Chemical compound
Pharmaceutical compound
α-Methyltryptamine Clinical data Trade names Indopan; Indopane Other names alpha -Methyltryptamine; αMT; α-ET; AMT; IT-290; IT-403 ((+)-αMT); NSC-97069; PAL-17;[ 1] Routes of Oral ,insufflation ,rectal ,smoked ,IM ,IV [ 2] Drug class Entactogen ;Stimulant ;Psychedelic ;Hallucinogen ;Monoamine releasing agent ;Serotonin receptor agonist ;Monoamine oxidase inhibitor ATC code Legal status Legal status Pharmacokinetic dataOnset of action 3–4 hours[ 4] Duration of action 12–24 hours[ 4] Identifiers CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.005.522 Chemical and physical data Formula C 11 H 14 N 2 Molar mass −1 3D model (JSmol ) InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
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α-Methyltryptamine (αMT ,AMT ) is apsychedelic ,stimulant , andentactogen drug of thetryptamine family.[ 5] [ 6] antidepressant atUpjohn in the 1960s, and was used briefly as an antidepressant in theSoviet Union under the brand nameIndopan orIndopane before being discontinued.[ 4] [ 7] [ 8]
Side effects of αMT includeagitation ,restlessness ,confusion ,lethargy ,pupil dilation ,jaw clenching , andrapid heart rate , among others.[ 4] [ 9] releasing agent of serotonin, norepinephrine, and dopamine , as aserotonin receptor agonist , and as a weakmonoamine oxidase inhibitor .[ 1] substituted tryptamine and is closely related toα-ethyltryptamine (αET) and otherα-alkylated tryptamines .[ 1] [ 5]
αMT appears to have first been described by at least 1929.[ 10] [ 11] antidepressant in theSoviet Union in the 1960s.[ 4] [ 12] [ 9] [ 13] [ 14] recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported.[ 4] [ 13] [ 9] [ 12] controlled substance in various countries, including theUnited States .[ 13] [ 4]
Under the brand name Indopan or Indopane, αMT at doses of 5 to 10 mg was used for anantidepressant effect.[medical citation needed
With 20 to 30 mg,euphoria ,empathy , andpsychedelic effects become apparent and can last as long as 12 hours.[ 15] mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 hours. Users report that αMT infreebase form issmoked , with doses between and 2 and 5 mg.[ 2] [unreliable source? [ 5]
Neurologic side effects of αMT includeagitation ,restlessness ,confusion , andlethargy .[ 4] [ 9] vomiting ,mydriasis (pupillary dilation),jaw clenching ,tachycardia ,salivation ,diaphoresis (sweating), andelevations in blood pressure ,temperature , andrespiratory rate .[ 4] [ 9]
Side effects self-reported by recreational users includeanxiety ,muscle tension ,jaw tightness ,pupil dilation ,tachycardia ,headaches ,nausea , andvomiting , as well aspsychedelic effects including visual hallucinations and an altered state of mind.[ 5] [ 16]
αMT is capable of causing life-threatening side effects includinghyperthermia ,hypertension , andtachycardia .[ 9] [ 17] [ 18] Miami-Dade county and a British teenager, both of whom died after consuming 1 g of αMT.[ 19] [ 9]
αMT acts as a relatively balancedreuptake inhibitor andreleasing agent of the main threemonoamines ;serotonin ,norepinephrine , anddopamine ,[ 20] selective serotonin receptor agonist .[ 21]
Activities of αMT and related compounds Compound Monoamine release (EC50 Tooltip half-maximal effective concentration , nM)5-HT2A receptor agonism Serotonin Dopamine Norepinephrine EC50 Tooltip half-maximal effective concentration (nM)Emax (%)Tryptamine 33 164 716 7.4 104 Serotonin 44 >10,000 >10,000 ND ND N ,N -DMT114 >10,000 4,166 38 83 αMT 22–68 79–112 79–180 23 103 αET 23 232 640 (Emax Tooltip maximal efficacy = 78%) >10,000 21 5-MeO-αMT 460 8,900 1,500 2.0–8.4 ND MDMA 57 376 77 ND ND Notes: The smaller the value, the more strongly the compound produces the effect.Refs: [ 22] [ 1] [ 23] [ 24] [ 25]
