Metabolite of the amino acid tryptophan
Pharmaceutical compound
Tryptamine , also known as2-(3-indolyl)ethylamine , is anindolamine metabolite of theessential amino acid tryptophan .[ 9] [ 10] indole —a fusedbenzene andpyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being theheterocyclic nitrogen).[ 9] neuromodulators includingmelatonin ,serotonin ,bufotenin and psychedelic derivatives such asdimethyltryptamine (DMT),psilocybin ,psilocin andothers .[ 11] [ 12] [ 13]
Tryptamine has been shown to activateserotonin receptors [ 5] [ 14] trace amine-associated receptors expressed in the mammalian brain, and regulates the activity ofdopaminergic ,serotonergic andglutamatergic systems.[ 15] [ 16] 5-HT4 receptors and regulates gastrointestinal motility.[ 10] [ 17] [ 18]
Multiple tryptamine-derived drugs have been developed to treatmigraines , while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.[ 19] [ 20] [ 21]
Natural occurrences [ edit ] For a list of plants, fungi and animals containing tryptamines, seeList of psychoactive plants andList of naturally occurring tryptamines .
Endogenous levels of tryptamine in the mammalian brain are less than 100 ng per gram of tissue.[ 12] [ 16] bipolar depression andschizophrenia .[ 22]
Mammalian gut microbiome [ edit ] Tryptamine is relatively abundant in thegut and feces of humans and rodents.[ 10] [ 17] Commensal bacteria, includingRuminococcus gnavus andClostridium sporogenes gastrointestinal tract , possess theenzyme tryptophandecarboxylase , which aids in the conversion of dietary tryptophan to tryptamine.[ 10] ligand for gut epithelial serotonin type 4 (5-HT4 ) receptors and regulates gastrointestinalelectrolyte balance through colonic secretions.[ 17]
To yield tryptaminein vivo , tryptophan decarboxylase removes the carboxylic acid group on the α-carbon oftryptophan .[ 12] serotonin andmelatonin ; however, these pathways do not occur naturally as the main pathway for endogenous neurotransmitter synthesis.[ 23]
Monoamine oxidases A and B are the primary enzymes involved in tryptamine metabolism to produceindole-3-acetaldehyde , however it is unclear which isoform is specific to tryptamine degradation.[ 24]
Conversion of tryptophan to tryptamine, followed by its degradation to indole-3-acetaldehyde. Biological activity [ edit ] Tryptamine target activities Target Affinity (Ki , nM)Species 5-HT1A 32–105 (Ki )EC50 Tooltip half-maximal effective concentration )ND ( Emax Tooltip maximal efficacy ) Human 5-HT1B 36–525 Human 5-HT1D 23–521 Human 5-HT1E 2,559 Human 5-HT1F 2,409 Human 5-HT2A 37–4,070 (Ki )EC50 ) Emax ) Human 5-HT2B 25–113 (Ki )EC50 ) Emax ) Human 5-HT2C 17–3,000 (Ki )EC50 ) Emax ) Human 5-HT3 ND ND 5-HT4 >10,000EC50 ) Emax ) Mouse 5-HT5A ND ND 5-HT6 70–438 Human 5-HT7 148–158 Human α2A 19,000 Rat TAAR1 Tooltip Human trace amine-associated receptor 1 1,400 (Ki )EC50 ) Emax )i ) EC50 ) Emax )i ) EC50 ) Emax ) Mouse SERT Tooltip Serotonin transporter 32.6 (EC50 )a Rat NET Tooltip Norepinephrine transporter 716 (EC50 )a Rat DAT Tooltip Dopamine transporter 164 (EC50 )a Rat Note: The smaller the value, the more avidly the compound binds to or activates the site.Footnotes: a =Neurotransmitter release .Refs: Main: [ 25] [ 26] Additional: [ 27] [ 28] [ 29] [ 5] [ 30] [ 31] [ 32] [ 33] [ 34] [ 35] [ 36]
Serotonin receptor agonist [ edit ] Tryptamine is known to act as aserotonin receptor agonist , although itspotency is limited by rapidinactivation bymonoamine oxidases .[ 4] [ 5] [ 14] [ 37] [ 38] [ 39] full agonist of theserotonin 5-HT2A receptor (EC50 Tooltip half-maximal effective concentration = 7.36 ± 0.56 nM;Emax = 104 ± 4%).[ 5] 2A receptorβ-arrestin pathway (EC50 = 3,485 ± 234 nM; Emax = 108 ± 16%).[ 5] 2A receptor, tryptamine was found to be inactive at the serotonin 5-HT1A receptor .[ 5]
Gastrointestinal motility [ edit ] Tryptamine produced by mutualistic bacteria in the human gut activates serotonin GPCRs ubiquitously expressed along the colonic epithelium.[ 17] 4 receptor undergoes a conformational change which allows itsGs alpha subunit to exchangeGDP forGTP , and its liberation from the 5-HT4 receptor and βγ subunit.[ 17] s activatesadenylyl cyclase , which catalyzes the conversion ofATP intocyclic adenosine monophosphate (cAMP).[ 17] [ 18] [ 40]
Tryptamine promotes intestinal motility by activating serotonin receptors in the gut to increase colonic secretions. Monoamine releasing agent [ edit ] Tryptamine has been found to act as amonoamine releasing agent (MRA).[ 4] [ 5] [ 30] serotonin ,dopamine , andnorepinephrine , in that order of potency (EC50 = 32.6 nM, 164 nM, and 716 nM, respectively).[ 4] [ 5] [ 30] serotonin–norepinephrine–dopamine releasing agent (SNDRA).[ 5] [ 30]
Monoamine release of tryptamine and related agents (EC50 Tooltip Half maximal effective concentration , nM) Compound 5-HT Tooltip Serotonin NE Tooltip Norepinephrine DA Tooltip Dopamine Ref Tryptamine 32.6 716 164 [ 5] [ 30] Serotonin 44.4 >10,000 ≥1,960 [ 41] [ 42] Phenethylamine >10,000 10.9 39.5 [ 43] [ 44] [ 42] Tyramine 2,775 40.6 119 [ 41] [ 42] 5-Methoxytryptamine 2,169 >10,000 >10,000 [ 30] N -Methyltryptamine22.4 733 321 [ 5] Dimethyltryptamine 114 4,166 >10,000 [ 5] Psilocin 561 >10,000 >10,000 [ 45] [ 5] Bufotenin 30.5 >10,000 >10,000 [ 5] 5-MeO-DMT >10,000 >10,000 >10,000 [ 46] α-Methyltryptamine 21.7–68 79–112 78.6–180 [ 46] α-Ethyltryptamine 23.2 640 232 [ 30] D -Amphetamine698–1,765 6.6–7.2 5.8–24.8 [ 41] [ 47] Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Refs: [ 48] [ 49]
Monoaminergic activity enhancer [ edit ] Tryptamine is amonoaminergic activity enhancer (MAE) ofserotonin ,norepinephrine , anddopamine in addition to itsserotonin receptor agonism .[ 50] [ 51] action potential -mediated release of thesemonoamine neurotransmitters .[ 50] [ 51] [ 52] [ 53] Synthetic and morepotent MAEs likebenzofuranylpropylaminopentane (BPAP) andindolylpropylaminopentane (IPAP) have beenderived from tryptamine.[ 50] [ 51] [ 54] [ 55] [ 56]
Tryptamine is an agonist of thetrace amine-associated receptor 1 (TAAR1).[ 28] potent TAAR1full agonist in rats, a weak TAAR1 full agonist in mice, and a very weak TAAR1partial agonist in humans.[ 28] neuromodulator in some species via activation of TAAR1 signaling.[ 28] [ 57]
The TAAR1 is a stimulatoryG protein-coupled receptor (GPCR) that is weaklyexpressed in theintracellular compartment of bothpre- andpostsynaptic neurons.[ 16] monoaminergic neurotransmission , for instance by activatingG protein-coupled inwardly-rectifying potassium channels (GIRKs) and reducingneuronal firing via facilitation ofmembrane hyperpolarization through theefflux ofpotassium ions .[ 28] [ 58]
TAAR1 agonists are under investigation as a novel treatment forneuropsychiatric conditions likeschizophrenia ,drug addiction , anddepression .[ 16] ventral tegmental area (VTA) and serotonin systems in thedorsal raphe nuclei (DRN).[ 16] locus formood disorders and schizophrenia.[ 28] neuropsychiatric disorders , as TAAR1 agonists produceantipsychotic -like,anti-addictive , andantidepressant -like effects in animals.[ 58] [ 28]
TAAR1 affinities and activational potencies of tryptamines[ 28] [ 29] Compound Human TAAR1 Mouse TAAR1 Rat TAAR1 EC50 (nM) Ki (nM) EC50 (nM) Ki (nM) EC50 (nM) Ki (nM) Tryptamine 21,000 N/A 2,700 1,400 410 130 Serotonin >50,000 N/A >50,000 N/A 5,200 N/A Psilocin >30,000 N/A 2,700 17,000 920 1,400 Dimethyltryptamine >10,000 N/A 1,200 3,300 1,500 22,000 Notes: (1)EC50 and Ki values are in nanomolar (nM). (2)EC50 reflects the concentration required to elicit 50% of the maximum TAAR1 response. (3) The smaller the Ki value, the stronger the compound binds to the receptor.
