Psychoactive drug
Pharmaceutical compound
6-APB , also known as6-(2-aminopropyl)benzofuran , is anentactogen of thephenethylamine ,amphetamine , andbenzofuran families.[ 1] [ 2] Benzofury " in media reports. It issimilar in structure toMDA , but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with abenzofuran ring. 6-APB is also the unsaturated benzofuran derivative of6-APDB . It may appear as a tan or brown grainy powder.[citation needed
While the drug never became particularly popular, it briefly entered the rave and underground clubbing scene in the UK before its sale and import were banned. It falls under the category ofresearch chemicals , sometimes called "legal highs" if uncontrolled. Because 6-APB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to its popularity.[citation needed
6-APB was first described in thescientific literature in 2000[ 3] [ 4] [ 5] [ 6] designer drug in 2010.[ 4] [ 5] [ 7]
6-APB is reported to produceentactogenic ,stimulant , and mildpsychedelic effects in humans.[ 4] [ 8]
Acutepsychosis has been associated with recreational use of 6-APB in combination with thesynthetic cannabinoid JWH-122 .[ 9]
Small clumps of 6-APB powder 6-APB acts as aserotonin–norepinephrine–dopamine releasing agent (SNDRA), withEC50 Tooltip half-maximal effective concentration values formonoamine release of 36 nM forserotonin , 14 nM fornorepinephrine , and 10 nM fordopamine in rat brainsynaptosomes .[ 3] [ 7] serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), withaffinities (Ki ) of 117 nM for thenorepinephrine transporter (NET), 150 nM for thedopamine transporter (DAT), and 2,698 nM for theserotonin transporter (SERT)[ 2] IC50 Tooltip half-maximal effective concentration values formonoamine reuptake inhibition of 930 nM for serotonin, 190 nM for norepinephrine, and 3,300 nM for dopamine.[ 7]
In addition to actions at themonoamine transporters , 6-APB is apotent high-efficacy partial agonist orfull agonist of theserotonin 5-HT2B receptor (Ki = 3.7 nM;EC50 Tooltip half-maximal effective concentration = 140 nM;Emax Tooltip maximal efficacy = 70%).[ 2] target than any other site.[ 10] MDMA , 6-APB shows 100-foldselectivity for the serotonin 5-HT2B receptor over the serotonin5-HT2A and5-HT2C receptors in terms of affinity.[ 10] [ 6] 2B receptor than the reference serotonin 5-HT2B receptor agonist,BW-723C86 , which is commonly used for research into the serotonin 5-HT2B receptor.[citation needed Although much more potent at the serotonin 5-HT2B receptor, 6-APB is also a partial agonist of the serotonin 5-HT2A receptor (EC50 = 5,900 nM; Emax = 43%) and shows affinity for the serotonin 5-HT2C receptor (Ki = 270 nM) and the serotonin 5-HT1A receptor (Ki = 1,500 nM).[ 7] 2C receptor similarly to the serotonin 5-HT2A and 5-HT2B receptors.[ 4] [ 11]
Besides the serotonin 5-HT2 receptors, 6-APB has been found to bind with high affinity to theα2C -adrenergic receptor (Ki = 45 nM), although the significance of this action in humans is unknown.[ 2] trace amine-associated receptor 1 (TAAR1).[ 2] [ 7]
The potent agonism of the serotonin 5-HT2B receptor makes it likely that 6-APB would becardiotoxic with chronic or long-term use, as seen with other serotonin 5-HT2B receptor agonists such as thewithdrawn serotonergic anorectic fenfluramine .[ 2] [ 12]
Thepharmacokinetics of 6-APB have not been studied, however, some information can be extracted from user reports.[ 4] minutes.[ 4] hours, followed by a comedown phase of approximately 2 hours, and after effects for up to 24 hours.[ 4]
Although limited literature is available, there is some data onmetabolism of 6-APB in rats. Its Phase I metabolism involveshydroxylation of thefuran ring, then cleavage of the ring, followed by areduction of the unsaturatedaldehyde from the previous step. The resulting aldehyde may then take two paths. It is either oxidized to acarboxylic acid or reduced to analcohol , and thenhydroxylated . Phase II metabolism consists ofglucuronidation . The most prevalent metabolites in rats were3-carboxymethyl-4-hydroxyamphetamine and4-carboxymethyl-3-hydroxyamphetamine .[ 13]
6-APB, also known as 6-(2-aminopropyl)benzofuran, is aphenethylamine ,amphetamine , andbenzofuran and ananalogue of3,4-methylenedioxyamphetamine (MDA).