Monoamine oxidase inhibition [ edit ] αMT has been shown as areversible inhibitor of theenzyme monoamine oxidase (MAO)in vitro [ 26] in vivo [ 27] harmaline at equimolar doses.[ note 1] 5-hydroxytryptophan -induced rise of serotonin at any level.[ 28] IC50 Tooltip half-maximal inhibitory concentration of αMT for inhibition of MAO-A has been found to be 380 nM.[ 29] para -methoxyamphetamine4-methylthioamphetamine (4-MTA).[ 30]
Serotonergic neurotoxicity [ edit ] A closeanalogue of αMT,α-ethyltryptamine (αET), is known to be aserotonergic neurotoxin similarly toMDMA andpara -chloroamphetamine[ 31] [ 22] [ 32]
2-Oxo-αMT, 6-hydroxy-αMT, 7-hydroxy-αMT, and 1′-hydroxy-αMT were detected asmetabolites of αMT in maleWistar rats .[ 4] [ 33] [ 34]
αMT is asynthetic substituted tryptamine with amethyl substituent at thealpha carbon .[ 1] [ 9] substrate formonoamine oxidase A , thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system. Its chemical relation to tryptamine is analogous to that ofamphetamine tophenethylamine , amphetamine being α-methylphenethylamine.[ 9] neurotransmitter serotonin (5-hydroxytryptamine) which partially explains itsmechanism of action .
Manyanalogues of αMT are known, includingα-ethyltryptamine (αET),4-methyl-αMT ,5-chloro-αMT (PAL-542),5-fluoro-αMT (PAL-544),5-fluoro-αET (PAL-545),5-methoxy-αMT (5-MeO-αMT),α,N -dimethyltryptamine (α,N -DMT;N -methyl-αMT),α,N ,N -trimethyltryptamine (α,N ,N -TMT;N -dimethyl-αMT),α-methylserotonin (α-methyl-5-HT; 5-hydroxy-αMT), andindolylpropylaminopentane (IPAP; α,N -dipropyltryptamine or α,N -DPT), among others.[ 1] [ 5] keto andN -methylated derivative BK-NM-AMT .[ 35] [ 36] [ 37]
α-Methyltryptophan , aprodrug ofα-methylserotonin , alsometabolizes into αMT, but only in small amounts.[ 38] [ 39] [ 40]
The synthesis of αMT can be accomplished through several different routes, the two most widely known being the nitroaldol condensation betweenindole-3-carboxaldehyde andnitroethane underammonium acetate catalysis which produces 1-(3-indolyl)-2-nitropropene-1, the product can subsequently be reduced using a reducing agent likelithium aluminum hydride [ 41] hydroxylamine .[citation needed , followed by reduction of the obtained ketoxime withlithium aluminum hydride .[ 5]
αMT has been said to have been firstsynthesized in 1947, alongsideα-ethyltryptamine (αET).[ 12] [ 22] [ 42] scientific literature by at least 1929.[ 10] [ 11] antagonist ofergotamine at this time.[ 10] [ 11]
αMT started to be more intensively studied, along with αET, in the late 1950s and early 1960s.[ 12] [ 43] [ 44] [ 45] [ 28] [ 46] [ 47] [ 48] [ 49] [ 50] Upjohn (code name U-14,164E) andSandoz (code name IT-290) as a possiblepharmaceutical drug and was simultaneously marketed in theSoviet Union as anantidepressant under the brand name Indopan or Indopane in the 1960s.[ 13] [ 14] [ 9] [ 51] withdrawn .[ 14]
αMT started being used as arecreational drug in the 1960s[ 9] designer drug increased in the 1990s.[ 13] controlled substance in theUnited States in 2003.[ 13]
