been manufactured by underground chemists Owsley Stanley and Tim Scully. This short-lived appearance of STP on the black market proved disastrous for several reasons. First, the tablets contained an excessively high dose of the chemical. This, combined with DOM's slow onset of action (which encouraged some users, familiar with drugs that have quicker onsets, such as LSD, to re-dose) and its remarkably long duration, caused many users to panic and sent some to the emergency room. Second, treatment of such overdoses was complicated by the fact that no one at the time knew that the tablets called STP were, in fact, DOM.
EffectsEdit
Effects of this drug include substantial perceptual changes such as blurred vision, multiple images, vibration of objects, visual alterations, distorted shapes, enhancement of details, slowed passage of time, increased sexual drive and pleasure, and increased contrasts. It may cause mystical experiences and changes in consciousness. It may also cause pupillary dilation and a rise in systolic blood pressure.[3]
PharmacologyEdit
DOM is a selective 5-HT2A, 5-HT2B, and 5-HT2C receptorpartial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOM is often used in scientific research when studying the 5-HT2 receptor subfamily. DOM is a chiral molecule, and R-(−)-DOM is the more active enantiomer, functioning as a potent agonist of the serotonin 5-HT family of receptors; mainly of the 5-HT2 subtype.[4]
Analogues and derivativesEdit
Chemical structures of some DOM variants
The 2,6-dimethoxy positional isomer of DOM, known as Ψ-DOM, is also mentioned in PiHKAL as being active, as is the alpha-ethyl homologue Ariadne. Analogues where the methoxy groups at the 2,5- positions of the aromatic ring have been altered have also been synthesised and tested as part of an effort to identify the binding mode of DOM at the 5-HT2A receptor. Both the 2- and 5- O-desmethyl derivatives 2-DM-DOM and 5-DM-DOM, and the 2- and 5- ethyl analogues 2-Et-DOM and 5-Et-DOM have been tested, but in all cases were significantly less potent than the corresponding methoxy compound, showing the importance of the oxygen lone pairs in 5-HT2A binding.[5][6]
ToxicityEdit
Very little is known about the toxicity of DOM. According to Alexander Shulgin, the effects of DOM typically last 14 to 20 hours, though other clinical trials indicate a duration of 7 to 8 hours.[3]
Legal statusEdit
CanadaEdit
Listed as a Schedule 1, as it is an analogue of amphetamine.
United StatesEdit
DOM is Schedule I in the United States. This means it is illegal to manufacture, buy, possess, or distribute (make, trade, own or give) without a DEA license.
AustraliaEdit
DOM is schedule 9 under the Australia Poisons standard.[7] A schedule 9 substance is a "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 Commonwealth and/or State or Territory Health Authorities."[7]
^(PDF) (23rd ed.). International Narcotics Control Board. August 2003. p. 4. Archived from the original (PDF) on 19 December 2013. Retrieved 22 February 2014.
^Shulgin, Alexander (1991). Pihkal : a chemical love story. Berkeley, CA: Transform Press. pp. 53–56. ISBN978-0-9630096-0-9.
^ abSnyder, Solomon H.; Louis Faillace & Leo Hollister (3 November 1967). "2,5-Dimethoxy-4-methyl-amphetamine (STP): A New Hallucinogenic Drug" (PDF). Science. 158 (3801): 669–670. Bibcode:1967Sci...158..669S. doi:10.1126/science.158.3801.669. PMID 4860952. S2CID 24065654.
^Sanders-Bush, E; Burris, KD; Knoth, K (September 1988). "Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis". The Journal of Pharmacology and Experimental Therapeutics. 246 (3): 924–928. PMID 2843634.
^Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC (July 2003). "Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM". Pharmacology Biochemistry and Behavior. 75 (4): 845–52. doi:10.1016/S0091-3057(03)00159-X. PMID 12957227. S2CID 36463979.
^Braden, Michael Robert (May 2007). Towards a Biophysical Basis of Hallucinogen Action (Thesis). Purdue University. OCLC 703618147. Retrieved 28 February 2012.
