Chemical compound
Pharmaceutical compound
Dimethoxybromoamphetamine (DOB ), also known asbrolamfetamine (INN Tooltip International Nonproprietary Name ),[ 2] psychedelic drug of thephenethylamine ,amphetamine , andDOx families.[ 3] DOTFM ,FLY compounds likeBromo-DragonFLY , andNBOMe compounds like25I-NBOMe , DOB was the mostpotent known phenethylamine psychedelic.[ 3]
The drug acts as anagonist of theserotonin 5-HT2 receptors , including of the serotonin5-HT2A receptor .[ 4] [ 5]
DOB was firstsynthesized byAlexander Shulgin in 1967 and was described by him and his colleagues in thescientific literature in 1971.[ 6] [ 7] PiHKAL Phenethylamines I Have Known and Loved ).[ 6]
In his bookPiHKAL Alexander Shulgin gives the dose range of DOB as 1 to 3 mg and itsduration as 18 to 30 hours.[ 6] mg forracemic DOB and 1 to 2 mg for the preferentially active (R )-DOBenantiomer , while the duration is stated as being extremely long, a plateau occurring between 4 to 10 hours, and returning to baseline after 24 to 36 hours.[ 3] closed-eye andopen-eye psychedelic visuals andintrospection , among others.[ 6] [ 3]
At a low sub-hallucinogenic dose of 0.4 mg DOB, the drug was alsopsychoactive and produced effects including enhancedvisual perception , some strengthening of colors, enrichedemotional affect , a comfortable and good feeling, and colorful and importantdreams .[ 3]
Side effects of DOB includebody load ,muscle tremors ,muscle cramps ,attention lapses described as "littlefugue states ",sleeping difficulties , andbizarre dreams .[ 3]
Overdose of DOB has been reported to producecardiovascular symptoms andconvulsions .[ 3] arterial spasm .[ 8] vasodilators , such astolazoline .[ 8] mg overdose resulted in death, while a 75 mg overdose in a person withtolerance resulted inergotism -like complications that requiredamputation .[ 3]
DOB may interact synergistically withalcohol .[ 3]
DOB activities Target Affinity (Ki , nM)5-HT1A 2,550–7,904 5-HT1B 941 5-HT1D 636 5-HT1E 556–1,427 5-HT1F ND 5-HT2A 0.6–81 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy ) 5-HT2B 2.9–44 (Ki )EC50 ) Emax ) 5-HT2C 1.3–78 (Ki )EC50 ) Emax ) 5-HT3 >10,000 5-HT4 ND 5-HT5A 5,311 5-HT6 5,535 5-HT7 506 α1A ,α1B >10,000 α1D ND α2A 4,266 α2B 1,527 α2C 594 β1 2,425 β2 303 D1 ,D2 >10,000 D3 808 D4 ,D5 >10,000 H1 9,120 H2 –H4 >10,000 M1 ,M2 >10,000 M3 1,152 M4 ,M5 >10,000 TAAR1 >1,000 I1 1,596 σ1 2,193 σ2 >10,000 SERT Tooltip Serotonin transporter 8,538 (Ki ) NET Tooltip Norepinephrine transporter >10,000 (Ki ) DAT Tooltip Dopamine transporter >10,000 (Ki ) MAO-A Tooltip Monoamine oxidase A 100,000 (IC50 Tooltip half-maximal inhibitory concentration ) (rat) MAO-B Tooltip Monoamine oxidase B >100,000 (IC50 ) (rat) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs: [ 9] [ 10] [ 4] [ 11] [ 12] [ 13] [ 14] [ 15] [ 5] [ 16] [ 17]
DOB is aserotonin 5-HT2A ,5-HT2B , and5-HT2C receptor agonist .[ 4] [ 5] agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the5-HT2 receptor subfamily.