Society and culture [ edit ] αMT never received a formalgeneric name .[ 52] scientific literature , it has been referred to asα-methyltryptamine oralpha-methyltryptamine (abbreviated asα-MT ,αMT , orAMT ).[ 13] [ 14] IT-290 (Sandoz ),[ 53] NSC-97069 ,[ 12] PAL-17 ,[ 1] Ro 3-0926 ,[ 54] [ 55] U-14,164E (Upjohn ).[ 56] [ 57] [ 12] [ 9] Soviet Union , the drug was merely referred to by its brand nameIndopan orIndopane .[ 58] [ 9] 3-(2-aminopropyl)indole and3-IT .[ 12] IT-403 .[ 12] [ 9]
The 5-methoxy analogue,5-MeO-αMT isschedule 9 in Australia and αMT would be controlled as an analogue of this.[ 59]
αMT is placed under Austrian law (NPSG) Group 6.[ 60]
Canada has no mention of αMT in theControlled Drugs and Substances Act .[ 61]
As of October 2015 αMT is a controlled substance in China.[ 62]
In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).[ 60]
AMT, alfa-methyltryptamine, is a controlled drug in Finland.[ 63]
αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[ 60]
αMT was controlled on the Schedule C list in Hungary in 2013.[ 60]
In Lithuania (2012), αMT is controlled as a tryptamine derivative put under control in the 1st list of Narcotic Drugs and Psychotropic Substances which use is prohibited for medical purposes.[ 60]
αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[ 60]
αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[ 60]
αMT is legal in Spain.[ 64]
Sveriges riksdags Statens folkhälsoinstitut Lagen om förbud mot vissa hälsofarliga varor Act on the Prohibition of Certain Goods Dangerous to Health ) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT), making it illegal to sell or possess.[ 65]
αMT was made illegal in the United Kingdom as of 7 January 2015, along with5-MeO-DALT .[ 66] Advisory Council on the Misuse of Drugs recommended that αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.[ 67]
TheDrug Enforcement Administration (DEA) placed αMT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, αMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).[ 68]
Besidesdepression , αMT has been studied in people withschizophrenia and other conditions.[ 1]
^ MAOI potency was comparable at 7 μM/kg, equivalent to 1.5 mg/kg of Harmaline and 1.2 mg/kg of αMT. At 70 μM/kg αMT was a much less effective MAOI than harmaline.[ 28] ^a b c d e f g h Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014)."Alpha-ethyltryptamines as dual dopamine-serotonin releasers" .Bioorganic & Medicinal Chemistry Letters .24 (19):4754– 4758.doi :10.1016/j.bmcl.2014.07.062 .PMC 4211607 PMID 25193229 . ^a b Dialtonez (12 March 2003)."AMT FAQ" .Erowid Vault . ^ Anvisa (2023-07-24)."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 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27 .^a b c d e f g h i j Barceloux DG (20 March 2012).Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants 196– 199.ISBN 978-0-471-72760-6 ^a b c d e f "#48 a-MT" .Erowid Online Books: TIHKAL .^ "AMT (alpha-methyltryptamine)" .Erowid Vault .^ Iversen L (11 November 2013).Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man ISBN 978-1-4613-4045-4 ^ Halberstadt AL, Geyer MA (17 May 2013)."Neuropharmacology of lysergic acid diethylamide (LSD) and other hallucinogens." . In Miller PM, Ball SA, Bates ME, Blume AW, Kampman KM, Kavanagh DJ, Larimer ME, Petry NM, De Witte P (eds.).Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders . Vol. 2. Academic Press. pp. 625–635 (632).doi :10.1016/B978-0-12-398335-0.00061-3 .ISBN 978-0-12-398360-2 ^a b c d e f g h i j k l m n Boland DM, Andollo W, Hime GW, Hearn WL (July–August 2005)."Fatality due to acute alpha-methyltryptamine intoxication" .Journal of Analytical Toxicology .29 (5):394– 397.doi :10.1093/jat/29.5.394 PMID 16105268 .