Psychedelic drug
Pharmaceutical compound
4-Acetoxy-N ,N -dimethyltryptamine (4-AcO-DMT or4-acetoxy-DMT ), also known asO -acetylpsilocinpsilacetin , is apsychedelic drug of thetryptamine family related topsilocybin andpsilocin .[ 1] [ 2] [ 3] [ 4] synthetic derivative of psilocin (4-HO-DMT) in which thehydroxyl group has beenacetylated , and is theanalogue of psilocybin (4-PO-DMT) in which thephosphate ester has been replaced with an acetateester .[ 1] [ 2] [ 3] prodrug of psilocin and isorally active similarly to psilocybin.[ 1] [ 2] [ 5]
As a prodrug of psilocin, 4-AcO-DMT acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A receptor .[ 1] [ 6] hallucinogenic effects of psilocin are thought to be mediated by activation of this receptor, although otherreceptors also contribute to its effects.[ 7] [ 8] [ 1] psilocybin mushrooms .[ 2] [ 5] [ 1] side effects such asnausea andbody load that can be caused by ingestion of whole psilocybin mushrooms.[ 2] [ 5] [ 1] onset and shorterduration than psilocybin.[ 5] safety .[ 1] potent by weight than psilocybin in animals when they are given atequimolar doses.[ 2]
4-AcO-DMT was first described in apatent byAlbert Hofmann in 1963 and itschemical synthesis was improved byDavid E. Nichols and colleagues in 1999.[ 2] [ 6] [ 3] scientific research , as the synthesis of psilocybin is more challenging and as psilocybin is acontrolled substance .[ 2] [ 6] [ 3] designer drug inEurope in 2009.[ 6] recreational drug in the 2010s and has been the most commonly used novel tryptamine.[ 2] [ 5] mushroom edibles in theUnited States as an alternative to psilocybin.[ 9] [ 10] [ 11] [ 12] synthetic shrooms ".[ 4] Amanita muscaria bath salts , and have been linked topoisonings and deaths.[ 13] [ 4] [ 12] [ 9]
4-AcO-DMT is not scheduled under United States law or any international drug schedules, including theUnited Nations 1971Convention on Psychotropic Substances , making it a potentially more accessible alternative to psilocybin for research.[ 2] in vivo is illegal and violates theFederal Analogue Act .[ 1]
Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary: some users report that 4-AcO-DMT lasts slightly longer, whilst others report that it lasts for a considerably shorter time.[ 14] [better source needed Many users report lessbody load and nausea compared with psilocin.[ 5] DMT than those produced by psilocin or psilocybin. Despite the preceding reports however, there have been no controlled clinical studies to distinguish the subjective effects of psilacetin, psilocin, and psilocybin.
Psilocin at molecular targetsTarget Affinity (Ki , nM) 5-HT1A 49–567 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy ) 5-HT1B 31–305 5-HT1D 19–36 5-HT1E 44–52 5-HT1F ND 5-HT2A 6.0–340 (Ki )EC50 ) Emax ) 5-HT2B 4.6–410 (Ki )EC50 ) Emax ) 5-HT2C 10–141 (Ki )EC50 ) Emax ) 5-HT3 >10,000 5-HT4 ND 5-HT5A 70–84 5-HT6 57–72 5-HT7 3.5–72 α1A –α1B >10,000 α2A 1,379–2,044 α2B 1,271–1,894 α2C 4,404 β1 –β2 >10,000 D1 20–>14,000 D2 3,700–>10,000 D3 101–8,900 D4 >10,000 D5 >10,000 H1 1,600–>10,000 H2 –H4 >10,000 M1 –M5 >10,000 σ1 >10,000 σ2 >10,000 I2 792 TAAR1 1,400 (Ki ) (rat)i ) (mouse)EC50 ) (rodent) EC50 ) (human) SERT Tooltip Serotonin transporter 3,650–>10,000 (Ki )IC50 Tooltip half-maximal inhibitory concentration )EC50 ) Emax ) NET Tooltip Norepinephrine transporter 13,000 (Ki )IC50 ) EC50 ) DAT Tooltip Dopamine transporter 6,000–>30,000 (Ki )IC50 ) EC50 ) Notes: The smaller the value, the more avidly psilocin interacts with the site.Sources: [ 15] [ 16] [ 17] [ 18] [ 19] [ 20] [ 21] [ 22] [ 23] [ 24] [ 25] [ 26] [ 27] [ 28] [ 29] [ 30] [ 31] [ 32] [ 33]
4-AcO-DMT is aprodrug ofpsilocin (4-HO-DMT).[ 2] non-selective agonist ofserotonin receptors , including of theserotonin 5-HT2A receptor .[ 1] psychedelic effects of 4-AcO-DMT are mediated specifically by activation of the serotonin 5-HT2A receptor.[ 1]
Similarly topsilocybin , psilocin, and otherserotonergic psychedelics , 4-AcO-DMT produces thehead-twitch response , a behavioral proxy of psychedelic effects, in rodents.[ 2] [ 6] [ 4] [ 34] DOM in rodentdrug discrimination tests.[ 35] hypolocomotion andhypothermia in rodents as with psilocin as well.[ 2]
There are noclinical studies of thepharmacokinetics of 4-AcO-DMT as of 2024.[ 2] pharmacokinetics of 4-AcO-DMT have been studied in rodents.[ 2] prodrug ofpsilocin similarly topsilocybin (4-PO-DMT).[ 2] intraperitoneal injection atequimolar doses, 4-AcO-DMT showed only 70% of therelative bioavailability ortotal exposure of psilocybin.[ 2] molecular weight .[ 2] minutes after administration were 75 to 90% of those of an equimolar dose of psilocybin.[ 2] elimination half-life of psilocin was approximately 30 minutes and did not differ between 4-AcO-DMT and psilocybin.[ 2] ester prodrugs like 4-AcO-DMT arecleaved into psilocin byesterase enzymes .[ 36]
A 2025in-vitro [ 37] minutes under conditions mimicking the human body (i.e., in human plasma).[ 37] [ 37]
4-AcO-DMT shown in powder form. 4-AcO-DMT can be obtained byacetylation of psilocin underalkaline or stronglyacidic conditions. It is, therefore, asynthetic compound. 4-AcO-DMT is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. It is not as difficult as psilocybin to synthesize.
Given enough time in unfavorable conditions, 4-AcO-DMT can sometimes turn into a degraded form which is brown in color and can even progress into a brown/black tar-like substance. Researchers hypothesize this is a polymerization reaction and is said to have no effect on thepotency of the substance. PreliminaryGCMS analysis of the closely relatedhomologue 4-AcO-DET suggests that this degraded form of 4-AcO-DMT consists mainly of the hydroxy form of the parent molecule.[ 38]
4-AcO-DMT is a lower homologue of4-AcO-MET , 4-AcO-DET,4-AcO-MiPT and4-AcO-DiPT . Otheranalogues of 4-AcO-DMT include4-AcO-DPT ,4-MeO-DMT , and4-PrO-DMT (O -propionylpsilocin).
4-AcO-DMT and several other esters of psilocin werepatented on January 16, 1963, bySandoz Ltd viaAlbert Hofmann and Franz Troxler.[ 39] [ 40] prodrug of psilocin, as is psilocybin, which occurs naturally in many species of psychedelic mushrooms. This is because the aromatic acetyl moiety on the 4th position of the indole ring system is subject to deacetylation in acidic conditions such as those found in the stomach.[ 41] O -acetylated psilocin, whereas psilocybin isO -phosphorylated.
Society and culture [ edit ] 4-AcO-DMT is not scheduled under any international drug schedules, including theUnited Nations 1971Convention on Psychotropic Substances , making it a potentially more accessible alternative to psilocybin for research.[ 42]
4-AcO-DMT can be considered an analog ofpsilocin making it a Schedule 9 prohibited substance in Australia under thePoisons Standard (October 2015).[ 43] [ 43]
4-AcO-DMT is prohibited in Czech republic except strictly limited research and therapeutical purposes.[ 44]
4-AcO-DMT is banned according to theBtMG since it's an ester of psilocin.[ 45]
4-AcO-DMT is technically illegal in Israel as of being a derivative of DMT.[citation needed
4-AcO-DMT is illegal in Italy as it is anester of a prohibited substance.[citation needed
The Riksdag added 4-AcO-DMT toNarcotic Drugs Punishments Act underswedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of January 25, 2017, published byMedical Products Agency (MPA) in regulationHSLF-FS 2017:1 listed as "4-acetoxi-N ,N -dimetyltryptamin".[ 46]
4-AcO-DMT, being an ester of psilocin, is aClass A drug in the UK under theMisuse of Drugs Act 1971 .[ 47]
In the United States, psilacetin can be legally sold and possessed when labeled as “not for human consumption” and intended solely for research purposes.[ 1] controlled substance analogue of psilocybin.[ 1] designer drugs .[ 48] [ 49]
4-AcO-DMT is listed (often under 4-Aco-DMT) as a controlled substance at the state level in multiple states in the USA, includingAlabama which has made it a schedule I at the state level on March 18, 2014, along with several other tryptamine analogs.[ 50]
^a b c d e f g h i j k l m Geiger HA, Wurst MG, Daniels RN (October 2018)."DARK Classics in Chemical Neuroscience: Psilocybin" (PDF) .ACS Chem Neurosci .9 (10):2438– 2447.doi :10.1021/acschemneuro.8b00186 .PMID 29956917 .A chemically modified psilocin precursor, known as psilacetin (20), O-acetylpsilocin, or 4-acetoxy-N,N-dimethyltryptamine, which replaces the phosphoryloxy group found on psilocybin with an acetoxy group, is also readily available. The substituted acetoxy group is believed to be metabolized in an equivalent manner to the phosphoryloxy group, both producing psilocin during first-pass metabolism.37 This simple modification skirts written laws in the United States when the product is clearly designated "not for human consumption," allowing pseudolegal import and possession for research purposes only; however, if it were to be used in vivo, the user would be in violation of the Federal Analogue Act.38 Although psilacetin has been hypothesized to act as an identical pharmacological substitute for psilocybin, many users report a small, yet significant, difference in the effects of each drug.39 Psilacetin is often described as having a faster onset of action without the anxiety and nausea associated with psilocybin-containing mushroom ingestion (which could be due to avoiding the ingestion of the significant amounts of chitin usually found in these mushrooms) and to have a shorter duration of action with a more peaceful experience throughout, leaving most users with a positive afterglow.37,39 ^a b c d e f g h i j k l m n o p q r s t Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ (2024)."In vivo validation of psilacetin as a prodrug yielding modestly lower peripheral psilocin exposure than psilocybin" .Front Psychiatry .14 1303365.doi :10.3389/fpsyt.2023.1303365 PMC 10804612 PMID 38264637 . ^a b c d Nichols D, Fescas S (1999)."Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" (PDF) .Synthesis .1999 (6):935– 938.CiteSeerX 10.1.1.690.8071 doi :10.1055/s-1999-3490 .S2CID 32044725 .Archived (PDF) from the original on 17 February 2012. Retrieved17 January 2012 . ^a b c d Wright W (24 June 2024)."4-AcO-DMT Is the Most Accessible (and Mysterious) Drug on the Market Right Now" .DoubleBlind Mag . Retrieved2 February 2025 . ^a b c d e f Palamar JJ, Acosta P (January 2020)."A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines" .Human Psychopharmacology .35 (1) e2719.doi :10.1002/hup.2719 .PMC 6995261 PMID 31909513 .4-AcO-DMT (4-acetoxyN,N-dimethyltryptamine, O-acetylpsilocin, or psilacetin) was the most prevalent tryptamine reported with 30.8% of the sample reporting use and two thirds (66.7%) of tryptamine users reporting use. 4-AcO-DMT—often pronounced as "4-akko-DMT"—was reported by most users as producing similar effects as psilocybin mushrooms with less nausea. One participant referred to this compound as "silly pills," which is a play on the name psilocybin. This particular compound was often preferred over natural mushrooms due to the lack of adverse side effects such as nausea, which the natural mushroom tends to produce. Thus, participants often suggested that 4-AcODMT allows one to achieve the same high as psilocybin without adverse physical effects such as nausea and heavy body load. One participant did complain of dry mouth and mentioned that although 4-AcO-DMT feels similar to psilocybin, he said it lacks the "organic" feel produced by psilocybin. [...] Of the most common tryptamines used by this sample, the majority of these compounds were first discovered or first synthesized as early as the 1930s (e.g., 5-MeO-DMT), 1950s (e.g., 4-AcO-DMT), or in the 1970s (e.g., 4-HO-MET and 5-MeO-DIPT). [...] 4-AcO-DMT was the most commonly used tryptamine by participants, and this compound also appears to be among the most prevalent novel tryptamines in recent years (Palamar & Le, 2019; PalmaConesa et al., 2017). [...] 4-AcO-DMT is often described as having a faster onset of action than psilocybin with a high of shorter duration, and as many of our participants noted, use allows them to avoid the nausea commonly associated mushroom ingestion (Geiger et al., 2018). Despite 4-AcO-DMT being among the most prevalent tryptamines, and having been discovered in the 1950s, little academic research has focused on recreational use of this compound. ^a b c d e Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. 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Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others Cyclized Ergolines /lysergamides (e.g.,LSD )β-Carbolines andHarmala alkaloidsharmine ,harmaline ,6-methoxyharmalan )Iboga alkaloids18-MAC ,18-MC ,coronaridine ,ibogaine ,ibogamine ,ME-18-MC ,noribogaine ,tabernanthine ,voacangine )Ibogalogs (e.g.,ibogainalog )O -MethylnordehydrobufoteninePartial ergolines (e.g.,NDTDI ,RU-28306 ,CT-5252 )Piperidinylethylindoles (e.g.,pip-T )Pyrrolidinylethylindoles (e.g.,pyr-T ,5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g.,MPMI ,4-HO-MPMI (lucigenol) ,5-MeO-MPMI )Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI) ,NEtPhOH-THPI )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF ,dimemebfe (5-MeO-BFE) ,mebfap )Benzothiophenes (e.g.,3-APBT )Indazolethylamines (e.g.,AL-38022A ,O -methyl-AL-34662Indenylethylamines (e.g.,C-DMT )Isotryptamines (e.g.,6-MeO-isoDMT ,Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g.,mefloquine )
Phenethylamines
Scalines 2C-x Others: 2C-B-AN 2C-DB 2C-G-x (e.g.,2C-G-3 ,2C-G-5 )β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx BOB ,BOD ,BOH-2C-B )HOT-x HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs 2CD-2-ETO ,2CD-5-ETO ,2CE-5-ETO ,2CE-5iPrO ,2CT2-5-ETO ,ASR-2001 (2CB-5PrO) )3C-x DOx 4C-x Ψ-PEA MDxx FLY 25x-NB (NBOMes) Others 2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g.,5-APB ,5-APDB ,6-APB ,6-APDB ,F ,F-2 ,F-22 )Benzothiophenes (e.g.,5-APBT ,6-APBT )CT-5172 DMAs (e.g.,2,4-DMA ,3,4-DMA )Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs 25D-NM-NDEAOP ,DOB-NDEPA ,DOI-NDEPA ,DOM-NDEPA ,DOTFM-NDEPA ,M-NDEPA ,TMA-2-NDEPA )PMA (4-MA) TMAs TMA-3 ,TMA-4 ,TMA-5 )TOMSO ZDCM-04 Cyclized 1-Aminomethylindanes (e.g.,2CB-Ind ,jimscaline )2-Aminoindanes (e.g.,DOM-AI )3-Benzazepines (e.g.,lorcaserin )3-Phenylpiperidines (e.g.,LPH-5 ,LPH-48 )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )DMBMPP (juncosamine) Ergolines /lysergamides (e.g.,LSD )Glaucine Partial ergolines (e.g.,NDTDI ,DEIMDHPCA ,DEMPDHPCA ,DEMTMPDHPCA ,DEMNDHPCA )Phenylcyclopropylamines (e.g.,DMCPA ,TMT )Phenyloxazolamines (aminorexes ) (e.g.,2C-B-aminorex )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 )Z3517967757 ZC-B
Lysergamides Others Arylpiperazines (e.g.,2C-B-PP ,2-NP ,mCPP ,MK-212 ,ORG-12962 ,pCPP ,pFPP ,quipazine ,TFMPP )Dihydrobenzoxazines (e.g.,efavirenz )Phenoxyethylamines (e.g.,CT-4719 ,ORG-37684 )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 )Quinazolinylethylamines (e.g.,RH-34 )Natural sources Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca andvinho de Jurema (e.g.,Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum Brosimum acutifolium (takini)Hallucinogenic snuffs (e.g.,Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene)Anadenanthera colubrina (vilca, cebil)Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g.,Psilocybe cubensis Psilocybe mexicana (teonanacatl)Lysergamides: Achnatherum robustum (sleepy grass)Epichloë spp.Ergot (Claviceps ) (e.g.,Claviceps purpurea Claviceps paspali Morning glory (Convolvulaceae) seeds (e.g.,Ipomoea tricolor (tlitliltzin, badoh negro;Ipomoea violacea )Ipomoea corymbosa (coaxihuitl, ololiúqui;Rivea Corymbosa ,Turbina Corymbosa )Argyreia nervosa (Hawaiian baby woodrose; HBWR)Periglandula spp.Periglandula ipomoeae Periglandula clandestina
5-HT1
5-HT1A
Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g.,etoperidone ,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione ,vilazodone ,vortioxetine )Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,lurasidone ,quetiapine ,ziprasidone )Azapirones (e.g.,buspirone ,eptapirone ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,methylergometrine (methylergonovine) ,methysergide ,pergolide )F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT ,5-MeO-DMT ,5-MT ,bufotenin ,DMT ,indorenate ,N-Me-5-HT ,psilocin ,psilocybin )TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Atypical antipsychotics (e.g.,iloperidone ,risperidone ,sertindole )AV965 Beta blockers (e.g.,alprenolol ,carteolol ,cyanopindolol ,iodocyanopindolol ,isamoltane ,oxprenolol ,penbutolol ,pindobind ,pindolol ,propranolol ,tertatolol )BMY-7378 CSP-2503 Dotarizine Ergolines (e.g.,metergoline )FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
5-HT1B
Agonists: Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB ,6-MAPB ,BK-5-MAPB ,BK-6-MAPB )Benzothiophenes (e.g.,5-MAPBT ,6-MAPBT ,BK-5-MAPBT )CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )mCPP Methylenedioxyphenethylamines (e.g.,MDMA ,methylone )PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LSD ,methysergide )GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan ,avitriptan ,donitriptan ,eletriptan ,frovatriptan ,naratriptan ,rizatriptan ,sumatriptan ,zolmitriptan )Tryptamines (e.g.,5-BT ,5-CT ,5-Et-DMT ,5-MT ,5-(nonyloxy)tryptamine ,DMT )
5-HT1E
5-HT1F
5-HT2
5-HT2A
