Chemical compound
α-Methyltryptamine Other names Indopan; α-Methyl-3-indoleethanamine; 3-(2-Aminopropyl)indole; IT-290, IT-403, U-14,164E, 3-IT[ 1] Routes of administration Oral , Insufflation , Rectal , Smoked , IM , IV [ 1] ATC code Legal status
1-(1H -Indol-3-yl)propan-2-amine
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.005.522 Formula C 11 H 14 N 2 Molar mass 174.247 g·mol−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
Y Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N
Y
(verify)
α-Methyltryptamine (abbreviated as αMT , AMT ) is a psychedelic , stimulant , and entactogen drug of the tryptamine class.[ 3] [ 4] It was originally developed as an antidepressant by chemists at Upjohn in the 1960s,[ 5] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.[ 6] [ 7] [ 8]
αMT is a tryptamine with a methyl substituent at the alpha carbon . This alpha substitution makes it a relatively poor substrate for monoamine 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 of amphetamine to phenethylamine , amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action .
The synthesis of αMT can be accomplished through several different routes, the two most widely known being the Nitroaldol Condensation between Indole-3-carboxaldehyde and nitroethane under ammonium acetate catalysis which produces 1-(3-indolyl)-2-nitropropene-1 , the product can subsequently be reduced using a reducing agent like lithium aluminum hydride [ 9] It's also hypothesized that it can be reduced using Copper(II) chloride and Sodium borohydride . The alternative synthesis is the condensation between indole-3-acetone and Hydroxylamine [citation needed ] , followed by reduction of the obtained ketoxime with lithium aluminum hydride .[ 10]
αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines ; serotonin , norepinephrine , and dopamine ,[ 11] and as a non-selective serotonin receptor agonist .[ 12]
αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro [ 13] and in-vivo .[ 14]
In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[ note 1] Dextroamphetamine did not enhance the 5-hydroxytryptophan -induced rise of serotonin at any level.[ 15]
A close analogue of αMT, α-ethyltryptamine (αET), is known to be a serotonergic neurotoxin .[ 16] [ 17] [ 18]
2-Oxo-αMT, 6-hydroxy-αMT,[ 19] 7-hydroxy-αMT and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats
.[ 20]
Under the trade name Indopan, 5-10 milligrams were used for an antidepressant effect.[medical citation needed ]
With 20–30 milligrams, euphoria , empathy , and psychedelic effects become apparent and can last as long as 12 hours.[ 21] A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 hours. Users report that αMT in freebase form is smoked , with doses between and 2 and 5 milligrams.[ 1] [unreliable source? ] [ 3]
Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy. Physical manifestations including vomiting , mydriasis (pupillary dilation), jaw clenching , tachycardia , salivation , diaphoresis (sweating), and elevations in blood pressure , temperature , and respiratory rate .[ 22]
Side effects self-reported by recreational users include anxiety , muscle tension , jaw tightness , pupil dilation , tachycardia , headaches , nausea , and vomiting , as well as psychedelic effects including visual hallucinations and an altered state of mind.[ 3] [ 23]
The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.[ 24]
As of October 2015 αMT is a controlled substance in China.[ 25]
In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).[ 26]
Canada has no mention of αMT in the Controlled Drugs and Substances Act .[ 27]
αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[ 26]
αMT is placed under Austrian law (NPSG) Group 6.[ 26]
αMT was controlled on the Schedule C list in Hungary in 2013.[ 26]
αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[ 26]
αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[ 26]
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.[ 26]
αMT is legal in Spain.[ 28]
Sveriges riksdags health ministry Statens folkhälsoinstitut classified αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated 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.[ 29]
αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT .[ 30]
This was following the events of 10 June 2014 when the 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.[ 31]
The Drug 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).[ 32]
AMT, alfa-methyltryptamine is a controlled drug in Finland[ 33]
αMT is capable of causing life-threatening side-effects including hyperthermia , hypertension , and tachycardia .[ 22] [ 34] Fatalities have been reported in association with high doses or concomitant use of other drugs.[ 35] Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade county and a British teenager, both of whom died after consuming 1g of αMT.[ 36] [ 22]
^ MAOI potency was comparable at 7 μM/kg, equivalent to 1.5mg/kg of Harmaline and 1.2mg/kg of αMT. At 70μM/kg αMT was a much less effective MAOI than harmaline.[ 15]
^ a b c "Erowid AMT Vault : FAQ by Dialtonez" .