α-Methyltryptamine (AMT) is a synthetic drug of the tryptamine family. It is an indole analogue of amphetamine initially investigated as a monoamine oxidase inhibitor. In the 1960s, the Soviet Union marketed AMT as an antidepressant under the name of Indopan. During the same period, Sandoz (as IT-290 and IT-403) and the Upjohn Company (as [U-14,164E]) studied AMT and its commercial use as a stimulant, but found it to be of little medicinal value. Although clinical use of AMT is obsolete today, recreational use has gained popularity because of the intense hallucinogenic properties lasting up to 16 h. To illustrate recreational use of AMT in the 1960s, Alexander Shulgin, in his book TiHKAL, references the author Ken Kesey and his experiences with AMT and other hallucinogenic drugs (1). ^a b c Gaddum JH, Hameed KA (June 1954)."Drugs which antagonize 5-hydroxytryptamine" .British Journal of Pharmacology and Chemotherapy .9 (2):240– 248.doi :10.1111/j.1476-5381.1954.tb00848.x .PMC 1509436 PMID 13172437 .The antagonism of ergotoxine and tryptamine was described by Laidlaw (1911) and that of ergotamine and α-methyltryptamine by Seki (1929). ^a b c Seki J (1929)."Pharmakologische Untersuchungen des α-Methyl-β-indoläthylamins" [Pharmacological studies of α-methyl-β-indoleethylamine].Japanese Journal of Medical Sciences. Part 4: Pharmacology .3 . National Research Council of Japan:235– 285.ISSN 0368-3745 .OCLC 610325817 . ^a b c d e f g h Elliott SP, Brandt SD, Freeman S, Archer RP (March 2013). "AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis".Drug Testing and Analysis .5 (3):196– 202.doi :10.1002/dta.1420 .PMID 23042766 .α-Methyltryptamine (2, 3-(2-aminopropyl)indole, AMT, α-MT, 3-IT, IT-290, IT-403, U-14, 162-E, Ro 3-0926, NSC 97069, Indopan; Figure 1), on the other hand, is a positional isomer of 5-IT that also shows long-lasting psychoactive effects in humans[1] although further studies are needed to determine the differences or similarities between both psychopharmacological profiles. Following its first synthesis in 1947,[5] the interest in AMT, and other α-alkylated tryptamines, began to develop in the late 1950s when it was discovered that some of these analogues also displayed monoamine oxidase (MAO) inhibiting properties.[6,7] [...] ^a b c d e f g Araújo AM, Carvalho F, Bastos Md, Guedes de Pinho P, Carvalho M (August 2015). 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SSRIs Tooltip Selective serotonin reuptake inhibitors SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors NRIs Tooltip Norepinephrine reuptake inhibitors NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants SARIs Tooltip Serotonin antagonist and reuptake inhibitors SMS Tooltip Serotonin modulator and stimulators Others
TCAs Tooltip Tricyclic antidepressants TeCAs Tooltip Tetracyclic antidepressants Others
Non-selective MAOA Tooltip Monoamine oxidase A -selectiveMAOB Tooltip Monoamine oxidase B -selective
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 Others Cyclized Ergolines /lysergamides (e.g.,LSD )Harmala alkaloidsβ-carbolines (e.g.,harmine ,harmaline )Iboga alkaloids18-MAC ,18-MC ,coronaridine ,ibogaine ,ibogamine ,ME-18-MC ,noribogaine ,tabernanthine ,voacangine )Ibogalogs (e.g.,ibogainalog )Partial ergolines (e.g.,NDTDI ,RU-28306 ,DEIMDHPCA ,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 )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF ,dimemebfe (5-MeO-BFE) ,mebfap )Benzothiophenes (e.g.,3-APBT )Indazoles (e.g.,AL-38022A ,O -methyl-AL-34662Indenes (e.g.,C-DMT )Isotryptamines (e.g.,6-MeO-isoDMT ,Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g.,mefloquine )
