Elopiprazole

Elopiprazole
Systematic (IUPAC) name

1-(1-benzofuran-7-yl)-4-{[5-(4-fluorophenyl)-1H-pyrrol-2-yl]methyl}piperazine
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Registry Number	115464-77-2
ATC code	None
PubChem	CID 208917
ChemSpider	181013
UNII	419A0R564U^Y
Chemical data
Formula	C₂₃H₂₂F N₃O
Molecular mass	375.44 g/mol
SMILES Fc1ccc(cc1)c2ccc(n2)CN5CCN(c4cccc3c4occ3)CC5

Elopiprazole is an antipsychotic drug of the phenylpiperazine class which was never marketed.^[1] It is similar in chemical structure to aripiprazole.

References

↑ van Wijngaarden I, Kruse CG, van Hes R, van der Heyden JA, Tulp MT (November 1987). "2-Phenylpyrroles as conformationally restricted benzamide analogues. A new class of potential antipsychotics. 1". Journal of Medicinal Chemistry 30 (11): 2099–104. doi:10.1021/jm00394a028. PMID 2889830.

Antipsychotics (neuroleptics) (N05A)

Typical

Benzamides: Levosulpiride; Nemonapride; Sulpiride; Sultopride; Tiapride; Veralipride

Butyrophenones: Azaperone; Benperidol; Bromperidol; Droperidol; Fluanisone; Haloperidol #; Lenperone; Moperone; Pipamperone; Spiperone; Timiperone; Trifluperidol

Diphenylbutylpiperidines: Clopimozide; Fluspirilene; Penfluridol; Pimozide

Phenothiazines: Acepromazine; Acetophenazine; Butaperazine; Carphenazine; Chloracizine; Chlorproethazine; Chlorpromazine; Cyamemazine; Dixyrazine; Fluacizine; Fluphenazine; Levomepromazine/Methotrimeprazine; Mesoridazine; Perazine; Periciazine; Perphenazine; Piperacetazine; Pipotiazine; Prochlorperazine; Promazine; Promethazine; Propiomazine; Sulforidazine; Thiethylperazine; Thiopropazate; Thioproperazine; Thioridazine; Trifluoperazine; Triflupromazine

Thioxanthenes: Chlorprothixene; Clopenthixol; Flupentixol; Thiothixene; Zuclopenthixol

Tricyclics: Butaclamol; Fluotracen; Loxapine; Trimipramine

Others: Prothipendyl

Atypical

Benzamides: Amisulpride; Remoxipride‡

Butyrophenones: Cinuperone; Melperone; Setoperone

Benzo(iso)oxazole piperidines: Iloperidone; Ocaperidone; Paliperidone; Risperidone #

Benzo(iso)thiazole piperazines: Lurasidone; Perospirone; Revospirone; Tiospirone; Ziprasidone

Diphenylbutylpiperazines: Amperozide

Phenylpiperazines: Aripiprazole; Bifeprunox; Brexpiprazole^†

Tricyclics: Amoxapine; Asenapine; Carpipramine; Clocapramine; Clorotepine; Clotiapine; Clozapine #; Fluperlapine; Metitepine; Mosapramine; Olanzapine; Quetiapine; Tenilapine; Zotepine

Others: Blonanserin; Cariprazine; Molindone; Pimavanserin; Sertindole; Zicronapine^†

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Index of psychology and psychiatry

Description	Mental processes

Disorders	Mental and behavioral ADHD OCD Tourette's Mood Developmental pervasive dyslexia and specific Substance-related alcohol Emotional and behavioral Symptoms and signs eponymous Evaluation and testing

Treatment	Psychotherapy CBT Drugs depression antipsychotics anxiety dementia hypnotics and sedatives psychostimulants, ADHD and nootropics

