Propynyl (drug)

Propynyl
Clinical data
Other namesPROPYNYL; 4-Propynyloxy-3,5-dimethoxyphenethylamine; Propynylmescaline; Propynylscaline
Routes of
administration
Oral[1]
Drug classPsychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of action8–12 hours[1]
Identifiers
  • 2-{3,5-dimethoxy-4-[(prop-2-yn-1-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H17NO3
Molar mass235.283 g·mol−1
3D model (JSmol)
  • COc1cc(cc(OC)c1OCC#C)CCN
  • InChI=1S/C13H17NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h1,8-9H,5-7,14H2,2-3H3 Y
  • Key:KNIWBMMJSJHUJB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Propynyl, also known as 4-propynyloxy-3,5-dimethoxyphenethylamine or as propynylscaline, is a psychoactive drug of the scaline family related to mescaline.[1][2][3] It is the derivative of mescaline in which the methoxy group at the 4 position has been replaced with a propynyloxy group.[1][2][3]

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists propynyl's dose as 80 mg or more orally and its duration as 8 to 12 hours.[1] The effects of propynyl have been reported to include "[not] that much mental stuff", obviously altered behavior, body load, physical fuzziness, cold feet, and next-day hangover or after-effects such as sluggishness.[1] The drug produced no visual changes or closed-eye visuals, and clear hallucinogenic effects were not described.[1] Higher doses than 80 mg orally were not explored, but there was no suggestion of value in exploring higher levels.[1]

The chemical synthesis of propynyl has been described.[1] Analogues of propynyl include mescaline, escaline, proscaline, allylescaline, and methallylescaline, among others.[1][2][3]

Propynyl was first described in the literature by Shulgin in PiHKAL in 1991.[1] It is not a controlled substance in Canada as of 2025.[4]

See also

References

  1. ^ 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. Propynyl entry
  2. ^ a b c 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 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. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.