Psychedelic drug
Pharmaceutical compound
4-HO-DET , also known as4-hydroxy-N ,N -diethyltryptamine as well asethocin orCZ-74 , is apsychedelic drug of thetryptamine and4-hydroxytryptamine families related topsilocin (4-HO-DMT).[ 1] orally .[ 1]
The drug acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A receptor among others.[ 4] [ 5] [ 6] [ 5] structurally related to other psychedelic tryptamines such as psilocin,diethyltryptamine (DET), and4-HO-MET .[ 1] [ 7] Ethocybin (4-PO-DET; CEY-19) and4-AcO-DET are assumed to act asprodrugs of 4-HO-DET.[ 1] [ 5]
4-HO-DET was first described in the literature by 1963.[ 8] [ 9] [ 5] Sandoz byAlbert Hofmann and colleagues.[ 8] [ 5] psychedelic-assisted psychotherapy byHanscarl Leuner and colleagues in the 1960s.[ 10] [ 1] [ 9] Alexander Shulgin in his 1997 bookTiHKAL Tryptamines I Have Known and Loved ).[ 1] designer drug in 2005.[ 11]
In his bookTiHKAL Tryptamines I Have Known and Loved ) and other publications,Alexander Shulgin variably lists the dose range of 4-HO-DET as 10 to 25 mgorally , either as 4-HO-DET itself or as presumedprodrugs likeethocybin (4-PO-DET) or4-AcO-DET , and itsduration as 2 to 6 hours.[ 1] [ 12] [ 2] [ 13] [ 14] [ 10] [ 3] mg, whereas loss of contact with reality is said to occur at doses over 30 mg.[ 15] [ 2] mg of ethocybin.[ 1] mg.[ 12] onset of 4-HO-DET is described as being around 30 to 45 minutes.[ 1]
The drug has been reported to be very similar topsilocin andpsilocybin in its qualitative effects but to be somewhat shorter in duration, for instance as short as 2 to 3 hours.[ 16] [ 2] [ 10] [ 3] closed-eye visuals ,open-eye visuals such as fire light turning into bursts of color, potential for intensepsychedelic visuals ,auditory hallucinations ,time dilation , temporal andspatial disorientation ,body image disturbance,musical immersion,derealization ,ego death , feeling like one has ceased to exist, feelings of oneness with the universe or reality,ineffability , "sparkly-ness", powerful emotions including feelings of intense love, peace, acceptance, awe, reverence, and joy, feelings ofsadness , uncomfortableness, and feeling overwhelmed.[ 1]
Other effects included feelingintoxicated ,sedation ,restlessness ,loss of language ability ,impaired concentration , compulsion to talk and interact with others, and lack oferotic feelings.[ 1] psychosis ,depersonalization ,mystical experiences ,delirium ,schizophrenia -like behavior,catatonia , andparanoia have been found to occur.[ 1] stomach andabdominal discomfort ,appetite loss ,jaw tightening ,body tremors ,motor incoordination , body disturbance,diuretic effects, and increasedblood pressure .[ 1]
4-HO-DET activities Target Affinity (Ki , nM) 5-HT1A 396–1,840 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy ) 5-HT1B 2,242 5-HT1D 585 5-HT1E 568 5-HT2A 269–400 (Ki )a (EC50 )a –100% ( Emax ) 5-HT2B 73 (Ki )EC50 ) Emax ) 5-HT2C 388–436 (Ki )a –264 (EC50 )a ( Emax ) 5-HT5A 1,429 5-HT6 230 5-HT7A 826 α2A –α2C IA D2 –D5 IA H1 1,079 H2 9,984 M4 IA σ1 IA σ2 3,026 NR2B 8,720 SERT Tooltip Serotonin transporter 1,411–1,800 (Ki )IC50 ) DAT Tooltip Dopamine transporter IA Notes: The smaller the value, the more avidly drug interacts with the site.Footnotes: a = Stimulation ofIP1 Tooltip inositol phosphate formation.Sources: [ 4] [ 5] [ 6] [ 17]
4-HO-DET acts as apotent non-selective serotonin receptor agonist , including of theserotonin 5-HT2A ,5-HT2B , and5-HT2C receptors .[ 4] [ 5] [ 6] serotonin reuptake inhibitor , with lowaffinity but moderate potency.[ 4] targets , includingadrenergic receptors (α2A - ,α2B ,α2C ),dopamine receptors (D2 –D5 ),muscarinic acetylcholine receptors (M4 ), and thedopamine transporter (DAT).[ 6]