Synthesis of 6-APB and its structural isomer 4-APB[ 14] Thechemical synthesis of 6-APB has been described.[ 6] [ 6] 3-bromophenol with bromoacetaldehyde diethylacetal andsodium hydride to give the diethylacetal , which then was heated withpolyphosphoric acid to give a mixture of bromobenzofuranstructural isomers : 4-bromo-1-benzofuran and 6-bromo-1-benzofuran. The isomers were separated bysilica gel column chromatography , then converted to their respective propanone derivatives, and then reductively aminated to give 6-APB and 4-APB, both of which were converted to theirHCl ion pairs for further examination.
6-APB and its structural isomer5-APB have been tested with a series of agents including:Marquis ,Liebermann ,Mecke , andFroehde reagents.[ 15]
Compound Marquis Mecke Mandelin Liebermann Froehde Gallic Ehrlich Hofmann Simon's Folin 6-APB Purple Purple to black Purple to black Black Purple Brown Orange Light orange No reaction Light orange 6-APB succinate Purple Purple to black Purple to black Black Purple Brown Faint orange No reaction No reaction Light orange
6-APB succinate is reported to be practically insoluble inCHCl3 as well as very minimally soluble in coldwater . A batch seized by the DEA contained a 2:1 ratio of succinate to 6-APB.[ 14]
Analogues of 6-APB includeMDA ,6-APDB ,6-MAPB ,5-APB ,6-APBT , and6-API , among others.
6-APB, along with5-APB , was first described in thescientific literature by Karin Briner and colleagues atEli Lilly and Company in apatent in 2000.[ 3] [ 4] [ 5] [ 6] serotonin 5-HT2C receptor agonists for potential medical applications at this time.[ 3] [ 4] [ 5] [ 6] 5-APDB and6-APDB asserotonin releasing agents andentactogens byDavid E. Nichols and colleagues atPurdue University in 1993.[ 5] [ 7] [ 16] designer drug in 2010.[ 4] [ 5] [ 7] [ 5]
Society and culture [ edit ] In 1999, amphetamines were changed fromSchedule III toSchedule I as a result of theSafe Streets Act . Some have speculated that 6-APB's structure qualifies it as a Schedule I drug as ananalog of MDA.[ 17] [unreliable source?
In 2014, a study funded by theCanadian Institutes of Health Research noted that 6-APB "may or may not be legal in Canada depending on how one interprets the current Act"[ 18] benzofuran structure does not make it a direct analogue ofamphetamine despite similarities in effects.
6-APB has been a controlled substance in China since 1 July 2024[ 19]
6-APB is scheduled in government decree on narcotic substances, preparations and plants and hence is illegal.[ 20]
6-APB is illegal inFrance .[ 21]
6-APB is illegal inGermany since the 17th of July, 2013, when it was added toAnlage II of theBetäubungsmittelgesetz .[citation needed
6-APB is illegal inItaly .[ 22]
InLuxembourg , 6-APB is not cited in the list of prohibited substances.[ 23]
6-APB, as well as multiple substances based on the phenylethamine structure, like most cathinones and amphetamines, are banned under theOpium Law since July 1st, 2025,[ 24] Netherlands . Since this is a structural ban instead of a direct one, later substances that differ slightly but use the same skeleton will also be preemptively banned.
