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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 exhibit 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.

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 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.

Contents 1 TMAs 2 Chemical data 3 Properties 4 See also 5 Categorization 6 External links

[edit] 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	<center/>

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	<center>

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

[edit] Chemical data

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

[edit] 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

[edit] See also

• Psychedelic
• Hallucinogenic drug
• Phenethylamines
• Amphetamines
• Recreational drug use

[edit] Categorization

.

[edit] External links

• PIHKAL entries:
  • TMA
  • TMA-2
  • TMA-3
  • TMA-4
  • TMA-5
  • TMA-6
• Erowid TMA vault
• EMCDDA Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs

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This page uses content from the English-language version of Wikipedia. The original article was at Trimethoxyamphetamine. The list of authors can be seen in the page history. As with Psychology Wiki, the text of Wikipedia is available under the GNU Free Documentation License.