Summary
Trimethoxyamphetamines (TMAs) comprise a group of isomeric psychedelic hallucinogenic substances. There are six distinct TMAs, differentiated solely by the arrangement of three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. These compounds are analogs of mescaline, a phenethylamine cactus alkaloid. TMAs are substituted amphetamines, and their action mechanism is more intricate than the unaltered amphetamine compound. This complexity likely involves acting as an agonist on serotonin receptors, such as the 5HT2A receptor, and the typical generalized dopamine receptor agonism seen in most amphetamines. This interaction with serotonergic receptors is thought to underlie the psychedelic effects of TMAs. Some reports suggest that various TMAs can elicit emotions, from sadness to empathy and euphoria.
TMA was first synthesized by Hey in 1947, and synthesis and human activity data can be found in the book “PiHKAL.”
From a pharmacological perspective, TMA-2 is the most notable TMA compound, as it has seen more widespread recreational use and has been marketed on the grey market as a “research chemical.” TMA (sometimes referred to as “methylamphetamine” or TMA-1) and TMA-6 have also been used for this purpose, albeit to a lesser extent. These three isomers are significantly more potent as hallucinogenic drugs and have been classified as illegal in certain countries, such as the Netherlands and Japan. The remaining three isomers, TMA-3, TMA-4, and TMA-5, have not been extensively used as recreational drugs.
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 UNII_Ref = UNII = P2K02L3YON | 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 UNII_Ref = UNII = 713Z3SL0TJ | 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 UNII_Ref = UNII = 9T3SO4A6HM |
| 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 UNII_Ref = UNII = LEL94CV318 | 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 UNII_Ref = UNII = E0NJ557A3E | 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 = UNII = 2X84DCO6GA |
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
Brazil
In Brazil, under the Brazilian Controlled Drugs and Substances Act, 3,4,5-Trimethoxyamphetamine is categorized in the F2 class, including prohibited psychotropics.
Sweden
The Swedish Parliament, Sveriges Riksdag, included TMA-2 in Schedule I, encompassing substances, plant materials, and fungi with no recognized medical use. This classification as narcotics in Sweden was enacted on December 30, 1999, and it is documented in the regulations of the Medical Products Agency under the label 2,4,5-trimetoxiamfetamin (TMA-2).
United Kingdom
The Psychoactive Substances Act of 2016 renders 3,4,5-Trimethoxyamphetamine illegal in the United Kingdom.
United States of America
3,4,5-Trimethoxyamphetamine, alongside its positional isomers, 2,4,5-Trimethoxyamphetamine (TMA-5), 2,4,6-Trimethoxyamphetamine (TMA-6), and Escaline, is classified as a Schedule 1 controlled substance in the United States of America.
FAQ
- What is Trimethoxyamphetamine (TMA)?
- TMA is a compound in the amphetamine class, characterized by three methoxy groups. It is known for its psychoactive properties and hallucinogenic effects.
- Is TMA legal in any country?
- The legality of TMA varies by country. In the United States, it is classified as a Schedule 1 controlled substance; in many other countries, it is also subject to legal restrictions. It is essential to research the specific laws and regulations in your region.
- What are the effects of TMA when consumed?
- TMA is known for its hallucinogenic effects, including perception, mood, and thought alterations. Users may experience vivid visual and auditory hallucinations.
- Is TMA safe to use?
- The safety of TMA is not well-established, and it is considered a potent hallucinogen. It can lead to intense and potentially unpredictable experiences. Using TMA can be risky, and it is generally discouraged.
- What are the risks associated with TMA use?
- Risks include hallucinations, anxiety, paranoia, and the potential for dangerous behavior. In high doses, it may also pose physical health risks.
- Is TMA addictive?
- TMA itself is not typically considered physically addictive. However, like other hallucinogens, it can be psychologically habit-forming in some individuals.
- What is the legal status of TMA in the United States?
- In the United States, TMA is classified as a Schedule 1 controlled substance, making its possession and distribution illegal.
- Are there any variations or analogs of TMA?
- Yes, there are various isomers and analogs of TMA, such as TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6, which have slight structural differences and varying potencies.
- Where can I find more information about TMA’s pharmacological properties and effects?
- Detailed information on TMA, including its pharmacological properties and effects, may be available in scientific literature or through reputable sources. It’s essential to conduct thorough research if you are considering experimenting with such substances.
- How can I ensure safety when using TMA or similar substances?
- Prioritize safety by being well-informed, using harm reduction practices, and seeking guidance from healthcare professionals or harm reduction organizations. Always be aware of the legal status and potential risks associated with the substance in your region.
References
- Hey, P. (1947). “Novel Homologue of Mescaline: Synthesis and Discovery.” Published in the Quarterly Journal of Pharmacy and Pharmacology, Volume 20(2), Pages 129–134. PMID: 20260568.
- Anvisa (2023-07-24). “Collegiate Board Resolution No. 804 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control” (in Brazilian Portuguese). Retrieved from Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Accessed on 2023-08-27.
- For information on TMA-2’s scheduling in Sweden, please refer to the official document: Swedish Medical Products Agency Regulation LVFS 2004:3 (PDF).
- To understand the legal status of TMA in the United States, consult the Controlled Substances Act’s Orange Book.