Isomescaline
| Clinical data | |
|---|---|
| Other names | 2,3,4-Trimethoxyphenethylamine; 2,3,4-TMPEA; TMPEA-3; 2C-TMA-3; Reciprocal mescaline |
| Routes of administration | Oral[1] |
| ATC code |
|
| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
| Identifiers | |
| |
| CAS Number |
|
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H17NO3 |
| Molar mass | 211.261 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (what is this?) (verify) | |
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
References
- ^ a b c d e f g h i j k Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
- ^ a b c d e 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.
- ^ a b c d e f 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.
- ^ Clark LC, Benington F, Morin RD (May 1965). "The Effects of Ring-Methoxyl Groups on Biological Deamination of Phenethylamines". J Med Chem. 8 (3): 353–355. doi:10.1021/jm00327a016. PMID 14323146.
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.