Phenethylamines
25x-NB (NBOMes) 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 4C-x Cyclized 1-Aminomethylindanes (e.g.,2CB-Ind ,jimscaline )2-Aminoindanes (e.g.,DOM-AI )2-Aminotetralins (e.g.,DOM-AT )3-Phenylpiperidines (e.g.,LPH-5 ,LPH-48 )Benzazepines (e.g.,lorcaserin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )DMBMPP (juncosamine) Ergolines /lysergamides (e.g.,LSD )Glaucine IHCH-7113 Partial ergolines (e.g.,NDTDI ,DEIMDHPCA ,DEMPDHPCA ,DEMTMPDHPCA ,DEMNDHPCA )Phenylcyclopropylamines (e.g.,DMCPA ,TMT )Phenylmorpholines (phenmetrazines) (e.g.,2C-B-morpholine )Phenyloxazolamines (aminorexes ) (e.g.,2C-B-aminorex )Z3517967757 ZC-B DOx FLY MDxx Scalines 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-2 ,F-22 )Benzothiophenes (e.g.,5-APBT ,6-APBT )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 ,TMA-6 )TOMSO ZDCM-04
Lysergamides Others 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)
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
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) Bupropion Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Hydroxybupropion 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
Tryptamines 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 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-DiPT 5-HO-NiPT 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 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 Triptans Cyclized tryptamines Barettin Bufothionine Ciclindole Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD )Flucindole Frovatriptan Harmala alkaloidsβ-carbolines (e.g.,6-MeO-THH ,9-Me-BC ,β-carboline (norharman) ,harmaline ,harmalol ,harmane ,harmine ,pinoline ,tetrahydroharmine ,tryptoline )Iboga alkaloidsibogaine ,ibogamine ,noribogaine ,tabernanthine )Ibogalogs (e.g.,ibogainalog ,ibogaminalog (DM-506) ,noribogainalog ,tabernanthalog )Imidazolylindoles (e.g.,AGH-107 ,AGH-192 ,AH-494 )LY-266,097 LY-344864 Metralindole O -MethylnordehydrobufoteninePartial ergolines and lysergamides (e.g.,NDTDI ,RU-27849 ,RU-28251 ,RU-28306 ,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 )PHA-57378 Piperidinylethylindoles (e.g.,Pip-T ,indolylethylfentanyl )PNU-22394 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-135807 ,eletriptan )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 )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 Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,5-MeO-DiBF ,BPAP ,3-F-BPAP ,dimemebfe ,mebfap )Benzothiophenes (e.g.,3-APBT )CP-94253 CT-4436 Daledalin Gramine Histamine I-32 IAL IN-399 Indazoles (e.g.,AL-34662 ,AL-38022A ,O -methyl-AL-34662VU6067416 ,YM-348 )Indenes (e.g.,C-DMT )Indolizines (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 Latrepirdine Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan ,LY-334370 ,naratriptan ) Phenethylamines (e.g.,phenethylamine ,amphetamine )Piperidinylindoles (e.g.,BRL-54443 ,LY-334370 ,naratriptan ,sertindole ,SN-22 )Pirlindole Pyridinylindoles (e.g.,tepirindole )Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA) ,3-pyrrolylethylamine (3-NEA) ,3-pyrrolylpropylamine )Quinolinylethylamines (e.g.,mefloquine )(R )-69 (3IQ) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088 ,LY-367265 ,RU-24,969 )Tetrindole Tiflucarbine Tipindole Zilpaterol (RU-42173)