It is a very weakagonist of the humantrace amine-associated receptor 1 (TAAR1) and a weak agonist of therhesus monkey TAAR1.[ 17] [ 5] serotonin releasing agent MDMA , DOB does not produceprotein kinase C (PKC) activation in the brains of rodentsin vivo [ 18] [ 19] uptake by theserotonin transporter (SERT).[ 18] [ 19]
DOB has been found to reduceaggression in rats.[ 20] [ 21]
DOB is one of the most potent compounds inPiHKAL ; while the active dose is similar to that ofDOI , another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by serotonin 5-HT2 receptors.[ 22]
Tabs of DOB, confiscated by police inConcord, California in 2006. The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has astereocenter andR -(−)-DOB is theeutomer . This is an important finding as it is suggestive that it is targeting different receptors relative to most otherphenethylamines (e.g.MDMA ) where theR -isomer serves as thedistomer .
Omission of the amphetamine related α-methyl leads to2C-B , a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist.[citation needed Otheranalogues of DOB include4C-B ,Bromo-DragonFLY ,DOB-FLY , and25B-NBOMe , among others.
DOB was firstsynthesized byAlexander Shulgin in 1967.[ 6] scientific literature in a paper by Shulgin,Claudio Naranjo , and another colleague in 1971.[ 7] INN Tooltip International Nonproprietary Name of DOB,brolamfetamine , was proposed and recommended by theWorld Health Organization (WHO) in 1986.[ 23] [ 24] Multidisciplinary Association for Psychedelic Studies (MAPS) was founded.[ 25] anorexic " (appetite suppressant).[ 26]
Society and culture [ edit ] Internationally, DOB is a Schedule I substance under theConvention on Psychotropic Substances and the drug is legal only for medical, industrial or scientific purposes.[ 27]
Listed as aSchedule 1 as it is an analogue of amphetamine.[ 28]
DOB is considered a Schedule 9 prohibited substance in Australia under thePoisons Standard (February 2017).[ 29] [ 29]
Schedule I, possession of at least 10 mg is a criminal offence.[ 30]
DOB is aClass A drug in the United Kingdom under theMisuse of Drugs Act 1971 .
DOB is aSchedule I controlled substance under federal law in theUnited States .[ 31] [ 32]
^ Anvisa (24 July 2023)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 25 July 2023).Archived from the original on 2023-08-27. Retrieved2023-08-27 .^ World Health Organization (2000).International Nonproprietary Names (INN) for Pharmaceutical Substances ISBN 978-0-11-986227-0 ^a b c d e f g h i Shulgin A (1981)."Profiles of Psychedelic Drugs: 10. DOB" .J Psychoactive Drugs .13 (1): 99.doi :10.1080/02791072.1981.10471457 .PMID 7277091 . Archived fromthe original on 2025-07-12. ^a b c Ray TS (February 2010)."Psychedelics and the human receptorome" .PLOS ONE .5 (2) e9019.Bibcode :2010PLoSO...5.9019R .doi :10.1371/journal.pone.0009019 PMC 2814854 PMID 20126400 . ^a b c d Rudin D, Luethi D, Hoener MC, Liechti ME (2022)."Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues" .The FASEB Journal .36 (S1) fasebj.2022.36.S1.R2121.doi :10.1096/fasebj.2022.36.S1.R2121 ISSN 0892-6638 . ^a b c d e Erowid Online Books: "PiHKAL" - #62 DOB ^a b Shulgin AT, Sargent T, Naranjo C (1971)."4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog" .Pharmacology .5 (2):103– 107.doi :10.1159/000136181 .PMID 5570923 .S2CID 46844380 . ^a b Bowen JS, Davis GB, Kearney TE, Bardin J (March 1983). "Diffuse vascular spasm associated with 4-bromo-2,5-dimethoxyamphetamine ingestion".JAMA .249 (11):1477– 1479.doi :10.1001/jama.1983.03330350053028 .PMID 6827726 . ^ "PDSP Database" .UNC (in Zulu). Retrieved2025-02-04 .^ Liu T."BindingDB BDBM50005257 (+)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+/-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine::2-(2-Methoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((R)-(-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((S)-(+)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[R(-)DOB]::2-(5-Bromo-2,4-dimethoxy-phenyl)-1-methyl-ethylamine::Brolamfetamine::CHEMBL6607::DOB::Racemic DOB" .BindingDB . Retrieved2025-02-04 . ^ van Wijngaarden I, Soudijn W (1997). "5-HT2A, 5-HT2B and 5-HT2C receptor ligands".Pharmacochemistry Library . Vol. 27. Elsevier. pp. 161– 197.doi :10.1016/s0165-7208(97)80013-x .ISBN 978-0-444-82041-9 ^ Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP (June 2002)."Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors" .Br J Pharmacol .136 (4):510– 519.doi :10.1038/sj.bjp.0704747 .PMC 1573376 PMID 12055129 . ^ Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M (2023)."Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors" .Frontiers in Pharmacology .14 1101290.doi :10.3389/fphar.2023.1101290 PMC 9902381 PMID 36762110 . ^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019)."Amphetamine Derivatives as Monoamine Oxidase Inhibitors" .Front Pharmacol .10 1590.doi :10.3389/fphar.2019.01590 PMC 6989591 PMID 32038257 . ^ Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M (December 1997)."Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships" .Biochem Pharmacol .54 (12):1361– 1369.doi :10.1016/s0006-2952(97)00405-x .PMID 9393679 . ^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023)."Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential" .Nat Commun .14 (1) 8221.Bibcode :2023NatCo..14.8221W .doi :10.1038/s41467-023-44016-1 .PMC 10724237 PMID 38102107 . ^a b Lewin AH, Miller GM, Gilmour B (December 2011)."Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class" .Bioorganic & Medicinal Chemistry .19 (23):7044– 7048.doi :10.1016/j.bmc.2011.10.007 .PMC 3236098 PMID 22037049 . ^a b Kramer HK, Poblete JC, Azmitia EC (September 1997). "Activation of protein kinase C (PKC) by 3,4-methylenedioxymethamphetamine (MDMA) occurs through the stimulation of serotonin receptors and transporter".Neuropsychopharmacology .17 (3):117– 129.doi :10.1016/S0893-133X(97)00026-2 .PMID 9272479 . ^a b Kenneth H (1996)."Evidence for the involvement of the serotonin uptake transporter and the serotonin-2 receptor in the activation of protein kinase C (PKC) by substituted amphetamines in the adult rodent brain" .ProQuest . New York University. Retrieved2025-02-01 .MDMA manifests its acute psychotropic and neurotoxic effects by releasing 5-HT from nerve endings. MDMA also shows a moderate agonist-like affinity (1.5-3.2 mM [(sic)]) for the central 5-HT2 receptor. Activation of this receptor stimulates the translocation/activation of protein kinase C (PKC) and the release of Ca2+ from intracellular sequestration sites. MDMA has already been shown to increase [Ca2+], and this may proceed through the activation of this receptor. [...] In vivo, both MDMA and PCA were found to produce a lasting translocation of [protein kinase C (PKC)] in the cortex and hippocampus of treated rats. Fluoxetine, a 5-HT uptake inhibitor, prevents PKC translocation, while ketanserin, a 5-HT2A antagonist, acts similarly but a diminished efficacy. Non-neurotoxic drugs like fluoxetine, DOB, and cocaine were devoid of MDMA's long-term PKC translocating abilities, and suggests that receptor stimulation alone is not the sole mechanism. In synaptosomes, MDMA was effective at producing PKC translocation by binding to the 5-HT uptake carner. This in vitro response [of] fluoxetine reverses this response and demonstrates that MDMA translocates PKC within the 5-HT nerve terminal. ^ Morrison TR, Melloni RH (2014). "The role of serotonin, vasopressin, and serotonin/vasopressin interactions in aggressive behavior".Neuroscience of Aggression . Curr Top Behav Neurosci. Vol. 17. pp. 189– 228.doi :10.1007/7854_2014_283 .ISBN 978-3-662-44280-7 PMID 24496652 .Another 5HT2A receptor partial agonist, DOB, has a marginally higher affinity for the 5HT2A receptor (in its low affinity state) than DOI (Roth et al. 1997), and in the water competition (WC) test it has been shown to block defensive aggression in rats. Interestingly, DOI also reduced the number of offensive aggressive behaviors (i.e., attacks, greater latency to first attack, shorter attack duration) in the same animals that exhibited DOI-induced reductions in defensive behaviors during the WC test (Muehlenkamp et al. 1995). ^ Muehlenkamp F, Lucion A, Vogel WH (April 1995). "Effects of selective serotonergic agonists on aggressive behavior in rats".Pharmacology Biochemistry and Behavior .50 (4):671– 674.doi :10.1016/0091-3057(95)00351-7 .PMID 7617717 .S2CID 12774131 . ^ Parrish JC, Braden MR, Gundy E, Nichols DE (December 2005)."Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists" .Journal of Neurochemistry .95 (6):1575– 1584.doi :10.1111/j.1471-4159.2005.03477.x PMID 16277614 .S2CID 24005602 . ^ "INN Proposed List 55" .World Health Organization (WHO) . 9 April 1986. Retrieved2024-11-03 .^ "INN Recommended List 26" .World Health Organization (WHO) . 9 June 1986. Retrieved2024-11-03 .^ Emerson A, Ponté L, Jerome L, Doblin R (2014)."History and future of the Multidisciplinary Association for Psychedelic Studies (MAPS)" .J Psychoactive Drugs .46 (1):27– 36.doi :10.1080/02791072.2014.877321 .PMID 24830183 . ^ World Health Organization (2024)."Use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances, 2024" (PDF) . World Health Organization. pp. 152– 153. Retrieved2024-10-21 . ^ "List of psychotropic substances under international control" (PDF) . Archived fromthe original (PDF) on 2007-03-02. Retrieved2007-03-30 .^ "(15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine)" .Isomer Design . Archived fromthe original on 2021-11-23.^a b Department of Health and Aged Care (October 2015)."Poisons Standard" .Federal Register of Legislation . Australian Government. ^ "Об утверждении значительного, крупного и особо крупного размеров наркотических средств и психотропных веществ, а также значительного, крупного и особо крупного размеров для растений, содержащих наркотические средства или психотропные вещества, либо их частей, содержащих наркотические средства или психотропные вещества, для целей статей 228, 228.1, 229 и 229.1 Уголовного кодекса Российской Федерации" [On approval of significant, large and especially large sizes of narcotic drugs and psychotropic substances, as well as significant, large and especially large sizes for plants containing narcotic drugs or psychotropic substances, or their parts containing narcotic drugs or psychotropic substances, for the purposes of Articles 228, 228.1, 229 and 229.1 of the Criminal Code of the Russian Federation].Постановление Правительства РФ от 01.10.2012 N 1002 [Resolution of the Government of the Russian Federation of 01.10.2012 N 1002 ] (in Russian).^ Shulgin A, Manning T, Daley PF (2011).The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds ISBN 978-0-9630096-3-0 ^ Bartels Jr JR (14 September 1973)."Part 308 – Schedules of Controlled Substances; Additions to Schedule I" (PDF) .Federal Register . Vol. 38, no. 183.Drug Enforcement Administration . Archived fromthe original (PDF) on 2022-03-03. Retrieved2023-09-30 – via Isomer Design.
Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. 2,N ,N -TMT 4,N ,N -TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N ,N -TMT 7,N ,N -TMT 5-MeO-2,N ,N -TMT 5-MeO-4,N ,N -TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET) α-Alkyltryptamines 5-Methoxy-α-alkyltryptamines: 5-MeO-AET α,N ,N -TMT (α-Me-DMT; Alpha-N) 5-MeO-AMT (α,O -DMS; Alpha-O) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) 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-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: 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 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 CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )mCPP 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 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,clorotepine ,clozapine ,fluperlapine ,olanzapine ,risperidone ,sertindole ,tiospirone ,ziprasidone ,zotepine )Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148) ,amesergide ,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,imipramine )Typical antipsychotics (e.g.,acetophenazine ,chlorpromazine ,chlorprothixene ,fluphenazine ,loxapine ,pimozide )Vortioxetine
TAAR1 Tooltip Trace amine-associated receptor 1
TAAR5 Tooltip Trace amine-associated receptor 5
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the
List of trace amines ,
TAAR , and
TAAR1 pages.
See also: Receptor/signaling modulators
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 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 )
