Psychedelic drug
"Miprocin" redirects here; not to be confused with
Mupirocin .
Pharmaceutical compound
4-HO-MiPT , also known as4-hydroxy-N -methyl-N -isopropyltryptamine or asmiprocin , is apsychedelic drug of thetryptamine and4-hydroxytryptamine families related topsilocin (4-HO-DMT).[ 1] [ 3] [ 4] onset ,duration , and effects.[ 1] [ 3] [ 4] orally .[ 1] [ 3] [ 4]
It acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A receptor among others.[ 3] [ 5] structurally toMiPT ,4-HO-DiPT , andpsilocin (4-HO-DMT).[ 1]
4-HO-MiPT was first described in the literature byDavid Repke and colleagues in 1981.[ 6] [ 7] [ 3] [ 8] Alexander Shulgin in 1985[ 4] [ 1] [ 3]
According toAlexander Shulgin in his bookTiHKAL Tryptamines I Have Known and Loved ) and other publications, 4-HO-MiPT has a dose range of 12 to 25 mg, anonset of action of 10 to 20 minutes, a time to peak of 40 to 45 minutes, and aduration of 4 to 6 hours.[ 1] [ 3] [ 4] [ 9] mg.[ 9] potent aspsilocin (4-HO-DMT) at comparable doses, with 20 mg 4-HO-MiPT being subjectively stronger than 50 mg psilocin in one individual.[ 1] [ 3] 4-AcO-MiPT (aprodrug of 4-HO-MiPT) at a dose of 30 mg were described as considerably more modest than expected.[ 1]
The effects of 4-HO-MiPT have been reported to includeclosed-eye visuals , vividmental imagery , fewpsychedelic visuals , wave-form visuals, intense color alterations, multiple images of the same object with intense colored halos, illusory alteration of the size and distance of objects, heightening ofsenses , intensification and enhanced discrimination of sounds, increased sense of bodily processes such as blood flow and muscles,synesthesia of sound and sight, intense alteration in sense of time and distance, feelings of drifting in and out of the body, flight of ideas,philosophical thinking,euphoria , enhancedmusic appreciation, enhancederoticism , and facilitation oflove ,insights ,fantasy ,introspection , anddiscovery .[ 1] [ 3] [ 4] intoxication ,sedation ,feeling drunk ,relaxation , some initialanxiety , easy to difficult verbalcommunication , easydistraction andannoyance by externalstimuli such aslight ,appetite loss , andinsomnia .[ 1] [ 3] [ 4] twitching , muscle sensations,motor incoordination , slightlightheadedness , mildvertigo ,jaw clenching , and bodytremors .[ 1] [ 4]
4-HO-MiPT acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A ,5-HT2B , and5-HT2C receptors .[ 3] [ 5] [ 10] [ 11] potency andefficacy as an agonist of the 5-HT2A receptor, moderate potency as apartial agonist of the 5-HT2B receptor, and low potency with high-efficacy as a partial agonist of the 5-HT2C receptor.[ 5] [ 11] serotonin transporter (SERT)blocker orserotonin reuptake inhibitor .[ 10] 5-HT1A receptor suggest minimal contribution to this drug's effects.[ 11] selectivity for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor, and 4-fold preference relative to SERT inhibition.[ 5] [ 10] [ 11] receptors outside of theserotonin receptor family have not yet been assessed.[ 5] [ 11]
The drug induces thehead-twitch response , a behavioral proxy of psychedelic effects, in rodents.[ 5] [ 9] psilocin .[ 5]
4-HO-MiPT, also known as 4-hydroxy-N -methyl-N -isopropyltryptamine, is asynthetic derivative of thesubstituted tryptamine and4-hydroxytryptamine families.[ 1] hydroxy analogue ofN -methyl-N -isopropyltryptamineN -isopropyl homologue of psilocin (4-HO-DMT).[ 1]
4-HO-MiPT appears to be a relativelyunstable compound, discoloring quickly if not kept in an inert atmosphere and in a freezer.[ 1] [ 3] prodrug analogue 4-AcO-MiPT have been used as thefree base ,hydrochloride salt , andfumarate salt.[ 1] [ 6] [ 7]
In August 2019, Chadeayne et al. solved thecrystal structure of 4-HO-MiPT fumarate.[ 3] [ 6] H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate.[ 6] [ 6]
Thechemical synthesis of 4-HO-MiPT has been described.[ 1] [ 8]
Analogues of 4-HO-MiPT includeN -methyl-N -isopropyltryptamine4-AcO-MiPT ,4-MeO-MiPT ,5-MeO-MiPT ,4-HO-DiPT ,psilocin (4-HO-DMT),4-HO-MET ,4-HO-EiBT , and4-HO-McPT , among others.[ 1]
4-HO-MiPT was first described in thescientific literature byDavid Repke and colleagues in 1981.[ 6] [ 7] [ 3] [ 8] Alexander Shulgin and colleagues in 1985.[ 6] [ 7] [ 4] pharmacology of 4-HO-MiPT atserotonin receptors was described byDennis McKenna and Repke and colleagues in 1990.[ 6] [ 12] TiHKAL Tryptamines I Have Known and Loved ).[ 1] [ 3]