dimethoxy, methylamphetamine, known, standing, serenity, tranquility, peace, psychedelic, substituted, amphetamine, first, synthesized, alexander, shulgin, later, reported, book, pihkal, chemical, love, story, classified, schedule, substance, united, states, s. 2 5 Dimethoxy 4 methylamphetamine DOM known as STP standing for Serenity Tranquility and Peace is a psychedelic and a substituted amphetamine It was first synthesized by Alexander Shulgin and later reported in his book PiHKAL A Chemical Love Story DOM is classified as a Schedule I substance in the United States and is similarly controlled in other parts of the world Internationally it is a Schedule I drug under the Convention on Psychotropic Substances 1 It is generally taken orally 2 5 Dimethoxy 4 methylamphetamine NamesPreferred IUPAC name 1 2 5 Dimethoxy 4 methylphenyl propan 2 amineOther names 2 5 Dimethoxy 4 methylamphetamineIdentifiersCAS Number 15588 95 1 Y43061 13 8 R Y43061 14 9 S Y3D model JSmol Interactive imageR isomer Interactive imageChEMBL ChEMBL317634 YChemSpider 9910656 YPubChem CID 11735949UNII UKI9MLD5OI YLX3MC6OB9X R Y0FRQ2JVN98 S YCompTox Dashboard EPA DTXSID50860611InChI InChI 1S C12H19NO2 c1 8 5 12 15 4 10 6 9 2 13 7 11 8 14 3 h5 7 9H 6 13H2 1 4H3 t9 m1 s1Key NTJQREUGJKIARY SECBINFHSA N YInChI 1 C12H19NO2 c1 8 5 12 15 4 10 6 9 2 13 7 11 8 14 3 h5 7 9H 6 13H2 1 4H3 t9 m1 s1Key NTJQREUGJKIARY SECBINFHBKSMILES O c1cc c OC cc1C C H N C C CR isomer N C H C CC1 C OC C C C C OC C1PropertiesChemical formula C 12H 19N O 2Molar mass 209 289 g mol 1Melting point 61 C 142 F 334 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 History 2 Effects 3 Pharmacology 3 1 Analogues and derivatives 4 Toxicity 5 Legal status 5 1 Canada 5 2 United States 5 3 Australia 5 4 United Kingdom 6 See also 7 References 8 External linksHistory EditSTP was first synthesized and tested in 1963 by Alexander Shulgin who was investigating the effect of 4 position substitutions on psychedelic amphetamines 2 In mid 1967 tablets containing 20 mg later 10 mg of STP were widely distributed in the Haight Ashbury District of San Francisco under the name of STP having been manufactured by underground chemists Owsley Stanley and Tim Scully This short lived appearance of STP on the black market proved disastrous for several reasons First the tablets contained an excessively high dose of the chemical This combined with DOM s slow onset of action which encouraged some users familiar with drugs that have quicker onsets such as LSD to re dose and its remarkably long duration caused many users to panic and sent some to the emergency room Second treatment of such overdoses was complicated by the fact that no one at the time knew that the tablets called STP were in fact DOM Effects EditEffects of this drug include substantial perceptual changes such as blurred vision multiple images vibration of objects visual alterations distorted shapes enhancement of details slowed passage of time increased sexual drive and pleasure and increased contrasts It may cause mystical experiences and changes in consciousness It may also cause pupillary dilation and a rise in systolic blood pressure 3 Pharmacology EditDOM is a selective 5 HT2A 5 HT2B and 5 HT2C receptor partial agonist Its psychedelic effects are mediated by its agonistic properties at the 5 HT2A receptor Due to its selectivity DOM is often used in scientific research when studying the 5 HT2 receptor subfamily DOM is a chiral molecule and R DOM is the more active enantiomer functioning as a potent agonist of the serotonin 5 HT family of receptors mainly of the 5 HT2 subtype 4 Analogues and derivatives Edit Chemical structures of some DOM variantsThe 2 6 dimethoxy positional isomer of DOM known as PS DOM is also mentioned in PiHKAL as being active as is the alpha ethyl homologue Ariadne Analogues where the methoxy groups at the 2 5 positions of the aromatic ring have been altered have also been synthesised and tested as part of an effort to identify the binding mode of DOM at the 5 HT2A receptor Both the 2 and 5 O desmethyl derivatives 2 DM DOM and 5 DM DOM and the 2 and 5 ethyl analogues 2 Et DOM and 5 Et DOM have been tested but in all cases were significantly less potent than the corresponding methoxy compound showing the importance of the oxygen lone pairs in 5 HT2A binding 5 6 Toxicity EditVery little is known about the toxicity of DOM According to Alexander Shulgin the effects of DOM typically last 14 to 20 hours though other clinical trials indicate a duration of 7 to 8 hours 3 Legal status EditCanada Edit Listed as a Schedule 1 as it is an analogue of amphetamine United States Edit DOM is Schedule I in the United States This means it is illegal to manufacture buy possess or distribute make trade own or give without a DEA license Australia Edit DOM is schedule 9 under the Australia Poisons standard 7 A schedule 9 substance is a 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 Commonwealth and or State or Territory Health Authorities 7 United Kingdom Edit DOM is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971 See also Edit2 5 Dimethoxy 4 Substituted AmphetaminesReferences Edit Green List List of Psychotropic Substances Under International Control PDF 23rd ed International Narcotics Control Board August 2003 p 4 Archived from the original PDF on 19 December 2013 Retrieved 22 February 2014 Shulgin Alexander 1991 Pihkal a chemical love story Berkeley CA Transform Press pp 53 56 ISBN 978 0 9630096 0 9 a b Snyder Solomon H Louis Faillace amp Leo Hollister 3 November 1967 2 5 Dimethoxy 4 methyl amphetamine STP A New Hallucinogenic Drug PDF Science 158 3801 669 670 Bibcode 1967Sci 158 669S doi 10 1126 science 158 3801 669 PMID 4860952 S2CID 24065654 Sanders Bush E Burris KD Knoth K September 1988 Lysergic acid diethylamide and 2 5 dimethoxy 4 methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis The Journal of Pharmacology and Experimental Therapeutics 246 3 924 928 PMID 2843634 Eckler JR Chang Fong J Rabin RA Smith C Teitler M Glennon RA Winter JC July 2003 Behavioral characterization of 2 O desmethyl and 5 O desmethyl metabolites of the phenylethylamine hallucinogen DOM Pharmacology Biochemistry and Behavior 75 4 845 52 doi 10 1016 S0091 3057 03 00159 X PMID 12957227 S2CID 36463979 Braden Michael Robert May 2007 Towards a Biophysical Basis of Hallucinogen Action Thesis Purdue University OCLC 703618147 Retrieved 28 February 2012 a b Poison Standard https www comlaw gov au Details F2015L01534 Html Text Toc420496379 Archived 2015 12 22 at the Wayback MachineExternal links EditDOM Entry in PiHKAL DOM Entry in PiHKAL info Erowid DOM Vault Retrieved from https en wikipedia org w index php title 2 5 Dimethoxy 4 methylamphetamine amp oldid 1104238622, wikipedia, wiki, book, books, library,