New Zealand and Australia [ edit ] Certain countries contain a "substantially similar" catch-all clause in their drug law, such asNew Zealand andAustralia . This includes 6-APB as it is similar in chemical structure to the class A drugMDA , meaning 6-APB may be viewed as a controlled substance analogue in these jurisdictions.[ 25]
InSweden , as of 27 December 2009 6-APB is classified as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor Act on the Prohibition of Certain Goods Dangerous to Health ).[ 26]
It is also classified as a narcotic substance since 2020.[ 27]
On June 10, 2013 6-APB and a number of analogues were classified asTemporary Class Drugs in the UK following an ACMD recommendation.[ 12] [ 28] Class B ,Schedule 1 substances.[ 12] [ 29]
6-APB is not an explicitlycontrolled substance in theUnited States .[ 30] controlled substance under theFederal Analogue Act if intended for human consumption.[ 31]
^a b c Oeri HE (May 2021)."Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy" .J Psychopharmacol .35 (5):512– 536.doi :10.1177/0269881120920420 .PMC 8155739 PMID 32909493 . ^a b c d e f Iversen L, Gibbons S, Treble R, Setola V, Huang XP,Roth BL (January 2013)."Neurochemical profiles of some novel psychoactive substances" .European Journal of Pharmacology .700 (1– 3):147– 151.doi :10.1016/j.ejphar.2012.12.006 .PMC 3582025 PMID 23261499 . ^a b c d Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020)."The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats" .Psychopharmacology (Berl) .237 (12):3703– 3714.doi :10.1007/s00213-020-05648-z .PMC 7686291 PMID 32875347 .The synthetic preparation of both 5-APB and 6-APB was first published in 2000 as part of a research program designed for the development of selective 5-HT2C receptor agonists (Briner et al. 2000; Briner et al. 2006), and the preparation of other isomers was reported for forensic purposes a decade later (Casale and Hays 2012; Stanczuk et al. 2013). ^a b c d e f g h i j Greene SL (2013). "Benzofurans and Benzodifurans".Novel Psychoactive Substances 383– 392.doi :10.1016/b978-0-12-415816-0.00016-x .ISBN 978-0-12-415816-0 . Retrieved15 April 2025 .A patent granted to Eli Lilly and Company in 2006 classifies 5-APB and 6-APB as 5HT2C receptor agonists [15]. [...] Internet user reports of 5-APB and 6-APB date from late 2010 [13]. [...] [15] Briner K, Burkhart JP, Burkholder TM, et al. Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists. 7045545 (US patent). Published 2000-01-19, issued 2006-16-03. ^a b c d e f g Roque Bravo R, Carmo H, Carvalho F, Bastos ML, Dias da Silva D (August 2019). "Benzo fury: A new trend in the drug misuse scene".J Appl Toxicol .39 (8):1083– 1095.doi :10.1002/jat.3774 .PMID 30723925 .The first benzofurans appearing on the drug scene in 2010‐11, were 5‐(2‐aminopropyl) benzofuran (5‐APB) and 6‐(2‐aminopropyl) benzofuran (6‐APB). These compounds had been previously patented in 2006 as potential therapeutic drugs for eating disorders and seizures, due to their action as serotonergic agonists (Advisory Council on the Misuse of Drugs, 2013; Taschwer, Hofer, & Schmid, 2014). While these first two molecules are the subject of most published investigations, namely those concerning pharmacological aspects, other benzofuran analogues have also been marketed as "legal highs." Examples of such analogues are 5‐(2‐ aminopropyl)‐2,3‐dihydrobenzofuran (5‐APDB) and 6‐(2‐aminopropyl)‐ 2,3‐dihydrobenzofuran (6‐APDB), first synthesized in 1993, purportedly as non‐neurotoxic benzofuran analogues of 3,4‐methylenedioxyamphetamine (MDA) (Monte, Marona‐Lewicka, Cozzi, & Nichols, 1993). These drugs are often confused with 5‐APB and 6‐APB (Casale, 2012; Casale & Hays, 2011). ^a b c d e f US patent 7045545 , Briner K, Burkhart JP, Burkholder TP, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YC, Xu Y, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006, assigned to Eli Lilly Co. ^a b c d e f g Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015)."Pharmacological profile of novel psychoactive benzofurans" .British Journal of Pharmacology .172 (13):3412– 3425.doi :10.1111/bph.13128 .PMC 4500375 PMID 25765500 .[5-APB] and [6-APB] are benzofuran analogues of MDA (Figure 1). [5-APDB] and [6-APDB] are dihydrobenzofuran analogues (Figure 1) that were originally synthesized for research purposes (Monte et al., 1993). [...] 