^ 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. Retrieved 2023-08-27 .
^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT" .
^ "Erowid AMT (alpha-methyltryptamine) Vault" .
^ US Patent 3296072 , Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co
^ Barceloux DG (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants . John Wiley & Sons. pp. 196–. ISBN 978-0-471-72760-6 .
^ Iversen L (11 November 2013). Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man . Springer Science & Business Media. pp. 132–. ISBN 978-1-4613-4045-4 .
^ Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders . Academic Press. 17 May 2013. pp. 632–. ISBN 978-0-12-398360-2 .
^ Anonymous. "TheHive" . Retrieved 7 June 2023 .
^ Shulgin A. "TIHKAL" . Retrieved 18 May 2018 .
^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology . 559 (2–3): 132–137. doi :10.1016/j.ejphar.2006.11.075 . PMID 17223101 .
^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes" . Biological & Pharmaceutical Bulletin . 30 (12): 2328–2333. doi :10.1248/bpb.30.2328 . PMID 18057721 .
^ Arai Y, Toyoshima Y, Kinemuchi H (June 1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by alpha-methylated substrate-analogue monoamines, alpha-methyltryptamine, alpha-methylbenzylamine and two enantiomers of alpha-methylbenzylamine" . Japanese Journal of Pharmacology . 41 (2): 191–197. doi :10.1254/jjp.41.191 . PMID 3747266 .
^ Greig ME, Walk RA, Gibbons AJ (October 1959). "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo" . The Journal of Pharmacology and Experimental Therapeutics . 127 : 110–115. PMID 13851725 .
^ a b Gey KF, Pletscher A (August 1962). "Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo" . British Journal of Pharmacology and Chemotherapy . 19 (1): 161–167. doi :10.1111/j.1476-5381.1962.tb01437.x . PMC 1482243 . PMID 13898151 .
^ Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy" . J Psychopharmacol . 35 (5): 512–536. doi :10.1177/0269881120920420 . PMC 8155739 . PMID 32909493 .
^ Glennon RA, Dukat MG (December 2023). "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacol Transl Sci . 6 (12): 1780–1789. doi :10.1021/acsptsci.3c00139 . PMID 38093842 .
^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". Eur J Pharmacol . 200 (1): 187–190. doi :10.1016/0014-2999(91)90686-k . PMID 1722753 .
^ Szara S (February 1961). "6-Hydroxylation: an important metabolic route for alpha-methyltryptamine" . Experientia . 17 (2): 76–77. doi :10.1007/BF02171429 . PMID 13774483 . S2CID 27030395 .
^ Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Iwata YT, Inoue H (December 2008). "In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites". Xenobiotica; the Fate of Foreign Compounds in Biological Systems . 38 (12): 1476–1486. doi :10.1080/00498250802491654 . PMID 18982537 . S2CID 20637936 .
^ Wilcox J (2012). "Psychoactive properties of alpha-methyltryptamine: analysis from self reports of users". Journal of Psychoactive Drugs . 44 (3): 274–276. doi :10.1080/02791072.2012.704592 . PMID 23061328 . S2CID 38340985 .
^ a b c 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 .
^ "Erowid AMT Vault : Effects" .
^ "Erowid 5-MeO-AMT Vault : Legal Status" .
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015 .
^ a b c d e f g "Reference at www.who.int" (PDF) .
^ "CSDA" . Archived from the original on 2011-09-28. Retrieved 2011-06-05 .
^ "Medicamentos de Uso Humano - Estupefacientes y Psicótropos" . Agencia Española de Medicamentos y Productos Sanitarios . Archived from the original on 2019-01-02. Retrieved 2019-01-01 .