Dopaminergics

Receptor ligands

Agonists: Adamantanes: Amantadine
Memantine
Rimantadine; Aminotetralins: 7-OH-DPAT
8-OH-PBZI
Rotigotine
UH-232; Benzazepines: 6-Br-APB
Fenoldopam
SKF-38,393
SKF-77,434
SKF-81,297
SKF-82,958
SKF-83,959; Ergolines: Bromocriptine
Cabergoline
Dihydroergocryptine
Epicriptine
Lisuride
LSD
Pergolide; Dihydrexidine derivatives: 2-OH-NPA
A-86929
Adrogolide (ABT-431, DAS-431)
Ciladopa
Dihydrexidine
Dinapsoline
Dinoxyline
Doxanthrine; Others: A-68930
A-77636
A-412997
ABT-670
ABT-724
Aplindore
Apomorphine
Aripiprazole
Bifeprunox
BP-897
Captodiame
CY-208,243
Dizocilpine
Etilevodopa
Flibanserin
Ketamine
Melevodopa
Modafinil
Pardoprunox
Phencyclidine
PD-128,907
PD-168,077
PF-219,061
Piribedil
Pramipexole
Propylnorapomorphine
Pukateine
Quinagolide
Quinelorane
Quinpirole
RDS-127
Ro10-5824
Ropinirole
Rotigotine
Roxindole
Salvinorin A
SKF-89,145
Sumanirole
Terguride
Umespirone
WAY-100,635

Antagonists: Typical antipsychotics: Acepromazine
Azaperone
Benperidol
Bromperidol
Clopenthixol
Chlorpromazine
Chlorprothixene
Droperidol
Flupentixol
Fluphenazine
Fluspirilene
Haloperidol
Levosulpiride
Loxapine
Mesoridazine
Methotrimeprazine
Nemonapride
Penfluridol
Perazine
Periciazine
Perphenazine
Pimozide
Prochlorperazine
Promazine
Sulforidazine
Sulpiride
Sultopride
Thioridazine
Thiothixene
Trifluoperazine
Triflupromazine
Trifluperidol
Zuclopenthixol; Atypical antipsychotics: Amisulpride
Asenapine
Blonanserin
Cariprazine
Carpipramine
Clocapramine
Clorotepine
Clozapine
Gevotroline
Iloperidone
Lurasidone
Melperone
Molindone
Mosapramine
Olanzapine
Paliperidone
Perospirone
Piquindone
Quetiapine
Remoxipride
Risperidone
Sertindole
Tiospirone
Zicronapine
Ziprasidone
Zotepine; Antiemetics: AS-8112
Alizapride
Bromopride
Clebopride
Domperidone
Metoclopramide
Thiethylperazine; Others: Amoxapine
Buspirone
Butaclamol
Ecopipam
EEDQ
Eticlopride
Fananserin
Hydroxyzine
L-745,870
Nafadotride
Nuciferine
PNU-99,194
Raclopride
Sarizotan
SB-277,011-A
SCH-23,390
SKF-83,959
Sonepiprazole
Spiperone
Spiroxatrine
Stepholidine
Tetrahydropalmatine
Tiapride
UH-232
Yohimbine

NAMs: SB-269,652

Transporter modulators

DAT	Inhibitors: Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine; Piperidines: 3,4-Dichloropethidine 4-Fluoropethidine 4-Iodopethidine Benocyclidine (BTCP) Desoxypipradrol Dextromethylphenidate Difemetorex Ethylphenidate Methylnaphthidate Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol; Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone; Tropanes: 3-CPMT) 3α-Bis-(4-fluorophenyl)methoxytropane AHN-1055 AHN-2005 Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Iometopane JHW-007 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tenocyclidine Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33; Others: (S)-Duloxetine Adrafinil Armodafinil Amfonelic acid Amineptine Bromantane BTQ BTS-74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Diclofensine Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102677 DOV-21947 DOV-216303 Efavirenz EXP-561 Fencamfamine Fezolamine Fluorenol GYKI-52,895 Indatraline Ketamine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefrine Radafaxine Rimcazole SEP-228431 SEP-228432 Sertraline Sibutramine Tametraline Tedatioxetine Tripelennamine Venlafaxine Enhancers: Luteolin Modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041

VMATs	Inhibitors: Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine NBI-98854 Reserpine Rose bengal SD-809 Tetrabenazine Vanoxerine (GBR-12909)

