2,3,6-Trimethoxyamphetamine

Last updated

2,3,6-Trimethoxyamphetamine
Trimethoxyamphetamine-5.svg
Clinical data
Other names2,3,6-TMA; TMA-5
Routes of
administration 		Oral [1] [2]
Drug class Serotonergic psychedelic; Hallucinogen; Stimulant
ATC code
  • None
Pharmacokinetic data
Duration of action 8–10 hours [1] [2]
Identifiers
  • 1-(2,3,6-trimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C12H19NO3
Molar mass 225.288 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=CC(=C1OC)OC)OC)N
  • InChI=1S/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
  • Key:OASZJWLOOFXASO-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]

Contents

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

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

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. 1 2 3 4 5 6 7 8 9 10 11 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/pihkal161.shtml
  2. 1 2 3 4 5 6 7 8 9 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. 1 2 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. 1 2 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 (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.
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