Chemical compound
Pharmaceutical compound
4-HO-DiPT , also known as4-hydroxy-N ,N -diisopropyltryptamine or asiprocin , is apsychedelic drug of thetryptamine and4-hydroxytryptamine families related topsilocin (4-HO-DMT).[ 1] [ 3] It is takenorally .[ 1] The drug has an unusually fastonset , shortduration , and narrow dose range.[ 1]
It acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A receptor .[ 4] [ 5] [ 6] [ 7] Unlike many other psychedelic tryptamines, the drug appears to have far lowerpotency as an agonist of the serotonin5-HT2C receptor relative to the serotonin 5-HT2A receptor.[ 4] [ 5] [ 6] [ 7] It is aderivative ofDiPT , a higherhomologue of psilocin (4-HO-DMT) and4-HO-DET , and askeletal isomer of4-HO-DPT .[ 1]
4-HO-DiPT was first described in thescientific literature by 1977.[ 3] [ 8] [ 9] It was later described in greater detail byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved ).[ 3] [ 8] [ 1] The drug was encountered as a noveldesigner drug by 2005.[ 10] In the 2020s, aprodrug of 4-HO-DiPT known asluvesilocin (RE-104, FT-104; 4-GO-DiPT) was developed and is inclinical trials for the treatment ofpsychiatric disorders such aspostpartum depression .[ 3] [ 11] [ 12] [ 2]
In his bookTiHKAL (Tryptamines I Have Known and Loved ) and other publications,Alexander Shulgin reported that 4-HO-DiPT had adose range of 15 to 20 mgorally and aduration of 2 to 3 hours.[ 1] [ 13] [ 14] However, a wider dose range of 3 to 30 mg or more orally has also been reported.[ 15] Shulgin has stated that 4-HO-DiPT has an especially steepdose–response curve and narrow dose range, with doses below 10 mg producing few to no effects and doses of more than 20 mg having not been tested due to the intensity of its effects.[ 1] He personally found that a 20 mg dose produced an intense plus-three experience on theShulgin Rating Scale that "flirted with" the magical plus-four transcendental peak experience.[ 1] The drug'sonset of action is 15 to 20 minutes and peak effects occur after 20 to 30 minutes.[ 1] Shulgin has stated that he "truly doubt[s] that there is another psychedelic drug, anywhere, that can match [4-HO-DiPT] for speed, for intensity, for brevity, and [sensitivity] to dose, at least one that is active orally."[ 1]
The effects of 4-HO-DiPT have been reported to includeintrospective changes,insights and realizations, mild object distortion, slight color effects, rainbow halos around objects, very little in the way ofclosed-eye visuals , little in terms ofpsychedelic visuals orsensory changes in general, mildstimulation , mildelation , lighttension ,orgasmic enhancement, and powerfulreligious-esque experiences .[ 1] Other effects included sensations ofmuscle loosening , legtremors ,chill -like sensations, and vague bodymalaise .[ 1] Shulgin has stated that he doubts that 4-HO-DiPT could be distinguished frompsilocin (4-HO-DMT) in anyblinded clinical study .[ 16] Due to its rapid onset and short duration among other qualities, 4-HO-DiPT has been described as a "good 'novice' introduction to hallucinogens".[ 1]
Luvesilocin (RE104; 4-GO-DiPT)Drug Effects Questionnaire (DEQ) "feel high" ratings at doses of 5 to 40 mg (equivalent to ~4–32 mg 4-HO-DiPT) viasubcutaneous injection over 6 hours.[ 2] The effects of 4-HO-DiPT have been clinically studied in the form of itsprodrug luvesilocin (RE-104; FT-104; 4-GO-DiPT).[ 2] Luvesilocin was evaluated at doses of 5 to 40 mg (equivalent to ~4–32 mg 4-HO-DiPT) bysubcutaneous injection in this study.[ 2] It was specifically assessed in terms of modifiedDrug Effects Questionnaire (DEQ) ratings, Mystical Experience Questionnaire (MEQ) ratings, andadverse effects .[ 2]
4-HO-DiPT activities Target Affinity (Ki , nM)5-HT1A 5,700–>10,000 (Ki ) 1,147–3,900 (EC50 Tooltip half-maximal effective concentration ) 36–70% (Emax Tooltip maximal efficacy ) 5-HT1B >10,000 (Ki ) 597–>10,000 (EC50 ) 95% ( Emax ) 5-HT1D 1,860 (Ki ) 496–8,827 (EC50 ) 64–124% ( Emax ) 5-HT1E >10,000 (Ki ) 852–>10,000 (EC50 ) 79% ( Emax ) 5-HT1F ND (Ki ) 557 ( EC50 ) <20–59% ( Emax ) 5-HT2A 120–922 (Ki ) 6.8–334a (EC50 ) 74–106% ( Emax ) 5-HT2B 85 (Ki ) 5.1–460 (EC50 ) 55–110% ( Emax ) 5-HT2C 2.8–>10,000 (Ki ) 180–6,442 (EC50 ) 72–104%a ( Emax ) 5-HT3 ND 5-HT4 ND (Ki ) >10,000 ( EC50 ) IA ( Emax ) 5-HT5A >10,000 (Ki ) 243–5,074 (EC50 ) 56–66% ( Emax ) 5-HT6 >10,000 (Ki ) 697–2,415 (EC50 ) 55–56% ( Emax ) 5-HT7 >10,000 (Ki )ND ( EC50 ) <20% ( Emax ) α1A >12,000 α1B ,α1D ND α2A 15,000 α2B ,α2C >10,000 β1 –β3 ND D1 –D3 >25,000 D4 ,D5 >10,000 H1 9,800–>10,000 H2 >10,000 H3 ,H4 ND M1 –M3 ND M4 1,725 M5 ND I1 ND σ1 816–1,063 σ2 2,215 KOR Tooltip κ-Opioid receptor >10,000 NR2B >10,000 TAAR1 Tooltip Trace amine-associated receptor 1 >15,000 (Ki ) (mouse) >15,000 (Ki ) (rat)ND ( EC50 ) (human) SERT Tooltip Serotonin transporter 419–1,800 (Ki ) 163–2,400 (IC50 Tooltip half-maximal inhibitory concentration )IA ( EC50 ) NET Tooltip Norepinephrine transporter 11,000 (Ki ) 46,000 (IC50 ) IA ( EC50 ) DAT Tooltip Dopamine transporter >26,000 (Ki ) >100,000 (IC50 ) IA ( EC50 ) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Footnotes: a = Stimulation ofIP1 Tooltip inositol phosphate formation.Refs: [ 4] [ 5] [ 6] [ 7] [ 17] [ 18] [ 19] [ 20]
4-HO-DiPT acts as anagonist ofserotonin receptors , including theserotonin 5-HT2A and5-HT2B receptors .[ 4] [ 5] [ 6] [ 7] [ 18] It may also act as aserotonin reuptake inhibitor , although itspotency is variable across studies.[ 4] [ 5] [ 6] [ 7] The drug appears to activate the serotonin5-HT2C receptor with low potency and much lower than for the serotonin 5-HT2A receptor.[ 4] [ 5] [ 6] [ 7] However, in another study, it was only about 2.5-fold more potent as an agonist of the serotonin 5-HT2A receptor relative to the serotonin 5-HT2C receptor.[ 19] The drug activates other serotonin receptors with lower potency as well.[ 19] Unlike many othertryptamines , 4-HO-DiPT is not aligand of the rodenttrace amine-associated receptor 1 (TAAR1).[ 4] [ 20]
The drug has been found to produce thehead-twitch response , a behavioral proxy of psychedelic effects, in rodents.[ 3] [ 14] [ 5] In addition, it has fully efficaciousanti-inflammatory effects inpreclinical research .[ 3] [ 18] 4-HO-DiPT has also been found to produceanxiolytic effects in rodents.[ 19]
Thepharmacokinetics of 4-HO-DiPT have been studied.[ 17] [ 2] Theelimination half-life of 4-HO-DiPT in humans when given in the form of itsprodrug luvesilocin (4-GO-DiPT) bysubcutaneous injection has been found to range from 2.7 to 4.1 hours.[ 2] The average experienceduration was 3.6 hours at a dose of 30 mg in the study.[ 2]
4-HO-DiPT, also known as 4-hydroxy-N ,N -diisopropyltryptamine, is asubstituted tryptamine .[ 1] It is asynthetic analogue of theneurotransmitter serotonin (5-hydroxytryptamine; 5-HT) and of thenaturally occurring serotonergic psychedelics psilocin (4-HO-DMT) andpsilocybin (4-PO-DMT).[ 1] [ 3]
Thechemical synthesis of 4-HO-DiPT has been described.[ 1]
4-HO-DiPT is closely related toanalogues includingdiisopropyltryptamine (DiPT),5-MeO-DiPT ,psilocin (4-HO-DMT),4-HO-DET (ethocin),4-HO-MET (metocin),4-HO-MiPT (miprocin),4-HO-DPT (deprocin),4-HO-MPT (meprocin),4-HO-DALT (dalocin),4-HO-MALT (malocin), and5-HO-DiPT , among others.[ 1] 4-AcO-DiPT (ipracetin),4-PrO-DiPT , andluvesilocin (4-GO-DiPT) areester prodrugs of 4-HO-DiPT.[ 3] [ 5] [ 2]
4-HO-DiPT was first described in thescientific literature byDavid Repke and colleagues in 1977.[ 3] [ 8] [ 9] Subsequently, its effects in humans were described byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved ).[ 3] [ 8] [ 1] The drug was encountered as a noveldesigner drug inEurope by 2005.[ 10] Luvesilocin (4-GO-DiPT), aprodrug of 4-HO-DiPT, was first described in 2021.[ 3] [ 21]
Society and culture [ edit ] 4-HO-DiPT powder. Scheduled in government decree on psychoactive substances banned from the consumer market.[ 22]
