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Pharmaceutical compound
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]
^ 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 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs.
2,N ,N -TMT
4,N ,N -TMT
5-Bromo-DMT
5-Chloro-DMT
5-Fluoro-DMT
5-N ,N -TMT
7,N ,N -TMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
6-Fluoro-DMT
Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )
β-Carbolines and Harmala alkaloids (e.g., harmine , harmaline , 6-methoxyharmalan )
Iboga alkaloids (e.g., 18-MAC , 18-MC , coronaridine , ibogaine , ibogamine , ME-18-MC , noribogaine , tabernanthine , voacangine )
Ibogalogs (e.g., ibogainalog )
O -Methylnordehydrobufotenine
Partial ergolines (e.g., NDTDI , RU-28306 , CT-5252 )
Piperidinylethylindoles (e.g., Pip-T )
Pyrrolidinylethylindoles (e.g., Pyr-T , 5-MeO-pyr-T )
Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5-MeO-MPMI )
Benzofurans (e.g., 5-MeO-DiBF , dimemebfe (5-MeO-BFE) , mebfap )
Benzothiophenes (e.g., 3-APBT )
Indazoles (e.g., AL-38022A , O -methyl-AL-34662 )
Indenes (e.g., C-DMT )
Isotryptamines (e.g., 6-MeO-isoDMT , Ro60-0175 )
MYCO-005
Quinolinylethylamines (e.g., mefloquine )
Others: 2C-G-x (e.g., 2C-G-3 , 2C-G-5 )
β-Keto-2C-B (βk-2C-B)
β-Keto-2C-I (βk-2C-I)
β-Methyl-2C-B (BMB)
(e.g., BOB , BOD , BOH-2C-B )
(e.g., HOT-2 , HOT-7 , HOT-17 )
N -Ethyl-2C-B
(e.g., 2CD-2-ETO , 2CD-5-ETO , 2CE-5-ETO , 2CE-5iPrO , 2CT2-5-ETO , ASR-2001 (2CB-5PrO) )
Others
2-TOET
2-TOM
25B-NAcPip
4-HA
5-TOET
5-TOM
Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F-2 , F-22 )
Benzothiophenes (e.g., 5-APBT , 6-APBT )
CT-5172
DMAs (e.g., 2,4-DMA , 3,4-DMA )
Fenfluramine
MMA (3-MeO-4-MA)
Norfenfluramine
(e.g., 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )
PMA (4-MA)
(e.g., TMA-3 , TMA-4 , TMA-5 , TMA-6 )
TOMSO
ZDCM-04
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )
2-Aminoindanes (e.g., DOM-AI )
3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )
Benzazepines (e.g., lorcaserin )
Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
DMBMPP (juncosamine)
Ergolines /lysergamides (e.g., LSD )
Glaucine
IHCH-7113
Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )
Phenylcyclopropylamines (e.g., DMCPA , TMT )
Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )
Z3517967757
ZC-B
Others
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP )
Dihydrobenzoxazines (e.g., efavirenz )
Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )
Quinazolinylethylamines (e.g., RH-34 )
Natural sources
Tryptamines: Acacia spp. (e.g., Acacia acuminata , Acacia confusa )
Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna) , Dipolopterys cabrerana (chaliponga, chacruna) , Mimosa tenuiflora (Mimosa hostilis ; jurema) )
Brosimum (e.g., Brosimum acutifolium (takini) )
Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene) , Anadenanthera colubrina (vilca, cebil) )
Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)
Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis , Psilocybe mexicana (teonanacatl) )
Lysergamides: Achnatherum robustum (sleepy grass)
Epichloë spp.
Ergot (Claviceps ) (e.g., Claviceps purpurea , Claviceps paspali )
Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea ) , Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa ) , Argyreia nervosa (Hawaiian baby woodrose; HBWR) )
Periglandula spp. (e.g., Periglandula ipomoeae , Periglandula clandestina )
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized phenethylamines
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , jimscaline )
2-ADN
2-Benzhydrylpyrrolidine
3-Benzhydrylmorpholine
3-Phenylpiperidines (e.g., 3-phenylpiperidine , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 )
6-AB
AL-1095
Aminochromes (e.g., adrenochrome , adrenolutin )
Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )
Benzocyclobutenes (e.g., 2CBCB-NBOMe , S33005 , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
Butyltolylquinuclidine
Cypenamine (trans -2-phenylcyclopentylamine)
Diphenidine
Diphenylprolinol
DMBMPP
Ergolines (e.g., LSD )
GYKI-52895
HDMP-29
Ivabradine
Lumateperone and analogues (e.g., IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )
Methoxphenidine
Methylmorphenate
Milnacipran
MT-45
2-Naphthylamine
Org 6582
Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )
PF-592,379
Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )
Tetrahydrobenzopyranylamines (e.g., CT-5126 )
Tricyclics (e.g., benzoctamine , dizocilpine )
Z3517967757
ZC-B
Related compounds
2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )
Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )
Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )
Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )
Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )
Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )
Phenylalkenylamines (e.g., phenylbutenamine )
Phenylalkynylamines (e.g., phenylbutynamine )
Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )
Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )
Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )