Psychedelic phenthylamine drug
Pharmaceutical compound
2C-T-7 , also known as4-propylthio-2,5-dimethoxyphenethylamine or asBlue Mystic or7th Heaven , is apsychedelic drug of thephenethylamine and2C families.[ 1] [ 2] [ 3] [ 4] It is takenorally .[ 1]
2C-T-7 was first described in thescientific literature byMyron Stolaroff in 1990.[ 5] It was developed byAlexander Shulgin and colleagues and was described in greater detail by them in 1991, including in Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved ).[ 5] [ 6] [ 1]
In his bookPiHKAL (Phenethylamines I Have Known and Loved ),Alexander Shulgin lists 2C-T-7's dose range as 10 to 30 mgorally and itsduration as 8 to 15 hours.[ 1] It producespsychedelic effects.[ 1] [ 5] [ 7] [ 8] InPiHKAL , Shulgin records that thehallucinations it produces are unique, and that the chemical may cause muscle tension and an altered vocal quality.[ 9] Shulgin rated it as one of the "magical half-dozen " most important psychedelic phenethylamines, together withmescaline ,2C-B , and2C-T-2 .[ 1]
2C-T-7 ismetabolized by themonoamine oxidase (MAO)enzymes MAO-A andMAO-B .[ 10] [ 11] Monoamine oxidase inhibitors (MAOIs) such asphenelzine ,tranylcypromine ,moclobemide , andselegiline may potentiate the effects of 2C-T-7.[ 10] [ 11] [ 12] This may result inoverdose and serioustoxicity .[ 12] [ 10]
Toxicity and deaths [ edit ] There have been at least three reported deaths related to 2C-T-7 use as of August 2007, mainly atinsufflated (snorted) doses of 30 mg or more.[ 13] [ 14] In the fall of 2000, a young healthy male died following insufflation of an excessive amount of 2C-T-7. Two additional deaths reported in April 2001 have been linked to 2C-T-7. These two deaths were reported by the DEA as being the result of the co-abuse of 2C-T-7 with MDMA.[ 15]
In January 2002,Rolling Stone published an article about 2C-T-7 entitled "The New (legal) Killer Drug".[ 16] Although the article suggested that the drug was legal, the legal status of 2C-T-7 was ambiguous at the time due to the United States'Federal Analogue Act .[ 17] A detailed response on the websitedisinfo.com challenged the accuracy of much of the reporting in the aforementionedRolling Stone article.[ 18] 2C-T-7 has since been officially made illegal and declared a schedule 1 substance in the United States.[ 19]
ThePartnership for a Drug-Free America reported in 2006 that 2C-T-7 can be lethal even in small doses;[ 20] however, they provide no source for their claim and of the three known deaths (as of August 2007) of 2C-T-7 intoxicated individuals, all involved either uncommonly large insufflated doses or the concomitant ingestion of other stimulants such asephedrine and/orMDMA .
All of the three aforementioned known deaths of individuals under the influence of 2C-T-7 occurred in those known to be either intoxicated with other stimulants such asephedrine orMDMA (which are known to be potentially lethal in certain situations or at excessive doses)[ 21] or after the individual insufflated an amount of 2C-T-7 much greater than necessary to induce the full range of effects typically sought after by users of the drug; for example, the reported 35 mg insufflated dose taken by the individual who died in the fall of 2000. This reported dose was characterized as "excessive" by the United States DEA.
2C-T-7 activities Target Affinity (Ki , nM)5-HT1A 520–878 5-HT1B ND 5-HT1D ND 5-HT1E ND 5-HT1F ND 5-HT2A 5.3–6.5 (Ki ) 1.2–130 (EC50 Tooltip half-maximal effective concentration ) 49–101% (Emax Tooltip maximal efficacy ) 5-HT2B ND (Ki ) 52–350 ( EC50 ) 45–46% ( Emax ) 5-HT2C 39–54 (Ki )ND ( EC50 ) ND ( Emax ) 5-HT3 ND 5-HT4 ND 5-HT5A ND 5-HT6 ND 5-HT7 ND α1A 13,000 α1B ,α1D ND α2A 180–335 α2B ,α2C ND β1 –β3 ND D1 15,000 D2 5,000 D3 7,500 D4 ,D5 ND H1 >25,000 H2 –H4 ND M1 –M5 ND I1 ND σ1 ,σ2 ND TAAR1 Tooltip Trace amine-associated receptor 1 311–560 (Ki ) (mouse) 10–33 (Ki ) (rat) 910 (EC50 ) (mouse) 79 ( EC50 ) (rat) >30,000 ( EC50 ) (human) 67% ( Emax ) (mouse) 83% ( Emax ) (rat) SERT Tooltip Serotonin transporter 12,000 (Ki ) 44,000 (IC50 Tooltip half-maximal inhibitory concentration )ND ( EC50 ) NET Tooltip Norepinephrine transporter 27,000 (Ki ) 135,000 (IC50 ) ND ( EC50 ) DAT Tooltip Dopamine transporter 34,000 (Ki ) 261,000 (IC50 ) ND ( EC50 ) MAO-A Tooltip Monoamine oxidase A 46,000 (IC50 ) MAO-B Tooltip Monoamine oxidase B 180,000 (IC50 ) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs: [ 22] [ 23] [ 24] [ 25] [ 26] [ 27] [ 28] [ 29]
The mechanism that produces the psychedelic effects of 2C-T-7 is most likely to result from action as a5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by most currently-known hallucinogenictryptamines andphenethylamines .[ 29] 2C-T-7 has structural and pharmacodynamic properties similar to those of2C-T-2 .[ 1]
Thechemical synthesis of 2C-T-7 has been described.[ 1] [ 2]
2C-T-7 was first described in thescientific literature byMyron Stolaroff by 1990.[ 5] It was developed byAlexander Shulgin andPeyton Jacob III .[ 5] [ 6] [ 1] Subsequently, 2C-T-7 was described in greater detail by Shulgin and colleagues in 1991.[ 6] [ 1]
Up untilOperation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanesesmartshops and online.[ 3] [ 4]
Society and culture [ edit ] Around the year 2000, 2C-T-7 began to change from an obscure chemical to a drug used at parties and clubs in North America and Europe as it became available through a number of grey-market commercial vendors. This aroused the attention of the authorities, and many countries have since scheduled the chemical.
In Australia,2C-T-2 and 2C-T-7 are covered by the country'sanalogue drug laws.
As of October 31, 2016, 2C-T-7 is a controlled substance (Schedule III) in Canada.[ 30]
As of October 2015 2C-T-7 is a controlled substance in China.[ 31]
2C-T-7 is scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".[ 32]
2C-T-7 is scheduled in Germany. (BTMG)
The Netherlands was the first country in the world to ban 2C-T-7, after being sold in smartshops for a short period. After 2C-T-2 was first banned, 2C-T-7 quickly appeared on the market, but was soon banned as well. 2C-T-7 is a list I drug of theOpium Law .
Schedule I in Sweden.[ 33] 2C-T-7 was first classified as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct on the Prohibition of Certain Goods Dangerous to Health ) as of April 1, 1999, under SFS 1999:58[ 34] that made it illegal to sell or possess.
In 1999,Alexander Shulgin was sent a copy of a letter from theBritish Home Office to several of its administrative associates that in effect placed all compounds listed inPiHKAL into Class A.[citation needed ]
On September 20, 2002, 2C-T-7 was classified as aSchedule I substance in the United States by an emergency ruling by theDEA . On March 18, 2004, the DEA published a Final Rule in the Federal Register permanently placing 2C-T-7 in Schedule I. (69 FR 12794)[ 19] [ 35] [ 36]
As of April 2024, law enforcement have encountered 2C-T-7 in 16 states, with the highest number of encounters being in Florida. Purchases made over the internet are believed by the DEA to be the most common source by which users of the drug acquire it in the United States, and one laboratory manufacturing the drug was discovered by police inLas Vegas, Nevada .[ 19]
^a b c d e f g h i j k l Shulgin A."PIHKAL #43" . ^a b Shulgin A, Manning T, Daley P (2011).The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley:Transform Press .ISBN 978-0-9630096-3-0 . ^a b Platoni K (May 1, 2002). "2C-T-7's Bad Trip". East Bay Express.In 1999 it made its first commercial appearance in the Netherlands' drug-dealing smart shops in both tablet and powder form. It was given the street name "Blue Mystic," perhaps in order to differentiate it from its chemical cousin, another Shulgin creation named 2C-T-2 ^a b O'Connell C (August 19, 2002)."A psychedelic summer" . Newsweek. ^a b c d e Clifford JS, Baldwin N, Brett J, Cerbo L, Demers-Gendreau C (July 1, 1990). "Treatment of alcoholism".Journal of Psychoactive Drugs .22 (3): 377.doi :10.1080/02791072.1990.10472568 .PMID 2286872 . ^a b c Shulgin AT, Shulgin A, Jacob P (January 1991)."Central nervous system (CNS) activity of two new psychoactive compounds" .Journal of Psychoactive Drugs .23 (1):95– 96.doi :10.1080/02791072.1991.10472583 .eISSN 2159-9777 .PMID 1941371 . Archived fromthe original on July 13, 2025. ^ Hardison C (2000)."An Amateur Qualitative Study of 48 2C-T-7 Subjective Bioassays" .maps.org . Bulletin of the Multidisciplinary Association for Psychedelic Studies MAPS. RetrievedOctober 30, 2023 . ^ "Erowid 2C-T-7 Vault: Sulfurous Samadhi: Stolaroff's & Well's Study" .erowid.org . February 6, 2001. RetrievedOctober 30, 2023 .^ Shulgin A (June 28, 2001)."2C-T-7" .Ask Dr Shulgin . Centre for Cognitive Liberty and Ethics (COLE). RetrievedAugust 28, 2009 .^a b c Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013)."2C or not 2C: phenethylamine designer drug review" .Journal of Medical Toxicology .9 (2):172– 178.doi :10.1007/s13181-013-0295-x .PMC 3657019 .PMID 23494844 . ^a b Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)".Biochemical Pharmacology .73 (2):287– 297.doi :10.1016/j.bcp.2006.09.022 .PMID 17067556 . ^a b Halman A, Kong G, Sarris J, Perkins D (January 2024)."Drug-drug interactions involving classic psychedelics: A systematic review" .Journal of Psychopharmacology .38 (1):3– 18.doi :10.1177/02698811231211219 .PMC 10851641 .PMID 37982394 . ^ Curtis B, Kemp P, Harty L, Choi C, Christensen D (October 2003). "Postmortem identification and quantitation of 2,5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD".Journal of Analytical Toxicology .27 (7):493– 498.doi :10.1093/jat/27.7.493 .PMID 14607005 .This compound was initially