Scheduled in New Psychoactive Substances Act (NpSG ). Use of covered substances is permitted only for industrial and scientific purposes.
Sveriges riksdags health ministryStatens folkhälsoinstitut classified 4-HO-DiPT as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct on the Prohibition of Certain Goods Dangerous to Health ) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 4-hydroxi-N,N-diisopropyltryptamin (4-HO-DIPT), making it illegal to sell or possess.[ 23]
4-HO-DiPT is not scheduled at the federal level in theUnited States ,[ 24] but it is possible that it could be considered an analog of5-MeO-DiPT , in which case purchase, sale, or possession could be prosecuted under theFederal Analog Act . The United StatesDrug Enforcement Administration (DEA) proposed scheduling 4-HO-DiPT in January 2022, but due to an effective public response, it withdrew its proposal in July 2022.[ 3]
"4-Hydroxy-N,N-diisopropyltryptamine" is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.[ 25]
Luvesilocin (RE-104, FT-104; 4-GO-DiPT), aprodrug of 4-HO-DiPT.Luvesilocin (developmental code names RE-104, FT-104;O -glutaryl-4-HO-DiPT or 4-GO-DiPT), aprodrug of 4-HO-DiPT, has enteredphase 2 clinical trials for treatment ofpsychiatric conditions such aspostpartum depression andtreatment-resistant depression .[ 11] [ 26] [ 27] [ 28]
^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 .https://www.erowid.org/library/books_online/tihkal/tihkal17.shtml ^a b c d e f g h i j Ludbrook G, Bryson N, Taylor B, Hocevar-Trnka J, Johnson MW, Hirman J, et al. (2025)."Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study" .J Clin Psychopharmacol .45 (5):441– 453.doi :10.1097/JCP.0000000000002047 .PMC 12379775 .PMID 40685873 . ^a b c d e f g h i j k l "4-HO-DiPT" .Psychedelic Science Review . 23 June 2022. Retrieved8 October 2025 .^a b c d e f g Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016)."Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF) .Eur Neuropsychopharmacol .26 (8):1327– 1337.doi :10.1016/j.euroneuro.2016.05.001 .PMID 27216487 . ^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 Pharmacol Transl Sci .4 (2):533– 542.doi :10.1021/acsptsci.0c00176 .PMC 8033608 .PMID 33860183 . ^a b c d e f 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-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter" .J Pharmacol Exp Ther .385 (1):62– 75.doi :10.1124/jpet.122.001454 .PMC 10029822 .PMID 36669875 . ^a b c d e f Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, et al. (April 2023)."Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice" .ACS Pharmacol Transl Sci .6 (4):567– 577.doi :10.1021/acsptsci.2c00222 .PMC 10111620 .PMID 37082754 . ^a b c d Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, et al. (2018)."The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines" .Front Integr Neurosci .12 54.doi :10.3389/fnint.2018.00054 .PMC 6235949 .PMID 30467466 .4-OH-DiPT (4-Hydroxy-diisopropyltryptamine): substituted tryptamine, first synthesized by Repke et al. (1977) and investigated in humans by A. Shulgin (Shulgin and Shulgin, 1997). ^a b 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 . ^a b https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005 ^a b "RE 104" .AdisInsight . 23 September 2025. Retrieved8 October 2025 .^ Bryson N, Alexander R, Asnis-Alibozek A, Ehlers MD (June 2024)."RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine" .ACS Chem Neurosci .15 (12):2386– 2395.doi :10.1021/acschemneuro.4c00058 .PMC 11191588 .PMID 38758589 . ^ Shulgin AT (2003)."Basic Pharmacology and Effects" . In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook . Forensic Drug Handbook Series. Elsevier Science. pp. 67– 137.ISBN 978-0-12-433951-4 . ^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. [...] ^ Luethi D, Liechti ME (October 2018)."Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics" .Int J Neuropsychopharmacol .21 (10):926– 931.doi :10.1093/ijnp/pyy047 .PMC 6165951 .PMID 29850881 . ^ Shulgin A, Shulgin A (September 1997)."