Effects in animals and humans [ edit ] In a published clinical study, tryptamine, at a total dose of 23 to 277 mg byintravenous infusion , producedhallucinogenic effects or perceptual disturbances similar to those of small doses oflysergic acid diethylamide (LSD).[ 1] [ 2] [ 5] [ 3] pupil dilation , increasedblood pressure , and increased force of thepatellar reflex .[ 1] [ 5] [ 2] [ 3] side effects includingnausea ,vomiting ,dizziness ,tingling sensations,sweating , and bodily heaviness among others as well.[ 1] [ 3] heart rate orrespiratory rate .[ 3] onset of the effects was rapid and theduration was very short.[ 4] [ 5] [ 2] [ 3] metabolism of tryptamine bymonoamine oxidase (MAO) and its very shortelimination half-life .[ 4] [ 5] [ 2] [ 3]
In animals, tryptamine, alone and/or in combination with amonoamine oxidase inhibitor (MAOI), produces behavioral changes such ashyperlocomotion and reversal ofreserpine -inducedbehavioral depression .[ 1] [ 4] [ 59] [ 60] hyperthermia ,tachycardia ,myoclonus , andseizures orconvulsions , among others.[ 1] [ 4] [ 59] [ 60] head-twitch response in rodents have been mixed, with some studies reporting no effect,[ 61] [ 62] [ 63] [ 64] [ 65] 5-hydroxytryptophan (5-HTP)-induced head twitches.[ 59] [ 61] [ 66] [ 67] [ 68] serotonin receptor antagonists likemetergoline ,metitepine (methiothepin), andcyproheptadine .[ 4] [ 59] [ 60] [ 1] [ 4] [ 60] [ 1]
Tryptamine seems to also elevateprolactin andcortisol levels in animals and/or humans.[ 60]
TheLD50 Tooltip median lethal dose values of tryptamine in animals include 100 mg/kg i.p. in mice, 500 mg/kg s.c. in mice, and 223 mg/kg i.p. in rats.[ 69]
Tryptamine producedendogenously oradministered peripherally is readily able to cross theblood–brain barrier and enter thecentral nervous system .[ 60] [ 59] serotonin , which isperipherally selective .[ 60]
Tryptamine ismetabolized bymonoamine oxidase (MAO) to formindole-3-acetic acid (IAA).[ 60] [ 4] [ 59] elimination half-life andduration as very short.[ 4] [ 5] [ 2] [ 3] dimethyltryptamine (DMT).[ 1] [ 59] exogenous tryptamine are strongly augmented bymonoamine oxidase inhibitors (MAOIs).[ 4] [ 59]
Tryptamine isexcreted inurine and its rate of urinary excretion has been reported to bepH -dependent.[ 3] [ 6] [ 7]
Tryptamine is asubstituted tryptamine derivative andtrace amine and isstructurally related to theamino acid tryptophan .[ 2]
The experimentallog P of tryptamine is 1.55.[ 69]
Thechemical synthesis of tryptamine has been described.[ 2]
Theendogenous monoamine neurotransmitters serotonin (5-hydroxytryptamine or 5-HT) andmelatonin (5-methoxy-N -acetyltryptamine), as well as trace amines likeN -methyltryptamineN ,N -dimethyltryptaminebufotenin (N ,N -dimethylserotonin), arederivatives of tryptamine.[ 2]
All tryptamine derivatives possess a modified 2-aminoethyl group and/or the addition of a substituent on the indole. A variety of drugs, including bothnaturally occurring andpharmaceutical substances, are derivatives of tryptamine.[ 2] psilocybin ,psilocin , DMT, and5-MeO-DMT ; tryptaminestimulants ,entactogens , psychedelics, and/orantidepressants likeα-methyltryptamine (αMT) andα-ethyltryptamine (αET);triptan antimigraine agents likesumatriptan ; certainantipsychotics likeoxypertine ; and thesleep aid melatonin .[ 2]
Various other drugs, includingergolines andlysergamides like the psychedeliclysergic acid diethylamide (LSD), the antimigraine agentsergotamine ,dihydroergotamine , andmethysergide , and theantiparkinsonian agents bromocriptine ,cabergoline ,lisuride , andpergolide ;β-carbolines likeharmine (some of which aremonoamine oxidase inhibitors (MAOIs));Iboga alkaloidshallucinogen ibogaine ;yohimbans like theα2 blocker yohimbine ; antipsychotics likeciclindole andflucindole ; and the MAOI antidepressantmetralindole , can all be thought of ascyclized tryptamine derivatives.[ 2]
Drugs very closely related to tryptamines, but technically not tryptamines themselves, include certain triptans likeavitriptan andnaratriptan ; the antipsychoticssertindole andtepirindole ; and the MAOI antidepressantspirlindole andtetrindole .
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"Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain".Bioorganic & Medicinal Chemistry .9 (5):1197– 1212.doi :10.1016/s0968-0896(01)00002-5 .PMID 11377178 . ^ Knoll J, Yoneda F, Knoll B, Ohde H, Miklya I (December 1999)."(-)1-(Benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain" .British Journal of Pharmacology .128 (8):1723– 1732.doi :10.1038/sj.bjp.0702995 .PMC 1571822 PMID 10588928 . ^ Zucchi R, Chiellini G, Scanlan TS, Grandy DK (December 2006)."Trace amine-associated receptors and their ligands" .British Journal of Pharmacology .149 (8):967– 978.doi :10.1038/sj.bjp.0706948 .PMC 2014643 PMID 17088868 . ^a b Grandy DK, Miller GM, Li JX (February 2016)." .Drug and Alcohol Dependence .159 :9– 16.doi :10.1016/j.drugalcdep.2015.11.014 .PMC 4724540 PMID 26644139 . ^a b c d e f g h Kellar KJ, Cascio CS (1986). "Tryptamine and Phenylethylamine Recognition Sites in Brain".Receptor Binding . Vol. 4. New Jersey: Humana Press. pp. 119– 138.doi :10.1385/0-89603-078-4:119 .ISBN 978-0-89603-078-7 ^a b c d e f g h Murphy DL, Tamarkin L, Garrick NA, Taylor PL, Markey SP (1985). "Trace Indoleamines in the Central Nervous System".Neuropsychopharmacology of the Trace Amines . Totowa, NJ: Humana Press. pp. 343– 360.doi :10.1007/978-1-4612-5010-4_36 .ISBN 978-1-4612-9397-2 ^a b Jones RS (June 1981)."In vivo pharmacological studies on the interactions between tryptamine and 5-hydroxytryptamine" .British Journal of Pharmacology .73 (2):485– 493.doi :10.1111/j.1476-5381.1981.tb10447.x .PMC 2071674 PMID 6972243 . ^ Yamada J, Sugimoto Y, Horisaka K (January 1987). "The behavioural effects of intravenously administered tryptamine in mice".Neuropharmacology .26 (1):49– 53.doi :10.1016/0028-3908(87)90043-8 .PMID 3561719 . ^ Haberzettl R, Bert B, Fink H, Fox MA (November 2013)."Animal models of the serotonin syndrome: a systematic review" .Behavioural Brain Research .256 :328– 345.doi :10.1016/j.bbr.2013.08.045 PMID 24004848 . ^ Sugimoto Y, Yamada J, Horisaka K (January 1986). "Effect of tryptamine on the behavior of mice".Journal of Pharmacobio-Dynamics .9 (1):68– 73.doi :10.1248/bpb1978.9.68 .PMID 2940357 . ^ Orikasa S, Sloley BD (1988). "Effects of 5,7-dihydroxytryptamine and 6-hydroxydopamine on head-twitch response induced by serotonin, p-chloroamphetamine, and tryptamine in mice".Psychopharmacology .95 (1):124– 131.doi :10.1007/BF00212780 .PMID 3133691 . ^ Irons J, Robinson CM, Marsden CA (1984). "5ht Involvement in Tryptamine Induced Behaviour in Mice".Neurobiology of the Trace Amines . Totowa, NJ: Humana Press. pp. 423– 427.doi :10.1007/978-1-4612-5312-9_35 .ISBN 978-1-4612-9781-9 ^ Canal CE, Morgan D (2012)."Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model" .Drug Testing and Analysis .4 (7– 8):556– 576.doi :10.1002/dta.1333 .PMC 3722587 PMID 22517680 . ^ Kozlenkov A, González-Maeso J (2013). "Animal Models and Hallucinogenic Drugs".The Neuroscience of Hallucinations . New York, NY: Springer New York. pp. 253– 277.doi :10.1007/978-1-4614-4121-2_14 .ISBN 978-1-4614-4120-5 ^a b "Tryptamine" .PubChem . Retrieved7 November 2024 .
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 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 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
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
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Tryptamines 1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan 4-Hydroxytryptamines 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 -methylnordehydrobufoteninedehydrobufotenine )Yohimbans (e.g.,yohimbine ,rauwolscine ,spegatrine ,corynanthine ,ajmalicine ,reserpine ,deserpidine ,rescinnamine )Isotryptamines Related compounds 2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline ,alosetron ,gevotroline ,latrepirdine ,lurosetron ,mebhydrolin ,tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,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)
