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Metaproscaline

Metaproscaline
Clinical data
Other namesMP; 3,4-Dimethoxy-5-propoxyphenethylamine; 3-Propoxy-4,5-dimethoxyphenethylamine
Routes of
administration		Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 2-(3,4-dimethoxy-5-propoxyphenyl)ethanamine
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(cc1OCCC)CCN)OC
  • InChI=1S/C13H21NO3/c1-4-7-17-12-9-10(5-6-14)8-11(15-2)13(12)16-3/h8-9H,4-7,14H2,1-3H3 checkY
  • Key:LRMHEQAATQTVRI-UHFFFAOYSA-N checkY
  (verify)

Metaproscaline (MP), also known as 3,4-dimethoxy-5-propoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the derivative of mescaline in which the methoxy group at the 3 position has been replaced with a propoxy group.[1][2][3][4] In addition, it is a positional isomer of proscaline.[1][2][3][4]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists metaproscaline's dose as greater than 240 mg orally and its duration as unknown.[1][2][3] The drug produced no clear effects at tested doses of up to 240 mg orally.[1]

The chemical synthesis of metaproscaline has been described.[1] Analogues of metaproscaline include mescaline, proscaline, and metaescaline, among others.[1][2][3][4]

Metaproscaline 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] The drug is not a controlled substance in Canada as of 2025.[5]

See also

References

  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (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/pihkal137.shtml
  2. ^ 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.
  3. ^ a b c d e 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. ^ 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.
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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