#21. 4-HO-MET" .Isomer Design . Transform Press. Retrieved28 November 2023 .With [4-HO-MET], some of the original observations suggested that it was more potent than psilocin, certainly more dramatic. But at the bottom line, I doubt that this ethyl homologue, or the isopropyl homologue 4-HO-DIPT for that matter, could be distinguished from the methyl counterpart psilocin in any blind clinical study. ^a b Bryson N, Alexander R, Asnis-Alibozek A, Ehlers MD (June 2024)."RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine" .ACS Chem Neurosci .15 (12):2386– 2395.doi :10.1021/acschemneuro.4c00058 .PMC 11191588 .PMID 38758589 . ^a b c Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021)."Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore" .ACS Pharmacol Transl Sci .4 (2):488– 502.doi :10.1021/acsptsci.0c00063 .PMC 8033619 .PMID 33860179 . ^a b c d Kelly TJ, Bonniwell EM, Mu L, Liu X, Hu Y, Friedman V, et al. (April 2024)."Psilocybin analog 4-OH-DiPT enhances fear extinction and GABAergic inhibition of principal neurons in the basolateral amygdala" .Neuropsychopharmacology .49 (5):854– 863.doi :10.1038/s41386-023-01744-8 .PMC 10948882 .PMID 37752222 . ^a b Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016)."In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF) .J Pharmacol Exp Ther .357 (1):134– 144.doi :10.1124/jpet.115.229765 .PMID 26791601 . Archived fromthe original (PDF) on 9 May 2025. ^ Bryson N. Tryptamine prodrugs. US 2021/0403425 A1, Field Trip Psychedelics, Inc0. Published online April 5, 2022. Accessed May 27, 2022.https://patents.google.com/patent/US11292765B2/en?q=field+trip+health&assignee=Field+Trip+Psychedelics+Inc . ^ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014" .www.finlex.fi . Retrieved8 April 2023 .^ "Svensk författningssamling" [Swedish Code of Statutes](PDF) (in Swedish). Archived fromthe original (PDF) on 29 September 2013. Retrieved25 September 2013 .^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived fromthe original on 27 August 2009. Retrieved17 December 2014 .^ "Statutes & Constitution :View Statutes : Online Sunshine" .leg.state.fl.us . Retrieved8 April 2023 .^ "Field Trip Announces First Dosings in Phase I Clinical Study of FT-104" (Press release). 21 July 2022.^ "An Inside Look into Field Trip's Next-Generation Psychedelic, FT-104" . 11 August 2022.^ "WIPO - Search International and National Patent Collections" .patentscope.wipo.int . Retrieved8 April 2023 .
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 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 -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-34662 )Indenylethylamines (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 (e.g.,BOB ,BOD ,BOH-2C-B )HOT-x (e.g.,HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs (e.g.,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 (e.g.,25D-NM-NDEAOP ,DOB-NDEPA ,DOI-NDEPA ,DOM-NDEPA ,DOTFM-NDEPA ,M-NDEPA ,TMA-2-NDEPA )PMA (4-MA) TMAs (e.g.,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. (e.g.,Acacia acuminata ,Acacia confusa )Ayahuasca andvinho 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 )
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 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 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-T 6,7-DHT 7-Chloro-T 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 MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-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 andesters /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-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 alkaloids andβ-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 alkaloids (e.g.,ibogaine ,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 -methylnordehydrobufotenine )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 ,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-34662 ,VU6067416 ,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)