DOYN

DOYN
Clinical data
Other names4-Ethynyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethynylamphetamine
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action10–15 hours
Identifiers
  • 1-(4-ethynyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
Chemical and physical data
FormulaC13H17NO2
Molar mass219.284 g·mol−1
3D model (JSmol)
  • COc1cc(C#C)c(cc1CC(N)C)OC
  • InChI=1S/C13H17NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h1,7-9H,6,14H2,2-4H3
  • Key:XSBAOBBZMYENRL-UHFFFAOYSA-N

DOYN, also known as 4-ethynyl-2,5-dimethoxyamphetamine, is a serotonergic psychedelic of the phenethylamine, amphetamine, and DOx families. According to Daniel Trachsel, it produces hallucinogenic effects with a dose range of 2 to 6 mg orally and a duration of 10 to 15 hours. The drug's effects are described as typical psychedelic effects including fantasy, imagery, and visuals. It is described as having a relatively short duration compared to 4-alkyl DOx derivatives like DOM, perhaps due to more rapid metabolism. DOYN was first mentioned in the scientific literature by Trachsel in 2003 and was then described in more depth by him in 2013. It is a controlled substance in Canada under phenethylamine blanket-ban language.

See also

References

  1. 1 2 3 4 5 6 7 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 768, 778, 780, 810. ISBN 978-3-03788-700-4. OCLC 858805226. Als Alkinderivat existiert das DOYN (33) als einziger Vertreter. Die Synthese erfolgte in Analogie zu Ref. [411. Es zeigt typische psychedelische Wirkungen begleitet von Fantasy, Imagery und Visuals (Siche Kapitel 8.5.18 für Begriffserklärung) im Bereich von 2—6mg gepaart von einer Wirkdauer von 10—15h. Diese Wirkdauer ist — im Vergleich zu den 4-alkylierten Analoga — eher kurz. Es darf auf einen etwas rascheren Metabolismus (im Bereich der Dreifachbindung) im Vergleich zu DOET (14) spekuliert werden. Das als biphasisch beschriebene Wirkprofil deutet auf aktive Metaboliten hin.
  2. 1 2 Shulgin A, Manning T, Daley PF (2011). "#60. DOM". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 118–129. ISBN 978-0-9630096-3-0. OCLC 709667010.
  3. 1 2 Trachsel D (2003). "Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure–Activity Relationships, Part 3: 4-Ethynyl-2,5-dimethoxyphenethylamine (=4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN)". Helvetica Chimica Acta. 86 (8): 2754–2759. doi:10.1002/hlca.200390224. ISSN 0018-019X. Retrieved 21 June 2025.
  4. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.