Agonists: 25H/NB series (e.g.,25I-NBF ,25I-NBMD ,25I-NBOH ,25I-NBOMe ,25B-NBOMe ,25C-NBOMe ,25TFM-NBOMe ,2CBCB-NBOMe ,25CN-NBOH ,2CBFly-NBOMe )2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g.,DOB ,DOC ,DOI ,DOM )Efavirenz Ergolines (e.g.,1P-LSD ,ALD-52 ,bromocriptine ,cabergoline ,ergine (LSA) ,ergometrine (ergonovine) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,methylergometrine (methylergonovine) ,pergolide )Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,BZP ,quipazine ,TFMPP )Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g.,cyproheptadine ,hydroxyzine ,ketotifen ,perlapine )AMDA Atypical antipsychotics (e.g.,amperozide ,aripiprazole ,asenapine ,blonanserin ,brexpiprazole ,carpipramine ,clocapramine ,clorotepine ,clozapine ,fluperlapine ,gevotroline ,iloperidone ,lurasidone ,melperone ,mosapramine ,ocaperidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,zicronapine ,ziprasidone ,zotepine )Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline )Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,haloperidol ,loxapine ,perphenazine ,pimozide ,pipamperone ,prochlorperazine ,setoperone ,spiperone ,spiramide ,thioridazine ,thiothixene ,trifluoperazine )Volinanserin Xylamidine Yohimbine
5-HT2B
Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g.,chlorphentermine ,cloforex ,dexfenfluramine ,fenfluramine ,levofenfluramine ,norfenfluramine )BW-723C86 DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,cabergoline ,dihydroergocryptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )Piperazines (e.g.,TFMPP )PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,α-Me-5-HT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: Agomelatine Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,N-desalkylquetiapine (norquetiapine) ,N-desmethylclozapine (norclozapine) ,olanzapine ,pipamperone ,quetiapine ,risperidone ,ziprasidone )Cyproheptadine EGIS-7625 Ergolines (e.g.,amesergide ,bromocriptine ,lisuride ,LY-53857 ,LY-272015 ,mesulergine )Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Trazodone Typical antipsychotics (e.g.,chlorpromazine )TIK-301 Yohimbine
5-HT2C
Agonists: 2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,ALD-52 ,cabergoline ,dihydroergotamine ,ergine (LSA) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,pergolide )Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,aripiprazole ,BZP ,mCPP ,quipazine ,TFMPP )PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin WAY-629 WAY-161503 YM-348 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,melperone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,ziprasidone ,zotepine )Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide ,bromocriptine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine ,pimozide ,pipamperone ,thioridazine )Xylamidine
5-HT3 –7
5-HT3
Agonists: Alcohols (e.g.,butanol ,ethanol (alcohol) ,trichloroethanol )m-CPBG Phenylbiguanide Piperazines (e.g.,BZP ,mCPP ,quipazine )RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g.,2-Me-5-HT ,5-CT ,bufotenidine (5-HTQ) )Volatiles/gases (e.g.,halothane ,isoflurane ,toluene ,trichloroethane )YM-31636 Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g.,clozapine ,olanzapine ,quetiapine )Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Thujone Tropanserin Tropisetron Typical antipsychotics (e.g.,loxapine )Volatiles/gases (e.g.,nitrous oxide ,sevoflurane ,xenon )Vortioxetine Zacopride Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g.,dihydroergocryptine ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,mesulergine ,metergoline ,methysergide )Hypidone Serotonin (5-HT) Tryptamines (e.g.,2-Me-5-HT ,5-BT ,5-CT ,5-MT ,Bufotenin ,E-6801 ,E-6837 ,EMD-386088 ,EMDT ,LY-586713 ,N-Me-5-HT ,ST-1936 ,tryptamine )WAY-181187 WAY-208466 Antagonists: ABT-354 Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,olanzapine ,tiospirone )AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,clorotepine ,clozapine ,fluperlapine ,olanzapine ,risperidone ,sertindole ,tiospirone ,ziprasidone ,zotepine )Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148) ,amesergide ,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,imipramine )Typical antipsychotics (e.g.,acetophenazine ,chlorpromazine ,chlorprothixene ,fluphenazine ,loxapine ,pimozide )Vortioxetine
