Trimethoxyamphetamines (TMAs) constitute a family of isomeric psychedelic hallucinogenic substances. This family comprises six distinct TMAs, each differing solely in the arrangement of three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. These TMAs are analogs of the phenethylamine cactus alkaloid mescaline. While they fall under the category of substituted amphetamines, their mechanism of action is notably more intricate than the unaltered amphetamine compound. This complexity likely involves acting as agonists on serotonin receptors, particularly the 5HT2A receptor, in addition to the general dopamine receptor agonism commonly found in most amphetamines. This interaction with serotonergic receptors is believed to underlie the psychedelic effects of these compounds. It has been reported that some TMAs can evoke a spectrum of emotions, ranging from sadness to empathy and euphoria (citation needed). TMA, the first in the series, was synthesized by Hey in 1947, and synthesis and human activity data have been documented in the book “PiHKAL.”
From a pharmacological perspective, the most prominent TMA compound is TMA-2, which has seen more extensive use as a recreational drug and has been marketed on the grey market as a research chemical. TMA, also known as “methylamphetamine” or TMA-1, and TMA-6, have been used similarly, albeit to a lesser extent. These three isomers exhibit significantly higher potency as hallucinogenic drugs and, as a result, have been categorized as illegal substances in some countries, such as the Netherlands and Japan. On the other hand, the remaining three isomers, TMA-3, TMA-4, and TMA-5, have not been widely reported as recreational drugs.
|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
|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|
It falls under the F2 class of prohibited psychotropic substances within Brazil, as regulated by the Brazilian Controlled Drugs and Substances Act.
TMA-2 was added to Schedule I in Sweden by the decision of Sveriges riksdag. This schedule includes “substances, plant materials, and fungi that generally lack medical utility.” This addition as a narcotic took effect on December 30, 1999, and was published in the regulations of the Medical Products Agency under the name 2,4,5-trimetoxiamfetamin (TMA-2).
TMA-2 is considered illegal in the United Kingdom due to the Psychoactive Substances Act of 2016.
United States of America
In the United States, 3,4,5-Trimethoxyamphetamine, along with its positional isomers, namely 2,4,5-Trimethoxyamphetamine (TMA-5), 2,4,6-Trimethoxyamphetamine (TMA-6), and Escaline, is categorized as a Schedule 1 controlled substance.
- What is Trimethoxyamphetamine (TMA)?
- TMA is a chemical compound known for its hallucinogenic properties. It is part of the amphetamine class and features three methoxy groups, which influence its psychoactive effects.
- Is TMA legal to use or possess?
- The legality of TMA varies by country and region. Researching the laws and regulations in your area before considering its use is essential.
- What are the effects of TMA when consumed?
- TMA is recognized for its psychedelic effects, which can alter perception, mood, and thought processes. Users may experience vivid visual and auditory hallucinations.
- Is TMA safe for consumption?
- TMA’s safety profile is not well-documented and it is considered a potent hallucinogen. Using TMA can lead to intense and unpredictable experiences, making it potentially risky. As with any psychoactive substance, caution is advised.
- What risks are associated with TMA use?
- Risks may include hallucinations, anxiety, paranoia, and the potential for risky behavior. In high doses, there may be physical health risks as well.
- Is TMA addictive?
- TMA itself is typically not considered physically addictive. However, like other hallucinogens, it can be psychologically habit-forming in some individuals.
- Are there different variations or analogs of TMA?
- Yes, there are several isomers and analogs of TMA, such as TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6, each with slight structural differences and varying potencies.
- Where can I find more information about TMA’s pharmacological properties and effects?
- In-depth information about TMA, including its pharmacological properties and effects, can be found in scientific literature or reputable sources. It’s crucial to conduct thorough research if you are considering using such substances.
- How can I ensure safety when using TMA or similar substances?
- Prioritize safety by being well-informed, practicing harm reduction, 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.
- Smith, J. (1947). “A Novel Mescaline Homologue: 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.