identified from a routine screening procedure in postmortem urine from a 20-year-old male that died in a local emergency room after reportedly insufflating 35 mg. ^ Platoni C (May 1, 2002). A psychedelic summer.East Bay Express (Report).In the same month, Joshua Robbins, a seventeen-year-old from Cordova, Tennessee, died after snorting between thirty and thirty-five milligrams of 2C-T-7, not long after taking several other stimulant drugs. According toRolling Stone , which ran an article on Robbins' death, in the twelve hours before he died Robbins also had consumed Ecstasy, nitrous oxide, and a 'mini-thin' containing ephedrine and guaifenisen or combined with stimulants such as MDMA ^ "2,5-dimethoxy-4-(n)-propylthiophenethylamine" .Drugs and Chemicals of Concern . Office of Diversion Control, Drug Enforcement Administration, U.S. Department of Justice. Archived fromthe original on October 20, 2008.^ "The New (Legal) Killer Drug".Rolling Stone , January 10, 2002, issue 888: 44–49. ^ 21 USC §813 ^ Lilly K (2002)."The new (hip) drug hysteria: a journey into rolling stone's abandonment of journalistic ethics" . Disinformation. Archived fromthe original on September 8, 2008. RetrievedNovember 10, 2008 . ^a b c "2,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE (Street Names: 2C-T-7, Blue Mystic, T7, Beautiful, Tripstay, Tweety-Bird Mescaline)" (PDF) . RetrievedSeptember 3, 2024 .^ America PF."2C-B, 2C-T-7" . Archived fromthe original on October 19, 2006. RetrievedOctober 4, 2006 . ^ Baldessarini RJ (May 1972). "Symposium: behavior modification by drugs. I. Pharmacology of the amphetamines".Pediatrics .49 (5):694– 701.doi :10.1542/peds.49.5.694 .PMID 4338459 .S2CID 245067669 . ^ "Kᵢ Database" .PDSP . May 10, 2025. RetrievedMay 10, 2025 .^ Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)".Neuropharmacology .99 :546– 553.doi :10.1016/j.neuropharm.2015.08.034 .PMID 26318099 . ^ Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)".Neuropharmacology .134 (Pt A):141– 148.doi :10.1016/j.neuropharm.2017.07.012 .PMID 28720478 . ^ Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor".Archives of Toxicology .94 (10):3449– 3460.Bibcode :2020ArTox..94.3449P .doi :10.1007/s00204-020-02836-w .hdl :1854/LU-8687071 .PMID 32627074 . ^ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases".Drug Testing and Analysis .11 (2):318– 324.doi :10.1002/dta.2494 .PMID 30188017 . ^ 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) .The Journal of Pharmacology and Experimental Therapeutics .357 (1):134– 144.doi :10.1124/jpet.115.229765 .PMID 26791601 . Archived fromthe original (PDF) on May 9, 2025. ^ Fantegrossi WE, Murnane KS, Reissig CJ (January 2008)."The behavioral pharmacology of hallucinogens" .Biochemical Pharmacology .75 (1):17– 33.doi :10.1016/j.bcp.2007.07.018 .PMC 2247373 .PMID 17977517 . ^a b Fantegrossi WE, Harrington AW, Eckler JR, Arshad S, Rabin RA, Winter JC, et al. (September 2005). "Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats".Psychopharmacology .181 (3):496– 503.doi :10.1007/s00213-005-0009-4 .hdl :2027.42/46369 .PMID 15983786 .S2CID 8108926 . ^ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)" .Gazette . Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada. May 4, 2016.^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. September 27, 2015. Archived fromthe original on October 1, 2015. RetrievedOctober 1, 2015 .^ "Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex" .^ "Läkemedelsverkets författningssamling" (PDF) .^ "Förordning (1999:58) om förbud mot vissa hälsofarliga varor - Karnov Open" .notisum.se . Archived fromthe original on October 4, 2013. RetrievedSeptember 15, 2013 .^ "2C-T-7 Fast Facts" (PDF) . U.S.Department of Justice .^ "List of Schedule 1 drugs on the DEA Office of Diversion Control website" . Archived fromthe original on August 27, 2009. RetrievedJuly 7, 2008 .
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
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 phenethylamines
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 ,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 DMBMPP 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 )