Trimethoxyamphetamine

TMAs, also known as trimethoxyamphetamines, 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 action does not resemble that of the unsubstituted compound amphetamine, which is a stimulant and not a psychedelic. It is reported that some TMA's elicit a range of emotions ranging from sadness to empathy and euphoria. Several TMAs were first synthesized by the chemist Alexander Shulgin. Synthesis data as well as human activity data has been published in the book PiHKAL (Phenethylamines i Have Known And Loved).

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 black market and as a "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, and remain obscure scientific curiosities.

TMAs

TMA
Chemical name 1-(3,4,5-Trimethoxyphenyl)propan-2-amine,
3,4,5-trimethoxyamphetamine
Melting point 220 - 221 °C (hydrochloride)
SMILES NC(C)CC1=CC(OC)=C(OC)C(OC)=C1
CAS number
1082-88-8

TMA-2
Chemical name 1-(2,4,5-Trimethoxyphenyl)propan-2-amine,
2,4,5-trimethoxyamphetamine
Melting point 188.5 - 189.5 °C (hydrochloride)
SMILES NC(C)CC1=C(OC)C=C(OC)C(OC)=C1
CAS number
1083-09-6

TMA-3
Chemical name 1-(2,3,4-Trimethoxyphenyl)propan-2-amine,
2,3,4-trimethoxyamphetamine
Melting point 148 - 149 °C (hydrochloride)
SMILES NC(C)CC1=CC=C(OC)C(OC)=C1OC
CAS number
1082-23-1

TMA-4
Chemical name 1-(2,3,5-Trimethoxyphenyl)propan-2-amine,
2,3,5-trimethoxyamphetamine
Melting point 118 - 119 °C (hydrochloride)
SMILES NC(C)CC1=CC(OC)=CC(OC)=C1OC
CAS number
23693-14-3

TMA-5
Chemical name 1-(2,3,6-Trimethoxyphenyl)propan-2-amine,
2,3,6-trimethoxyamphetamine
Melting point 124 - 125 °C (hydrochloride)
SMILES NC(C)CC1=C(OC)C=CC(OC)=C1OC
CAS number
20513-16-0

TMA-6
Chemical name 1-(2,4,6-Trimethoxyphenyl)propan-2-amine,
2,4,6-trimethoxyamphetamine
Melting point 207 - 208 °C (hydrochloride)
SMILES NC(C)CC1=C(OC)C=C(OC)C=C1OC
CAS number
15402-79-6
UNII_Ref =  YesY UNII = P2K02L3YON

Chemical data

As they are isomers the TMAs have the same totals 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).[1]

See also

References

  1. ↑ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf
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