It induces thehead-twitch response , a behavioral proxy ofpsychedelic effects, in rodents.[ 5] psilocin .[ 5]
4-HO-DET, also known as 4-hydroxy-N ,N -diethyltryptamine, is asubstituted tryptamine and4-hydroxytryptamine .[ 1] hydroxy derivative ofN ,N -diethyltryptamineanalogue ofpsilocin (4-hydroxy-N ,N -dimethyltryptamine; 4-HO-DMT).[ 1]
Thechemical synthesis of 4-HO-DET has been described.[ 1]
4-HO-DET is theN ,N -diethyl analogue ofpsilocin (4-HO-DMT).[ 1] diethyltryptamine (DET),5-MeO-DET ,4-HO-DPT ,4-HO-MET ,4-HO-EPT , and5-HO-DET , among others.[ 1] acetate ester of 4-HO-DET is known as4-AcO-DET and thephosphate ester is known asethocybin (4-PO-DET or CEY-19).[ 1] [ 5] prodrugs of 4-HO-DET, as has been shown with the acetate and phosphate esters of other methylated tryptamines such as psilocin (e.g.,psilocybin (4-PO-DMT) and4-AcO-DMT ).[ 1] [ 18] [ 5]
4-HO-DET was first described in the literature by 1963.[ 8] [ 9] Albert Hofmann and Franz Troxler atSandoz in the 1950s and went by the developmental code nameCZ-74 .[ 8] [ 5] [ 3] prodrug ethocybin (4-PO-DET; CEY-19), 4-HO-DET was one of the earlieststructurally modified orsynthetic psychedelic tryptamines to be developed.[ 16] [ 3] clinical studies ofpsychedelic-assisted psychotherapy by theGerman researchersHanscarl Leuner and Gerhard Baer in the 1960s.[ 10] [ 1] [ 9] synthesized and studied, along with many other4-hydroxytryptamines , byDavid Repke and colleagues in the 1970s and 1980s.[ 19] [ 20] Alexander Shulgin in his 1997 bookTiHKAL Tryptamines I Have Known and Loved ).[ 1] designer drug inEurope in 2005.[ 11]
Society and culture [ edit ] Scheduled in the "government decree on psychoactive substances banned from the consumer market".[ 21]
Sveriges riksdags Statens folkhälsoinstitut Lagen om förbud mot vissa hälsofarliga varor Act on the Prohibition of Certain Goods Dangerous to Health ) as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 4-hydroxi-N,N-diethyltryptamin (4-HO-DET), making it illegal to sell or possess.[ 22]
4-HO-DET is unscheduled in the United States, but purchase, sale, or possession for human consumption could be prosecuted under theFederal Analogue Act .[ 23]
4-HO-DET, under the code name CZ-74 and along withethocybin (CEY-19), has been studied inpsychedelic-assisted psychotherapy .[ 10] [ 1] [ 9]
^a b c d e f g h i j k l m n o p q r s t u v w x y z Shulgin A, Shulgin A (September 1997)."#16 4-HO-DET" .Isomer Design . Transform Press. Retrieved28 November 2023 . ^a b c d Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.).Psychopharmacological Agents: Use, Misuse and Abuse 59– 146.doi :10.1016/b978-0-12-290559-9.50011-9 .ISBN 978-0-12-290559-9 Although the N-dealkylated homologs are as yet untested clinically, the N,N-diethyl homologs of psilocybin and of psilocin have been studied in man (Leunder and Baer, 1965). These compounds [CEY-19, (XXXIII); CZ-74, (XXXIV)] in dosages of from 5 to 20 mg appear to resemble psilocybin in the qualitative nature of their action but to be of shorter duration. Maximum effects are obtained in an hour, and 2 hours later the subject is for the most part recovered, thus providing a valuable time course for psychiatric therapy. ^a b c d e Ross S, Franco S, Reiff C, Agin-Liebes G (9 March 2021). "Psilocybin". In Grob CS, Grigsby J (eds.).Handbook of Medical Hallucinogens 181– 214.ISBN 978-1-4625-4544-5 Sandoz began manufacturing and distributing pure synthetic psilocybin pills (under the name Indocybin) to curious physicians and researchers around the world and would do so until recalling the drug in 1965 due to a growing political backlash in the United States (Hofmann, 2005). Sandoz also produced two synthetic drugs derived from mushroom-extracted psilocybin, CZ-74 (4-hydroxy-N,N-diethyltryptamine) and CEY-19 (4-phosphoryloxy-N,N-diethyltryptamine), both of which are shorter (approximately 3 hours in duration) acting than psilocybin (Baer, 1967). [...] ^a b c d Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023)."Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2A R), 5-HT2C R, 5-HT1A R, and Serotonin Transporter" .The Journal of Pharmacology and Experimental Therapeutics .385 (1):62– 75.doi :10.1124/jpet.122.001454 .PMC 10029822 PMID 36669875 . ^a b c d e f g h i j k l Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. (April 2021)."Investigation of the Structure-Activity Relationships of Psilocybin Analogues" .ACS Pharmacology & Translational Science .4 (2):533– 542.doi :10.1021/acsptsci.0c00176 .PMC 8033608 PMID 33860183 .Following the isolation of psilocybin and psilocin by Hofmann and colleagues in 1957,34 various 4-substituted tryptamines were reported in the literature. For example, Hofmann synthesized 4-hydroxy-N,N-diethyltryptamine (CZ-74, 4-HO-DET) and 4-phosphoryloxy-N,N-diethyltryptamine (CEY-19).75 Similar to psilocybin and psilocin, CEY-19 and CZ-74 have equivalent molar potencies in humans.3,50 ^a b c d Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (April 2023)."Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N -dimethyltryptamine in Mice" .ACS Pharmacology & Translational Science .6 (4):567– 577.doi :10.1021/acsptsci.2c00222 .PMC 10111620 PMID 37082754 . ^ Greene SL (2021)."Tryptamines" . In Dargan PI, Wood DM (eds.).Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (Second ed.). London, United Kingdom: Academic Press. p. 499.ISBN 978-0-12-819030-2 ^a b c d US patent 3075992 , Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29 ^a b c d e Leuner H, Baer G (1965)."Two new short-acting hallucinogens of the psilocybin group" .Neuropsychopharmacology .4 :471– 474. Archived fromthe original on 2025-04-22. ^a b c d e Passie T (7 November 2022). "History of the Use of Hallucinogens in Psychiatric Treatment". In Grob CS, Grigsby J (eds.).Handbook of Medical Hallucinogens 95– 118.ISBN 978-1-4625-5189-7 Psycholytic therapy underwent a number of modifications during its active years. Some European therapists experimented with shorter-acting psilocybin derivatives such as CZ-74 (4-hydroxy-N,N-diethyltryptamine, also known as 4-HO-DET; Baer, 1967; Shulgin & Shulgin, 2014), which has a duration of 4—6 hours and is phenomenologically similar to LSD; CEY-19 (phosphoryloxy-N,N-diethyltryptamine, also known as 4-PO-DET or ethocybin), which has a duration of 2—4 hours and is also similar to LSD, and the mescaline derivative 2-CD (2,5-dimethoxy-4-methylphenethylamine; Schlichting, 1989). Therapists in the United States experimented with the short-acting dipropyltrytamine (DP T) in psycholytic therapy (Soskin, 1975; Soskin, Grof, & Richards, 1973), as well as in psychedelic therapy (Richards, Rhead, DiLeo, Yensen, & Kurland, 1977). ^a b "EMCDDA–Europol Annual Report on the implementation of Council Decision 2005/387/JHA" .European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) .^a b Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020)."Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF) .Neuropharmacology .167 107933.doi :10.1016/j.neuropharm.2019.107933 .PMC 9191653 PMID 31917152 .Table 4 Human potency data for selected hallucinogens. [...] ^ Jacob P, Shulgin AT (1994)."Structure-activity relationships of the classic hallucinogens and their analogs" .NIDA Research Monograph .146 :74– 91.PMID 8742795 . ^ Shulgin AT (2003)."Basic Pharmacology and Effects" . In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook 67– 137.ISBN 978-0-12-433951-4 ^ Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview".Neuroscience and Biobehavioral Reviews .6 (4):489– 497.doi :10.1016/0149-7634(82)90030-6 .PMID 6757811 . ^a b Nichols DE (2018).Chemistry and Structure-Activity Relationships of Psychedelics 1– 43.doi :10.1007/7854_2017_475 .ISBN 978-3-662-55878-2 PMID 28401524 .One of the earliest modifications of the tryptamines to be studied for psychoactive effects was the N,N-diethyl analogue of psilocin (CZ-74, 16). Both CZ-74 and its O-phosphoryl derivative CEY 19 (17) were studied in humans. Qualitatively, these compounds were very similar to psilocin and psilocybin, respectively, but had somewhat reduced durations of action (Leuner and Baer 1965). ^ McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes".Neuropharmacology .29 (3):193– 198.doi :10.1016/0028-3908(90)90001-8 .PMID 2139186 . ^ Nichols DE (February 11, 1999)."Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" Synthesis .1999 (6):935– 938.doi :10.1055/s-1999-3490 .S2CID 32044725 . ^ Repke DB, Ferguson WJ, Bates DK (1977)."Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl] ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols" .Journal of Heterocyclic Chemistry .14 (1):71– 74.doi :10.1002/jhet.5570140113 ISSN 0022-152X . Retrieved16 October 2025 . ^ Repke DB, Ferguson WJ (1982)."Psilocin analogs. III. Synthesis of 5‐methoxy‐ and 5‐hydroxy‐1,2,3,4‐tetrahydro‐9 H ‐pyrido[3,4‐ b ]indoles" Journal of Heterocyclic Chemistry .19 (4):845– 848.doi :10.1002/jhet.5570190428 .ISSN 0022-152X . Retrieved16 October 2025 . ^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on psychoactive substances banned from the consumer market].Finlex (in Finnish). Finnish Ministry of Justice. 19 December 2014.^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" [Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods;](PDF) .Svensk författningssamling (Swedish Code of Statutes) (in Swedish). 6 October 2005. Archived fromthe original (PDF) on 26 June 2021. Retrieved6 September 2013 .^ "21 U.S. Code § 841 - Prohibited acts A" ,LII / Legal Information Institute , retrieved2016-08-02
Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others Cyclized Ergolines /lysergamides (e.g.,LSD )β-Carbolines andHarmala alkaloidsharmine ,harmaline ,6-methoxyharmalan )Iboga alkaloids18-MAC ,18-MC ,coronaridine ,ibogaine ,ibogamine ,ME-18-MC ,noribogaine ,tabernanthine ,voacangine )Ibogalogs (e.g.,ibogainalog )O -MethylnordehydrobufoteninePartial 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 )Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI) ,NEtPhOH-THPI )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF ,dimemebfe (5-MeO-BFE) ,mebfap )Benzothiophenes (e.g.,3-APBT )Indazolethylamines (e.g.,AL-38022A ,O -methyl-AL-34662Indenylethylamines (e.g.,C-DMT )Isotryptamines (e.g.,6-MeO-isoDMT ,Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g.,mefloquine )
Phenethylamines
Scalines 2C-x Others: 2C-B-AN 2C-DB 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) BOx BOB ,BOD ,BOH-2C-B )HOT-x HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs 2CD-2-ETO ,2CD-5-ETO ,2CE-5-ETO ,2CE-5iPrO ,2CT2-5-ETO ,ASR-2001 (2CB-5PrO) )3C-x DOx 4C-x Ψ-PEA MDxx FLY 25x-NB (NBOMes) 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 ,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 PEA-NDEPAs 25D-NM-NDEAOP ,DOB-NDEPA ,DOI-NDEPA ,DOM-NDEPA ,DOTFM-NDEPA ,M-NDEPA ,TMA-2-NDEPA )PMA (4-MA) TMAs TMA-3 ,TMA-4 ,TMA-5 )TOMSO ZDCM-04 Cyclized 1-Aminomethylindanes (e.g.,2CB-Ind ,jimscaline )2-Aminoindanes (e.g.,DOM-AI )3-Benzazepines (e.g.,lorcaserin )3-Phenylpiperidines (e.g.,LPH-5 ,LPH-48 )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )DMBMPP (juncosamine) Ergolines /lysergamides (e.g.,LSD )Glaucine Partial ergolines (e.g.,NDTDI ,DEIMDHPCA ,DEMPDHPCA ,DEMTMPDHPCA ,DEMNDHPCA )Phenylcyclopropylamines (e.g.,DMCPA ,TMT )Phenyloxazolamines (aminorexes ) (e.g.,2C-B-aminorex )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 )Z3517967757 ZC-B