Society and culture [ edit ] 4-HO-MiPT is not acontrolled substance inCanada as of 2025.[ 13]
4-HO-MiPT is in Schedule 1 inRussia as an analog of 4-hydroxytryptamine.[citation needed
Sveriges riksdags Statens folkhälsoinstitut classified 4-HO-MiPT as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor Act on the Prohibition of Certain Goods Dangerous to Health ) as of 1 November 2005, in regulation SFS 2005:733 listed as "4-hydroxi-N,N-metylisopropyltryptamin (4-HO-MIPT)", making it illegal to sell or possess.[ 14]
The substance could also be considered illegal in theUnited Kingdom under theMisuse of Drugs Act 1971 .[citation needed
4-HO-MiPT is an unscheduled drug in theUnited States . However, it is arguably ananalog of psilocin, which could lead to prosecution under theFederal Analog Act .[citation needed
^a b c d e f g h i j k l m n o p q r s t u Shulgin A ,Shulgin A (September 1997).TiHKAL: The Continuation Berkeley, California :Transform Press .ISBN 0-9630096-9-9 OCLC 38503252 .http://www.erowid.org/library/books_online/tihkal/tihkal22.shtml ^ Anvisa (24 July 2023)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 25 July 2023).Archived from the original on 27 August 2023. Retrieved27 August 2023 . ^a b c d e f g h i j k l m n o p Bauer BE (6 January 2020)."4-HO-MiPT" .Psychedelic Science Review . Retrieved9 October 2025 . ^a b c d e f g h i Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents".Journal of Medicinal Chemistry .28 (7):892– 896.doi :10.1021/jm00145a007 .PMID 4009612 . ^a b c d e f g h 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 . ^a b c d e f g h Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019)."The fumarate salts of theN -isopropyl-N -methyl derivatives of DMT and psilocin" .Acta Crystallographica Section E .75 (Pt 9):1316– 1320.Bibcode :2019AcCrE..75.1316C .doi :10.1107/S2056989019011253 PMC 6727059 PMID 31523457 .The synthesis of N-methyl-N-isopropyltryptamine (MiPT) was reported in 1981 (Repke et al., 1981). In 1985, Repke and co-workers reported that of the compounds in the series of N,N-dialkyl-4-hydroxytryptamines, the N-methyl-N-isopropyl derivative (4-HO-MiPT) is the most potent based upon qualitative effects on humans (Repke et al., 1985). Later quantitative studies showed the N-methyl-N-isopropyl derivatives of DMT and psilocin to be more potent as seratonin-1A, 2A and 2B receptors compared to the analogous dimethyl compounds (McKenna et al., 1990). ^a b c d Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020)."Bis(4-hy-droxy-N -isopropyl-N -methyl-trypt-ammo-nium) fumarate: a new crystalline form of miprocin" .Acta Crystallographica Section E .76 (Pt 4):514– 517.Bibcode :2020AcCrE..76..514C .doi :10.1107/S2056989020002923 PMC 7133045 PMID 32280495 .4-Hydroxy-N-methyl-N-isopropyltryptamine (4-HOMiPT), aka 'miprocin', is a psilocybin analogue. Its synthesis was first reported in 1981 by Repke and co-workers (Repke et al., 1981); its psychedelic effects were later described in collaboration with Alexander Shulgin (Repke et al., 1985). Miprocin is reported to produce an experience that is both relaxing, stoning and mildly sedating with a marked physical stimulation that distinguishes it from related substances such as psilocybin mushrooms. In a report last year, we presented the first structure of 4-HO-MiPT (Chadeayne, Pham et al., 2019a), which crystallizes as the hydrofumarate monohydrate. Herein we report the reaction of this salt with lead(II) acetate to generate the 4-hydroxy-N-isopropyl-N-methyltryptaminium/fumarate compound in a 2:1 ratio. The solid state structure of the new salt is presented here. ^a b c Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols".Journal of Heterocyclic Chemistry .18 (1):175– 179.doi :10.1002/jhet.5570180131 .ISSN 0022-152X . ^a b c 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" .Neuropharmacology .167 107933.doi :10.1016/j.neuropharm.2019.107933 .PMC 9191653 PMID 31917152 .Table 4 Human potency data for selected hallucinogens. [...] ^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 Glatfelter G, Walther D, Partilla J, Chadeayne AR, Manke DR, Baumann MH (1 June 2024)."Pharmacological profiles and psychedelic-like effects of 4-hydroxy-, 4-acetoxy-, and 4-methoxy-N- methyl- N- isopropyltryptamine" The Journal of Pharmacology and Experimental Therapeutics .389 : 281.doi :10.1124/jpet.281.923160 .ISSN 0022-3565 . ^ 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 . ^ "Controlled Drugs and Substances Act" .Department of Justice Canada . Retrieved19 January 2026 .^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" [Regulation amending the Ordinance (1999: 58) on Prohibition against certain dangerous goods](PDF) .Swedish Code of Statutes (in Swedish). 6 October 2005. Archived fromthe original (PDF) on 26 June 2021. Retrieved6 September 2013 .
Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others Cyclized Ergolines /lysergamides (e.g.,LSD )Ibogalogs (e.g.,ibogainalog ,tabernanthalog )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 ,MSP-2020 )Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI) ,NEtPhOH-THPI )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF (1-oxa-5-MeO-DiPT) ,dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) ,mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) )Benzothiophenes (e.g.,3-APBT (1-thia-AMT) )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 ,BOHB )HOT-x HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs 2CB-2-EtO ,2CD-2-EtO ,2CD-5-EtO ,2CE-5-EtO ,2CE-5iPrO ,2CT2-5-EtO ,ASR-2001 (2CB-5-PrO) )3C-x DOx 4C-x Ψ-PEA MDxx FLY 25x-NB (NBOMes) Others 25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM 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) Thio-2Cs (e.g.,2C-5-TOET )Thio-DOx (e.g.,2-TOM ,5-TOET ,5-TOM ,TOMSO )TMAs TMA-3 ,TMA-4 ,TMA-5 )ZDCM-04 (DOC-fenethylline) 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 (F-11440) ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol (NLX-112; F-13640) 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 (NLX-101) Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) 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: Alniditan 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-12066 (CGS-12066A, CGS-12066B) 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 )PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,IS-159 ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) 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 ,IS-159 ,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 )Butanserin 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 LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )Temanogrel Teniloxazine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TGBA01AD Trelanserin 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 ATHX-105 Centhaquine 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 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin VR-1065 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 FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin 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 1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 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-DPT 5-HO-MET 5-HO-NiPT 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-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O -methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-NOT 5-PhO-T (OVT2) 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) IS-159 Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)NB-5-MeO-DALT NB-5-MeO-MiPT 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 α-Ketotryptamines Cyclized tryptamines 5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) 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 ,L-760790 )Pyrrolidinylmethylindoles (e.g.,MPMI ,4-HO-MPMI (lucigenol) ,5F-MPMI ,5-MeO-MPMI ,CP-122288 ,CP-135807 ,eletriptan ,MSP-2020 )Tetrahydrocarbazolamines (e.g.,ciclindole ,flucindole ,frovatriptan ,LY-344864 ,ramatroban )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 ,NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g.,bufothionine ,O -methylnordehydrobufoteninedehydrobufotenine )Yohimbans (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 (1-oxa-AMT) ,5-MeO-DiBF (1-oxa-5-MeO-DiPT) ,BPAP ,3-F-BPAP ,dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) ,mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) ,MiPBF (1-oxa-MiPT) ,oxa-noribogaine )Benzothiophenes (e.g.,S-DMT (1-thia-DMT) ,3-APBT (1-thia-AMT) )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 (1-carba-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-93129 ,CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