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
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
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 esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-NiPT 5-HO-DPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS;O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O -methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ;N ,N ,N -TMS) Bufotenin (5-HO-DMT;N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 Cyclized tryptamines 5-MeO-IsoqT Barettin Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD )Harmala alkaloidsβ-carbolines (e.g.,5-methoxyharmalan ,6-MeO-THH ,6-methoxyharmalan ,9-Me-BC ,β-carboline (norharman) ,fenharmane ,harmaline ,harmalol ,harmane ,harmine ,LY-266,097 ,pinoline ,tetrahydroharmine ,tryptoline )Iboga alkaloidsibogaine ,ibogamine ,noribogaine ,tabernanthine )Ibogalogs (e.g.,catharanthalog ,fluorogainalog ,ibogainalog ,ibogaminalog (DM-506) ,LS-22925 ,noribogainalog ,noribogaminalog ,PHA-57378 ,PNU-22394 ,tabernanthalog )Imidazolylindoles (e.g.,AGH-107 ,AGH-192 ,AH-494 )Metralindole Morpholinylethylindoles (e.g.,mor-T ,5-MeO-mor-T )Partial ergolines and lysergamides (e.g.,NDTDI ,RU-27849 ,RU-28251 ,RU-28306 ,FHATHBIN ,LY-178210 ,Bay R 1531 (LY-197206) ,LY-293284 ,10,11-seco-LSD ,10,11-secoergoline (α,N -Pip-T) ,CT-5252 )Pertines (e.g.,alpertine ,milipertine ,oxypertine ,solypertine )Piperidinylethylindoles (e.g.,pip-T ,5-MeO-pip-T ,indolylethylfentanyl )Pyrrolidinylethylindoles (e.g.,pyr-T ,4-HO-pyr-T ,5-MeO-pyr-T ,4-F-5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g.,MPMI ,4-HO-MPMI (lucigenol) ,5F-MPMI ,5-MeO-MPMI ,CP-122288 ,CP-135807 ,eletriptan )Tetrahydrocarbazolamines (e.g.,ciclindole ,flucindole ,frovatriptan ,LY-344864 ,ramatroban )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 ,NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g.,bufothionine ,O -methylnordehydrobufotenineYohimbans (e.g.,yohimbine ,rauwolscine ,spegatrine ,corynanthine ,ajmalicine ,reserpine ,deserpidine ,rescinnamine )Isotryptamines Related compounds 2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline ,alosetron ,gevotroline ,latrepirdine ,lurosetron ,mebhydrolin ,tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,5-MeO-DiBF ,BPAP ,3-F-BPAP ,dimemebfe ,mebfap ,oxa-noribogaine )Benzothiophenes (e.g.,3-APBT )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g.,HT ,DMHT )I-32 IAL IN-399 Indazolethylamines (e.g.,AL-34662 ,AL-38022A ,O -methyl-AL-34662VU6067416 ,YM-348 )Indenylethylamines (e.g.,C-DMT )Indolizinylethylamines (e.g.,TACT908 (2ZEDMA) ,1ZP2MA ,1Z2MAP1O )Indolylaminopropanes (e.g.,1-API ,2-API ,4-API ,5-API (5-IT; PAL-571) ,6-API (6-IT) ,7-API )Iprindole Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan ,LY-334370 ,naratriptan ) Ondansetron Oxazinopyridoindoles (e.g.,IHCH-8134 )Phenethylamines (e.g.,phenethylamine ,amphetamine )Piperidinylbenzimidazolines (e.g.,benperidol ,timiperone )Piperazinylbenzisothiazoles (e.g.,lurasidone ,perospirone ,tiospirone ,ziprasidone )Piperidinylbenzisoxazoles (e.g.,iloperidone ,milsaperidone ,ocaperidone ,paliperidone ,risperidone )Piperidinylindoles (e.g.,BRL-54443 ,LY-334370 ,naratriptan ,sertindole ,SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g.,droperidol )Pyridinylindoles (e.g.,tepirindole )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 ,IHCH-7079 ,IHCH-7086 ,lumateperone ,deulumateperone ,ITI-1549 )Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA) ,3-pyrrolylethylamine (3-NEA) ,3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g.,WAY-208466 )Quinolinylethylamines (e.g.,mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088 ,LY-367265 ,RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g.,(R )-69 (3IQ) ,(R )-70 ,CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
