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") 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

Chemical data

As they are isomers the TMAs have the same totals formula, C₁₂H₁₉NO₃, and the same molecular mass, 225.28 g/mol.

Properties

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, 1899, published by Medical Products Agency in their regulation LVFS 2004:3 listed as 2,4,5-trimetoxiamfetamin (TMA-2).^[1]

See also

• Psychedelic
• Hallucinogenic drug
• Phenethylamines
• Amphetamines
• Recreational drug use
• 2,5-Dimethoxy-4-Substituted Amphetamines

References

External links

• PiHKAL 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