DOYN

DOYN
Clinical data
Other names	4-Ethynyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethynylamphetamine
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	10–15 hours
Identifiers
	IUPAC name 1-(4-ethynyl-2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	633290-70-7;
PubChem CID	171652344;
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(C#C)c(cc1CC(N)C)OC;
	InChI 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.^[1]^[2]^[3] According to Daniel Trachsel, it produces hallucinogenic effects with a dose range of 2 to 6 mg and a duration of 10 to 15 hours.^[1] The drug's effects are described as typical psychedelic effects including fantasy, imagery, and visuals.^[1] It is described as having a relatively short duration compared to 4-alkyl DOx derivatives like DOM, perhaps due to more rapid metabolism.^[1] DOYN was first mentioned in the scientific literature by Trachsel in 2003 and was then described in more depth by him in 2013.^[1]^[2]^[3]

References

^ ^a ^b ^c ^d ^e ^f ^g 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.
^ ^a ^b 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.
^ ^a ^b 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.