Lysergamides 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 )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 )Quinazolinylethylamines (e.g.,RH-34 )Natural sources Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca andvinho de Jurema (e.g.,Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum 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.Periglandula ipomoeae Periglandula clandestina
5-HT1
5-HT1A
Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g.,etoperidone ,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione ,vilazodone ,vortioxetine )Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,lurasidone ,quetiapine ,ziprasidone )Azapirones (e.g.,buspirone ,eptapirone ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,methylergometrine (methylergonovine) ,methysergide ,pergolide )F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT ,5-MeO-DMT ,5-MT ,bufotenin ,DMT ,indorenate ,N-Me-5-HT ,psilocin ,psilocybin )TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Atypical antipsychotics (e.g.,iloperidone ,risperidone ,sertindole )AV965 Beta blockers (e.g.,alprenolol ,carteolol ,cyanopindolol ,iodocyanopindolol ,isamoltane ,oxprenolol ,penbutolol ,pindobind ,pindolol ,propranolol ,tertatolol )BMY-7378 CSP-2503 Dotarizine Ergolines (e.g.,metergoline )FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
5-HT1B
Agonists: Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB ,6-MAPB ,BK-5-MAPB ,BK-6-MAPB )Benzothiophenes (e.g.,5-MAPBT ,6-MAPBT ,BK-5-MAPBT )CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )mCPP Methylenedioxyphenethylamines (e.g.,MDMA ,methylone )PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LSD ,methysergide )GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan ,avitriptan ,donitriptan ,eletriptan ,frovatriptan ,naratriptan ,rizatriptan ,sumatriptan ,zolmitriptan )Tryptamines (e.g.,5-BT ,5-CT ,5-Et-DMT ,5-MT ,5-(nonyloxy)tryptamine ,DMT )
5-HT1E
5-HT1F
5-HT2
5-HT2A
Agonists: 25H/NB series (e.g.,25I-NBF ,25I-NBMD ,25I-NBOH ,25I-NBOMe ,25B-NBOMe ,25C-NBOMe ,25TFM-NBOMe ,2CBCB-NBOMe ,25CN-NBOH ,2CBFly-NBOMe )2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g.,DOB ,DOC ,DOI ,DOM )Efavirenz Ergolines (e.g.,1P-LSD ,ALD-52 ,bromocriptine ,cabergoline ,ergine (LSA) ,ergometrine (ergonovine) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,methylergometrine (methylergonovine) ,pergolide )Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,BZP ,quipazine ,TFMPP )Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g.,cyproheptadine ,hydroxyzine ,ketotifen ,perlapine )AMDA Atypical antipsychotics (e.g.,amperozide ,aripiprazole ,asenapine ,blonanserin ,brexpiprazole ,carpipramine ,clocapramine ,clorotepine ,clozapine ,fluperlapine ,gevotroline ,iloperidone ,lurasidone ,melperone ,mosapramine ,ocaperidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,zicronapine ,ziprasidone ,zotepine )Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline )Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,haloperidol ,loxapine ,perphenazine ,pimozide ,pipamperone ,prochlorperazine ,setoperone ,spiperone ,spiramide ,thioridazine ,thiothixene ,trifluoperazine )Volinanserin Xylamidine Yohimbine
5-HT2B
Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g.,chlorphentermine ,cloforex ,dexfenfluramine ,fenfluramine ,levofenfluramine ,norfenfluramine )BW-723C86 DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,cabergoline ,dihydroergocryptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )Piperazines (e.g.,TFMPP )PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,α-Me-5-HT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: Agomelatine Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,N-desalkylquetiapine (norquetiapine) ,N-desmethylclozapine (norclozapine) ,olanzapine ,pipamperone ,quetiapine ,risperidone ,ziprasidone )Cyproheptadine EGIS-7625 Ergolines (e.g.,amesergide ,bromocriptine ,lisuride ,LY-53857 ,LY-272015 ,mesulergine )Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Trazodone Typical antipsychotics (e.g.,chlorpromazine )TIK-301 Yohimbine
5-HT2C
Agonists: 2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,ALD-52 ,cabergoline ,dihydroergotamine ,ergine (LSA) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,pergolide )Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,aripiprazole ,BZP ,mCPP ,quipazine ,TFMPP )PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin WAY-629 WAY-161503 YM-348 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,melperone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,ziprasidone ,zotepine )Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide ,bromocriptine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine ,pimozide ,pipamperone ,thioridazine )Xylamidine
5-HT3 –7
5-HT3
Agonists: Alcohols (e.g.,butanol ,ethanol (alcohol) ,trichloroethanol )m-CPBG Phenylbiguanide Piperazines (e.g.,BZP ,mCPP ,quipazine )RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g.,2-Me-5-HT ,5-CT ,bufotenidine (5-HTQ) )Volatiles/gases (e.g.,halothane ,isoflurane ,toluene ,trichloroethane )YM-31636 Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g.,clozapine ,olanzapine ,quetiapine )Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Thujone Tropanserin Tropisetron Typical antipsychotics (e.g.,loxapine )Volatiles/gases (e.g.,nitrous oxide ,sevoflurane ,xenon )Vortioxetine Zacopride Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g.,dihydroergocryptine ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,mesulergine ,metergoline ,methysergide )Hypidone Serotonin (5-HT) Tryptamines (e.g.,2-Me-5-HT ,5-BT ,5-CT ,5-MT ,Bufotenin ,E-6801 ,E-6837 ,EMD-386088 ,EMDT ,LY-586713 ,N-Me-5-HT ,ST-1936 ,tryptamine )WAY-181187 WAY-208466 Antagonists: ABT-354 Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,olanzapine ,tiospirone )AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,clorotepine ,clozapine ,fluperlapine ,olanzapine ,risperidone ,sertindole ,tiospirone ,ziprasidone ,zotepine )Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148) ,amesergide ,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,imipramine )Typical antipsychotics (e.g.,acetophenazine ,chlorpromazine ,chlorprothixene ,fluphenazine ,loxapine ,pimozide )Vortioxetine
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
Others: Antihistamines (e.g.,brompheniramine ,chlorphenamine ,pheniramine ,tripelennamine )Antipsychotics (e.g.,loxapine ,ziprasidone )Arylcyclohexylamines (e.g.,ketamine ,phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g.,desmetramadol ,methadone ,pethidine (meperidine) ,tapentadol ,tramadol ,levorphanol )
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
Others: A-80426 Amoxapine Antihistamines (e.g.,brompheniramine ,chlorphenamine ,dimenhydrinate ,diphenhydramine ,mepyramine (pyrilamine) ,pheniramine ,tripelennamine )Antipsychotics (e.g.,loxapine ,ziprasidone )Arylcyclohexylamines (e.g.,3-MeO-PCP ,esketamine ,ketamine ,methoxetamine ,phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g.,dextropropoxyphene ,methadone ,pethidine (meperidine) ,levorphanol ,tapentadol ,tramadol )Roxindole
