Symbescaline

Symbescaline
Clinical data
Other namesSB; 3,5-Diethoxy-4-methoxyphenethylamine
Routes of
administration		Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 2-(3,5-diethoxy-4-methoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
  • COc1c(cc(cc1OCC)CCN)OCC
  • InChI=1S/C13H21NO3/c1-4-16-11-8-10(6-7-14)9-12(17-5-2)13(11)15-3/h8-9H,4-7,14H2,1-3H3 Y
  • Key:ROKMKYBLAPLLER-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Symbescaline (SB), also known as 3,5-diethoxy-4-methoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline.[1][2][3] It is the analogue of mescaline in which the methoxy groups at the 3 and 5 positions have been replaced with ethoxy groups.[1][2][3] In addition, symbescaline is a positional isomer of asymbescaline.[1][2][3]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists symbescaline's dose as above 240 mg orally and its duration as unknown.[1][2][3] The effects of symbescaline have been reported to include no effects, a vague threshold, a slight chill, and strange and disrupted sleep.[1] It is said to have a very unpleasant taste.[1] Shulgin concluded that symbescaline is "probably not active".[1]

The chemical synthesis of symbescaline has been described.[1]

Symbescaline was first described in the scientific literature by Alexander 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

  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (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/pihkal144.shtml
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. Archived from the original on 2025-07-12.
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