Chemistry:2,3,4-Trimethoxyamphetamine

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2,3,4-Trimethoxyamphetamine (2,3,4-TMA), also known as TMA-3 or as α-methylisomescaline, is a putative 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]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,4-TMA's dose as greater than 100 mg orally and its duration as unknown.[1][2][3][4] The drug produced no effects whatsoever at a dose of 100 mg in three separate individuals.[1] Higher doses were not tested, but 2,3,4-TMA could possibly be active at higher doses.[1]

Interactions

Pharmacology

Pharmacodynamics

2,3,4-TMA shows affinity for serotonin receptors.[5][2][6][7] It substituted for DOM in rodent drug discrimination tests.[2][8]

Chemistry

Synthesis

The chemical synthesis of 2,3,4-TMA has been described.[1][2]

History

2,3,4-TMA was first described in the scientific literature by Alexander Shulgin in 1964.[2][9][10] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2]

Society and culture

Canada

2,3,4-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.[11]

United States

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

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  https://erowid.org/library/books_online/pihkal/pihkal159.shtml
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. 
  3. ↑ "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. 
  4. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  5. ↑ "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews 6 (4): 489–497. 1982. doi:10.1016/0149-7634(82)90030-6. PMID 6757811. 
  6. ↑ "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry 23 (3): 294–299. March 1980. doi:10.1021/jm00177a017. PMID 7365744. 
  7. ↑ "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence 60 (2): 121–132. August 2000. doi:10.1016/s0376-8716(99)00148-9. PMID 10940539. 
  8. ↑ "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacology, Biochemistry, and Behavior 17 (4): 603–607. October 1982. doi:10.1016/0091-3057(82)90330-6. PMID 6965276. 
  9. ↑ "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia 20 (7): 366–367. July 1964. doi:10.1007/BF02147960. PMID 5855670. 
  10. ↑ "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)". Journal of Medicinal Chemistry 9 (3): 445–446. May 1966. doi:10.1021/jm00321a058. PMID 5960939. 
  11. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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