2,3,5-Trimethoxyamphetamine

TMA-4
Clinical data
Other names2,3,5-TMA; TMA-4
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action~6 hours[1]
Identifiers
  • 1-(2,3,5-trimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C(=CC(=C1)OC)OC)OC)N
  • InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3
  • Key:MJIBJXKJBRLSQA-UHFFFAOYSA-N

2,3,5-Trimethoxyamphetamine (2,3,5-TMA), also known as TMA-4, is a psychedelic drug of the phenethylamine and amphetamine families.[1][2] It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1).[1][2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,5-TMA's dose as greater than 80 mg orally and its duration as perhaps or about 6 hours.[1][3][4] Based on limited testing, it produced threshold effects including much introspection among others, along with no subjective physical symptoms.[1][2] The drug at 80 mg was described as comparable to 50 μg LSD or 120 mg TMA and as being roughly 4-fold as potent as mescaline.[1][2] Per Shulgin, more testing is needed to fully characterize the drug in humans.[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2,3,5-TMA shows affinity for serotonin receptors.[2][5][6] The drug substitutes for DOM in rodent drug discrimination tests.[2][7]

Chemistry

Synthesis

The chemical synthesis of 2,3,5-TMA has been described.[1][2]

History

2,3,5-TMA was first described in the scientific literature by Alexander Shulgin in 1966.[8] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Society and culture

Canada

2,3,5-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.[9]

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,5-TMA is a Schedule I controlled substance in the United States.[2]

See also

References

  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal160.shtml
  2. ^ a b c d e f g h Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
  4. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  5. ^ Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews. 6 (4): 489–497. doi:10.1016/0149-7634(82)90030-6. PMID 6757811.
  6. ^ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  7. ^ Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacology, Biochemistry, and Behavior. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  8. ^ Shulgin AT (May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry. 9 (3): 445–446. doi:10.1021/jm00321a058. PMID 5960939.
  9. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
allikas: https://en.wikipedia.org/wiki/TMA-4_(psychedelic)