^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (PDF) , Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26 (in Swedish), February 2005, archived from the original (PDF) on 2013-09-29, retrieved 2013-10-07
^ "The Misuse of Drugs (Amendment No. 3) (England, Wales and Scotland) Regulations 2014" . www.legislation.gov.uk .
^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF) . UK Home Office. p. 12. Retrieved 10 June 2014 .
^ "Alpha-methyltryptamine" (PDF) . DEA Office of Diversion Control . April 2013. Archived (PDF) from the original on 2013-10-17. Retrieved 2013-10-10 .
^ "Reference at www.finlex.fi" (PDF) .
^ Gillman PK (October 2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity" . British Journal of Anaesthesia . 95 (4): 434–441. doi :10.1093/bja/aei210 . PMID 16051647 . "drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers"
^ "Call for ban on drug after reveller's death" . Western Gazette . March 22, 2012. Archived from the original on 2013-10-16. Retrieved October 1, 2013 .
^ "Southampton 'legal high' death deemed 'accidental' " . BBC News . 2013-11-12. Retrieved 2013-11-19 .
Psychedelics (5-HT2A agonists)
Benzofurans Lyserg‐ amides Phenethyl‐ amines
2C-x
3C-x 4C-x DOx HOT-x MDxx Mescaline (subst.) TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
Piperazines Tryptamines
alpha -alkyltryptaminesx -DALT x -DET x -DiPT x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT Ibogaine-related x -MET x -MiPT Others
Others
Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) 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-11,461
F-12826
F-13714
F-14679
F-15063
F-15,599
Flesinoxan
Flibanserin
Flumexadol
Hypidone
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
Oxaflozane
Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24,969
S-14,506
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-92,016-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-7,378
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-649,915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
5-HT1B
Agonists: Anpirtoline
CGS-12066A
CP-93129
CP-94253
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
mCPP
RU-24,969
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-122,288
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-215,840 , 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-215,840 , 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-12,233
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-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Tryptamines
1-Methylpsilocin
2-Me-DET
2-Methyl-5-HT
2,N ,N -TMT
4,5-DHP-DMT
4-AcO-DALT
4-AcO-DET
4-AcO-DiPT
4-AcO-EPT
4-AcO-NMT
4-AcO-MALT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPT
4-HO-MsBT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
5-BT
5-Bromo-DMT
5-CT
5-Chloro-DMT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-DiPT
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
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-MeO-T-NBOMe
5-MeS-DMT
5-Methoxytryptamine (5-MT; mexamine)
5-Methyl-DMT
5-Methyltryptamine
5-MT-NB3OMe
5-(Nonyloxy)tryptamine
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,6-DHT
5,7-DHT
6-Fluoro-DMT
7-Methyl-DMT
Acetryptine (5-AT)
Aeruginascin
AGH-107
AGH-192
AH-494
ALiPT
Baeocystin
Benzotript
Bufotenidine
Bufotenin (5-HO-DMT)
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DMT
DPT
E-6801
E-6837
EiPT
EMDT
EPT
Ethocybin
FGIN-127
FGIN-143
FT-104
HIOC
Idalopirdine
Indolylethylfentanyl
Indorenate
Iprocin (4-HO-DiPT)
Lespedamine
MET
Methylbutyltryptamine
Miprocin (4-HO-MiPT)
MiPT
MPT
Milipertine
MS-245
MSBT
N -Feruloylserotonin (moschamine)
NET
NMT
Norbaeocystin
NTBT
O-4310
Oxypertine
PiPT
Psilacetin (O -acetylpsilocin; 4-AcO-DMT)
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
Serotonin (5-HT)
Solypertine
ST-1936
Tryptamine
Tryptophan
Yuremamine
Z2876442907
N -Acetyltryptaminesα-Alkyltryptamines Triptans Cyclized tryptamines
Bay R 1531
Ciclindole
Cyclic 3-OHM
Ergolines and lysergamides (e.g., LSD )
Flucindole
Harmala alkaloids and β-carbolines (e.g., harmaline , 6-MeO-THH )
Iboga alkaloids (e.g., ibogaine , ibogamine , noribogaine , tabernanthine )
Metralindole
NDTDI
RU-28306
Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine )