Chemistry:Isomescaline
Isomescaline (IM), also known as 2,3,4-trimethoxyphenethylamine (2,3,4-TMPEA) or as TMPEA-3 or 2C-TMA-3, is a chemical compound of the phenethylamine and scaline families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine; 2,3,4-TMPEA).[1][2][3] It is one of several possible positional isomers of trimethoxyphenethylamine (TMPEA).[1][2][3] In addition, it is the positional isomer of mescaline in which the methoxy groups on the phenyl ring are located at the 2, 3, and 4 positions instead of at the 3, 4, and 5 positions.[1][2][3]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists isomescaline's dose as greater than 400 mg orally and its duration as unknown.[1][2][3] The compound produced no effects at tested doses of up to 400 mg orally in humans.[1] It was concluded that isomescaline is inactive.[1][3]
The chemical synthesis of isomescaline has been described.[1] Analogues of isomescaline include 2,3,4-trimethoxyamphetamine (2,3,4-TMA; TMA-3; α-methylisomescaline) and the thioisomescaline (TIM) compounds, among others.[1][2][3]
Isomescaline was first described in the scientific literature by L. Clark and colleagues by 1965.[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1] Isomescaline is not a controlled substance in Canada as of 2025.[5]
See also
- Trimethoxyphenethylamine
- Substituted methoxyphenethylamine
- Scaline
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 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.
- ↑ 2.0 2.1 2.2 2.3 2.4 "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.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "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.
- ↑ "The Effects of Ring-Methoxyl Groups on Biological Deamination of Phenethylamines". J Med Chem 8 (3): 353–355. May 1965. doi:10.1021/jm00327a016. PMID 14323146.
- ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html.
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