Isomescaline
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| Other names | 2,3,4-Trimethoxyphenethylamine; 2,3,4-TMPEA; TMPEA-3; 2C-TMA-3; Reciprocal mescaline |
| Routes of administration | Oral[1] |
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| Duration of action | Unknown[1] |
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| Formula | C11H17NO3 |
| Molar mass | 211.261 g·mol−1 |
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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]