5-APB and 6-APB appeared on the drug market in 2010– 2011 (Chan et al., 2013; Jebadurai et al., 2013; Stanczuk et al., 2013; Archer et al., 2014; Elliott and Evans, 2014; King, 2014), with reports of intoxication (Chan et al., 2013; Greene, 2013; Jebadurai et al., 2013; Seetohul and Pounder, 2013). ^ Canal CE (2018). "Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action".New Psychoactive Substances . Handbook of Experimental Pharmacology. Vol. 252. Cham: Springer International Publishing. pp. 227– 260.doi :10.1007/164_2018_107 ISBN 978-3-030-10560-0 PMC 6136989 PMID 29532180 .Despite micromolar 5-HT1A affinities (Rickli et al. 2015b), Nbenzylphenethylamines retain potent psychedelic effects. Also, benzofurans, such as 5-APB and 6-APB, are potent and efficacious 5-HT2B agonists but have very low potency at 5-HT2A receptors. They also stimulate efflux of DA and 5-HT and have activity at TAAR1 receptors (Iversen et al. 2013; Rickli et al. 2015a), but anecdotal reports note that psychedelic effects are relatively minor compared to classic psychedelics. These observations provide further credence that the 5-HT2A receptor, but not 5-HT1A, 5-HT2B, TAAR1, or monoamine transporters, initiates psychedelic effects. ^ Chan WL, Wood DM, Hudson S, Dargan PI (September 2013)."Acute psychosis associated with recreational use of benzofuran 6-(2-aminopropyl)benzofuran (6-APB) and cannabis" .Journal of Medical Toxicology .9 (3):278– 81.doi :10.1007/s13181-013-0306-y .PMC 3770991 PMID 23733714 . ^a b Canal CE, Murnane KS (January 2017)."2C receptor and the non-addictive nature of classic hallucinogens" .Journal of Psychopharmacology .31 (1):127– 143.doi :10.1177/0269881116677104 .PMC 5445387 PMID 27903793 . ^ US patent 7045545 , Karin Briner et al, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 2000-01-19, issued 2006-16-03 ^a b c Browne J (4 June 2013)."Temporary class drug order on benzofury and NBOMe compounds - letter from ACMD" .Advisory Council on the Misuse of Drugs . GOV.UK. ^ Nugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L (December 2015). "Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans".Drug and Alcohol Dependence .157 :18– 27.doi :10.1016/j.drugalcdep.2015.10.011 .PMID 26530501 . ^a b Casale JF, Hays PA (January 2012)."The Characterization of 6-(2-Aminopropyl)benzofuran and Differentiation from its 4-, 5-, and 7-Positional Analogues" (PDF) .Microgram Journal .9 (2):61– 74. Archived fromthe original (PDF) on 2016-11-05. Retrieved2016-06-08 . ^ "Results" .PRO Test . Retrieved2021-06-01 .^ Luethi D, Liechti ME (April 2020)."Designer drugs: mechanism of action and adverse effects" .Arch Toxicol .94 (4):1085– 1133.doi :10.1007/s00204-020-02693-7 .PMC 7225206 PMID 32249347 .Some benzofuran designer drugs were originally investigated as part of a study that examined the role of ring oxygen atoms in interactions between MDA and monoamine transporters (Monte et al. 1993). ^ "Controlled Drugs and Substances Act: Definitions and Interpretations" .isomerdesign.com . Retrieved2019-11-11 .^ Hudson AL, Lalies MD, Baker GB, Wells K, Aitchison KJ (2014-04-16)."Ecstasy, legal highs and designer drug use: A Canadian perspective" .Drug Science, Policy and Law 1 2050324513509190.doi :10.1177/2050324513509190 ISSN 2050-3245 .S2CID 159675835 . ^ National Medical Products Administration (NMPA) of China (July 22, 2024)."关于将溴啡等46种物质列入《非药用类麻醉药品和精神药品管制品种增补目录》的公告" . ^ "Ajantasa" .finlex.fi .^ "Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" .^ "Nuove tabelle delle sostanze stupefacenti e psicotrope (DPR 309/90)" (PDF) (in Italian). Ministero della Salute. Archived fromthe original (PDF) on 2016-02-06. Retrieved2016-05-31 .^ "Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie. - Legilux" .legilux.public.lu . Retrieved2021-06-01 .^ "Lijst verboden Nieuwe Psychoactieve Stoffen (NPS) per 1 juli 2025" .www.rijksoverheid.nl . July 2025. Retrieved2025-07-10 .^ "Misuse of Drugs Act 1975" . New Zealand Legislation. 7 November 2015.^ "Förordning (1999:58) om förbud mot vissa hälsofarliga varor" (in Swedish). Lagbevakning med Notisum och Rättsnätet. 24 November 2009. Archived fromthe original on 4 October 2013. Retrieved15 September 2013 .^ "Förordning (1992:1554) om kontroll av narkotika" .www.riksdagen.se (in Swedish). Retrieved2025-07-14 .^ Browne J (4 June 2013)." .Home Office . GOV.UK. ^ UK Home Office (28 April 2014)."The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" . The National Archives. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF) ,United States : U.S.Department of Justice :Drug Enforcement Administration (DEA): Diversion Control Division, January 2026^ Casale JF, Hays PA (January 2011)."The characterization of 5-and 6-(2-aminopropyl)-2, 3-dihydrobenzofuran" .Microgram J .8 (2):62– 74.
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
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
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
TAAR1 Tooltip Trace amine-associated receptor 1
TAAR5 Tooltip Trace amine-associated receptor 5
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the
List of trace amines ,
TAAR , and
TAAR1 pages.
See also: Receptor/signaling modulators
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,2C-B-3PIP ,2C-B-3PIP-NBOMe ,2C-B-3PIP-POMe ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )Phenylbutylamines (e.g.,4-Phenylbutylamine ,4-Phenylpentan-1-amine )
N
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