VMATs Tooltip Vesicular monoamine transporters Others
Tryptamines 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-NiPT 5-HO-DPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS;O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O -methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ;N ,N ,N -TMS) Bufotenin (5-HO-DMT;N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 Cyclized tryptamines 5-MeO-IsoqT Barettin Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD )Harmala alkaloidsβ-carbolines (e.g.,5-methoxyharmalan ,6-MeO-THH ,6-methoxyharmalan ,9-Me-BC ,β-carboline (norharman) ,fenharmane ,harmaline ,harmalol ,harmane ,harmine ,LY-266,097 ,pinoline ,tetrahydroharmine ,tryptoline )Iboga alkaloidsibogaine ,ibogamine ,noribogaine ,tabernanthine )Ibogalogs (e.g.,catharanthalog ,fluorogainalog ,ibogainalog ,ibogaminalog (DM-506) ,LS-22925 ,noribogainalog ,noribogaminalog ,PHA-57378 ,PNU-22394 ,tabernanthalog )Imidazolylindoles (e.g.,AGH-107 ,AGH-192 ,AH-494 )Metralindole Morpholinylethylindoles (e.g.,mor-T ,5-MeO-mor-T )Partial ergolines and lysergamides (e.g.,NDTDI ,RU-27849 ,RU-28251 ,RU-28306 ,FHATHBIN ,LY-178210 ,Bay R 1531 (LY-197206) ,LY-293284 ,10,11-seco-LSD ,10,11-secoergoline (α,N -Pip-T) ,CT-5252 )Pertines (e.g.,alpertine ,milipertine ,oxypertine ,solypertine )Piperidinylethylindoles (e.g.,pip-T ,5-MeO-pip-T ,indolylethylfentanyl )Pyrrolidinylethylindoles (e.g.,pyr-T ,4-HO-pyr-T ,5-MeO-pyr-T ,4-F-5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g.,MPMI ,4-HO-MPMI (lucigenol) ,5F-MPMI ,5-MeO-MPMI ,CP-122288 ,CP-135807 ,eletriptan )Tetrahydrocarbazolamines (e.g.,ciclindole ,flucindole ,frovatriptan ,LY-344864 ,ramatroban )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 ,NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g.,bufothionine ,O -methylnordehydrobufotenineYohimbans (e.g.,yohimbine ,rauwolscine ,spegatrine ,corynanthine ,ajmalicine ,reserpine ,deserpidine ,rescinnamine )Isotryptamines Related compounds 2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline ,alosetron ,gevotroline ,latrepirdine ,lurosetron ,mebhydrolin ,tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,5-MeO-DiBF ,BPAP ,3-F-BPAP ,dimemebfe ,mebfap ,oxa-noribogaine )Benzothiophenes (e.g.,3-APBT )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g.,HT ,DMHT )I-32 IAL IN-399 Indazolethylamines (e.g.,AL-34662 ,AL-38022A ,O -methyl-AL-34662VU6067416 ,YM-348 )Indenylethylamines (e.g.,C-DMT )Indolizinylethylamines (e.g.,TACT908 (2ZEDMA) ,1ZP2MA ,1Z2MAP1O )Indolylaminopropanes (e.g.,1-API ,2-API ,4-API ,5-API (5-IT; PAL-571) ,6-API (6-IT) ,7-API )Iprindole Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan ,LY-334370 ,naratriptan ) Ondansetron Oxazinopyridoindoles (e.g.,IHCH-8134 )Phenethylamines (e.g.,phenethylamine ,amphetamine )Piperidinylbenzimidazolines (e.g.,benperidol ,timiperone )Piperazinylbenzisothiazoles (e.g.,lurasidone ,perospirone ,tiospirone ,ziprasidone )Piperidinylbenzisoxazoles (e.g.,iloperidone ,milsaperidone ,ocaperidone ,paliperidone ,risperidone )Piperidinylindoles (e.g.,BRL-54443 ,LY-334370 ,naratriptan ,sertindole ,SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g.,droperidol )Pyridinylindoles (e.g.,tepirindole )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 ,IHCH-7079 ,IHCH-7086 ,lumateperone ,deulumateperone ,ITI-1549 )Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA) ,3-pyrrolylethylamine (3-NEA) ,3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g.,WAY-208466 )Quinolinylethylamines (e.g.,mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088 ,LY-367265 ,RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g.,(R )-69 (3IQ) ,(R )-70 ,CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
