2,3,6-Trimethoxyamphetamine
Drug nameTMA-5
Width175px
Routes of administrationOral[1][2]
ClassSerotonergic psychedelic; Hallucinogen; Stimulant
Atc prefixNone
Duration of action8–10 hours[1][2]
Cas number20513-16-0
Pubchem31013
Chemspiderid28772
UniiE0NJ557A3E
Chembl125134
Synonyms2,3,6-TMA; TMA-5
Iupac name1-(2,3,6-trimethoxyphenyl)propan-2-amine
C12
H19
N1
O3
SmilesCC(CC1=C(C=CC(=C1OC)OC)OC)N
Stdinchi1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3
StdinchikeyOASZJWLOOFXASO-UHFFFAOYSA-N

2,3,6-Trimethoxyamphetamine (2,3,6-TMA), also known as TMA-5, is a psychedelic drug and mild stimulant 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 2,3,6-TMA's dose as approximately 30 mg or more orally and its duration as 8 to 10 hours.[1][2][3][4] Based on limited testing, the effects of 2,3,6-TMA were reported to include intense introspection, mild stimulation, and pupil dilation, among others.[1] The drug was said to be comparable to about 75 μg or more LSD.[1] It is approximately 10 times more potent than mescaline.[1][3][4] However, it was noted that more testing was needed.[1]

Interactions

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

Pharmacology

Pharmacodynamics

Unlike the other TMA isomers, 2,3,6-TMA was not tested at serotonin receptors or in rodent drug discrimination tests.[5][6][7][8]

Chemistry

Synthesis

The chemical synthesis of 2,3,6-TMA has been described.[1][2]

History

2,3,6-TMA was first described in the scientific literature by Alexander Shulgin in 1966.[2][9] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[2][1]

Society and culture

Canada

2,3,6-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.[10]

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,6-TMA is a Schedule I controlled substance in the United States.[2]

See also

References

  1. ^ https://erowid.org/library/books_online/pihkal/pihkal161.shtml
  2. ^ 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". Hallucinogens: An Update. Vol. 146. National Institute on Drug Abuse Research Monograph Series. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived 13 July 2025 at the Wayback Machine.
  4. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived 13 July 2025 at the Wayback Machine.
  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 (June 1986). "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug and Alcohol Dependence. 17 (2–3): 119–134. doi:10.1016/0376-8716(86)90003-7. PMID 2874967
  8. ^ 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
  9. ^ Shulgin AT (May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry. 9 (3): 445–446. doi:10.1021/jm00321a058. PMID 5960939
  10. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.