3-Thiosymbescaline
| Clinical data | |
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| Other names | 3-TSB; 3-Ethylthio-4-methoxy-5-ethoxyphenethylamine; 3-EtS-4-MeO-5-EtO-PEA |
| Routes of administration | Oral[1] |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
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| ChEMBL | |
| Chemical and physical data | |
| Formula | C13H21NO2S |
| Molar mass | 255.38 g·mol−1 |
| 3D model (JSmol) | |
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3-Thiosymbescaline (3-TSB), also known as 3-ethylthio-4-methoxy-5-ethoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of symbescaline in which the ethoxy group at the 3 position has been replaced with an ethylthio group.[1][2][3][4] The compound is one of two possible thiosymbescaline (TSB) positional isomers, the other being 4-thiosymbescaline (4-TSB).[1][2][3][4]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-TSB's dose as greater than 200 mg orally and its duration as unknown.[1][2][3] The compound produced no effects whatsoever at a dose of up to 200 mg orally.[1]
The chemical synthesis of 3-TSB has been described.[1][4]
3-TSB was first described in the scientific literature by Shulgin and Peyton Jacob III in 1984.[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]
See also
References
- ^ a b c d e f g h i Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal176.shtml
- ^ a b c d 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 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.
- ^ a b c d e Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". J Med Chem. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431.