Trimethoxyamphetamines (TMAs) are a family of isomericpsychedelichallucinogenicdrugs. There exist six different TMAs that differ only in the position of the three methoxygroups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylaminecactusalkaloidmescaline. The TMAs are substituted amphetamines, however, their mechanism of action is more complex than that of the unsubstituted compound amphetamine, probably involving agonist activity on serotonin receptors such as the 5HT2A receptor in addition to the generalised dopamine receptor agonism typical of most amphetamines. This action on serotonergic receptors likely underlie the psychedelic effects of these compounds. It is reported that some TMAs elicit a range of emotions ranging from sadness to empathy and euphoria.[citation needed] TMA was first synthesized by Hey, in 1947.[1] Synthesis data as well as human activity data has been published in the book PiHKAL.
The most important TMA compound from a pharmacological standpoint is TMA-2, as this isomer has been much more widely used as a recreational drug and sold on the grey market as a so-called research chemical; TMA (sometimes referred to as "mescalamphetamine" or TMA-1) and TMA-6 have also been used in this way to a lesser extent. These three isomers are significantly more active as hallucinogenic drugs, and have consequently been placed onto the illegal drug schedules in some countries such as the Netherlands and Japan. The other three isomers TMA-3, TMA-4, and TMA-5 are not known to have been used as recreational drugs to any great extent.
Note: Because they are isomers, the TMAs have the same chemical formula, C12H19NO3, and the same molecular mass, 225.28 g/mol.
Properties
Compound
Pattern
Dose
Duration
TMA
3,4,5
100 – 250 mg
6 - 8 h
TMA-2
2,4,5
20 – 40 mg
8 - 12 h
TMA-3
2,3,4
> 100 mg
unknown
TMA-4
2,3,5
> 80 mg
~ 6 h
TMA-5
2,3,6
≥ 30 mg
8 - 10 h
TMA-6
2,4,6
25 – 50 mg
12 - 16 h
Legality
Sweden
Sveriges riksdag added TMA-2 to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Dec 30, 1999, published by Medical Products Agency in their regulation LVFS 2004:3 listed as 2,4,5-trimetoxiamfetamin (TMA-2).[2]
EMCDDA Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs
January 07, 2023
trimethoxyamphetamine, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news, newspapers, books, scholar, jstor, june. This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Trimethoxyamphetamine news newspapers books scholar JSTOR June 2013 Learn how and when to remove this template message Trimethoxyamphetamines TMAs are a family of isomeric psychedelic hallucinogenic drugs There exist six different TMAs that differ only in the position of the three methoxy groups TMA TMA 2 TMA 3 TMA 4 TMA 5 and TMA 6 The TMAs are analogs of the phenethylamine cactus alkaloid mescaline The TMAs are substituted amphetamines however their mechanism of action is more complex than that of the unsubstituted compound amphetamine probably involving agonist activity on serotonin receptors such as the 5HT2A receptor in addition to the generalised dopamine receptor agonism typical of most amphetamines This action on serotonergic receptors likely underlie the psychedelic effects of these compounds It is reported that some TMAs elicit a range of emotions ranging from sadness to empathy and euphoria citation needed TMA was first synthesized by Hey in 1947 1 Synthesis data as well as human activity data has been published in the book PiHKAL The most important TMA compound from a pharmacological standpoint is TMA 2 as this isomer has been much more widely used as a recreational drug and sold on the grey market as a so called research chemical TMA sometimes referred to as mescalamphetamine or TMA 1 and TMA 6 have also been used in this way to a lesser extent These three isomers are significantly more active as hallucinogenic drugs and have consequently been placed onto the illegal drug schedules in some countries such as the Netherlands and Japan The other three isomers TMA 3 TMA 4 and TMA 5 are not known to have been used as recreational drugs to any great extent Contents 1 TMAs 2 Properties 3 Legality 3 1 Sweden 4 See also 5 References 6 External linksTMAs EditTMAChemical name 1 3 4 5 Trimethoxyphenyl propan 2 amine 3 4 5 trimethoxyamphetamineMelting point 220 221 C hydrochloride SMILES NC C CC1 CC OC C OC C OC C1CAS number1082 88 8 UNII Ref Y UNII P2K02L3YON TMA 2Chemical name 1 2 4 5 Trimethoxyphenyl propan 2 amine 2 4 5 trimethoxyamphetamineMelting point 188 5 189 5 C hydrochloride SMILES NC C CC1 C OC C C OC C OC C1CAS number1083 09 6 UNII Ref Y UNII 713Z3SL0TJ TMA 3Chemical name 1 2 3 4 Trimethoxyphenyl propan 2 amine 2 3 4 trimethoxyamphetamineMelting point 148 149 C hydrochloride SMILES NC C CC1 CC C OC C OC C1OCCAS number1082 23 1 UNII Ref Y UNII 9T3SO4A6HM TMA 4Chemical name 1 2 3 5 Trimethoxyphenyl propan 2 amine 2 3 5 trimethoxyamphetamineMelting point 118 119 C hydrochloride SMILES NC C CC1 CC OC CC OC C1OCCAS number23693 14 3 UNII Ref Y UNII LEL94CV318 TMA 5Chemical name 1 2 3 6 Trimethoxyphenyl propan 2 amine 2 3 6 trimethoxyamphetamineMelting point 124 125 C hydrochloride SMILES NC C CC1 C OC C CC OC C1OCCAS number20513 16 0 UNII Ref Y UNII E0NJ557A3E TMA 6Chemical name 1 2 4 6 Trimethoxyphenyl propan 2 amine 2 4 6 trimethoxyamphetamineMelting point 207 208 C hydrochloride SMILES NC C CC1 C OC C C OC C C1OCCAS number15402 79 6 UNII Ref Y UNII 2X84DCO6GA Note Because they are isomers the TMAs have the same chemical formula C12H19NO3 and the same molecular mass 225 28 g mol Properties EditCompound Pattern Dose DurationTMA 3 4 5 100 250 mg 6 8 hTMA 2 2 4 5 20 40 mg 8 12 hTMA 3 2 3 4 gt 100 mg unknownTMA 4 2 3 5 gt 80 mg 6 hTMA 5 2 3 6 30 mg 8 10 hTMA 6 2 4 6 25 50 mg 12 16 hLegality EditSweden Edit Sveriges riksdag added TMA 2 to schedule I substances plant materials and fungi which normally do not have medical use as narcotics in Sweden as of Dec 30 1999 published by Medical Products Agency in their regulation LVFS 2004 3 listed as 2 4 5 trimetoxiamfetamin TMA 2 2 See also EditMescaline Hallucinogenic drug AmphetamineReferences Edit Hey P 1947 The synthesis of a new homologue of mescaline Quart J Pharm Pharmacol 20 129 http www lakemedelsverket se upload lvfs LVFS 2004 3 pdf bare URL PDF External links EditPiHKAL entries TMA TMA in PiHKAL info TMA 2 TMA 2 in PiHKAL info TMA 3 TMA 3 in PiHKAL info TMA 4 TMA 4 in PiHKAL info TMA 5 TMA 5 in PiHKAL info TMA 6 TMA 6 in PiHKAL info Erowid TMA vault EMCDDA Report on the risk assessment of TMA 2 in the framework of the joint action on new synthetic drugs Retrieved from https en wikipedia org w index php title Trimethoxyamphetamine amp oldid 1117752646, wikipedia, wiki, book, books, library,