Releasing agents

Morpholines: Fenbutrazate
Fenmetramide
Morazone
Morforex
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
BOH
Benzphetamine
Buphedrone
Bupropion
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
DMA
DMMA
Dimethylamphetamine
Dimethylcathinone
Ephedrine
Ethcathinone
EBDB
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
4-Hydroxyamphetamine
Iofetamine
Lophophine
Mefenorex
Mephedrone
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methcathinone
Methedrone
MMDA
MMDMA
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Methylone
Morforex
Ortetamine
pBA
pCA
pIA
Pholedrine
Phenethylamine
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Pseudoephedrine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
MDBZP
MeOPP; Others: 2-ADN
2-AI
2-AT
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
IAP
Indanorex
Isometheptene
Methylhexanamine
Naphthylisopropylamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Enzyme inhibitors

PAH	3,4-Dihydroxystyrene

TH	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD	Benserazide Carbidopa DFMD Genistein Methyldopa

MAO	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline Eprobemide Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-deprenyl)

COMT	Entacapone Nitecapone Opicapone Tolcapone

DBH	Disulfiram Dopastin Fusaric acid Nepicastat Tropolone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (levodopa)

Cofactors	Ferrous iron (Fe²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Neurotoxins	Amphetamine DMDHIQ⁺ Methamphetamine MPP⁺ MPTP NMDHIQ⁺ NMNorsal (2-MDTIQ) NMSal Norsalsolinol Oxidopamine (6-OHDA) Rotenone Salsolinol

Others	Activity enhancers: BPAP PPAP; Levodopa prodrugs: XP21279

See also: Adrenergics • Melatonergics • Serotonergics • List of dopaminergic drugs

Serotonergics

5-HT₁ receptor ligands

5-HT_1A	Agonists: 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, nefazodone, trazodone, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine 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 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) U-92016A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 Beta blockers (e.g., alprenolol, cyanopindolol, iodocyanopindolol, oxprenolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_1B	Agonists: CGS-12066A CP-93129 CP-94253 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 Antagonists: AR-A000002 Elzasonan Ergolines (e.g., metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

5-HT_1D	Agonists: 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) 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) Antagonists: Alniditan BRL-15572 Elzasonan Ergolines (e.g., metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone Unknown/unsorted: Ergolines (e.g., lisuride, lysergol, pergolide)

5-HT_1E	Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin (5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine) Antagonists: Metitepine (methiothepin) Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

5-HT_1F	Agonists: BRL-54443 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT) Antagonists: Mianserin Metitepine (methiothepin)

5-HT₂ receptor ligands

5-HT_2A	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., ALD-52, bromocriptine, cabergoline, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Jimscaline MDxx (e.g., MDA, MDMA, MDOH, MMDA) Medifoxamine O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, mCPP, 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 AMDA APD-215 Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, melperone, mosapramine, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Lubazodone LY-393558 Mepiprazole Metitepine (methiothepin) MIN-101 Nantenine Nefazodone Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin S-14671 Sarpogrelate Setoperone Spiperone Spiramide SR-46349B Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Trazodone Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine Unknown/unsorted: Ergolines (e.g., dihydroergotamine, ergometrine (ergonovine), nicergoline)

5-HT_2B	Agonists: 4-Methylaminorex Aminorex Amphetamines (eg., 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) MDxx (e.g., MDA, MDMA, MDOH, MMDA) Piperazines (e.g., mCPP) 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 Asenapine Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) Ketanserin LY-393558 Metadoxine Metitepine (methiothepin) Pirenperone 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) Yohimbine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_2C	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) Lorcaserin MDxx (e.g., MDA, MDMA, MDOH, MMDA) Medifoxamine 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 Dotarizine Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine 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) Trazodone Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

5-HT₃	Agonists: Alcohols (e.g., butanol, ethanol, 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 AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron ICS-205930 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 Unknown/unsorted: LY-53857 Piperazines (e.g., naphthylpiperazine)

5-HT₄	Agonists: 5-MT BIMU8 Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) SL65.0155 Tegaserod Velusetrag Zacopride Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A	Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) Valerenic Acid Antagonists: Asenapine Latrepirdine Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine)

5-HT₆	Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) 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, 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 Latrepirdine Metitepine (methiothepin) MS-245 PRX-07034 Ritanserin Ro04-6790 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) Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine)

5-HT₇	Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT) Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, 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) 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 Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine)

Reuptake inhibitors

SERT	Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Omiloxetine Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine BTS-54505 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN-5652 Milnacipran N-Methyl-PPPA PPPA SEP-227162 Sibutramine Venlafaxine WY-45233 Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): (S)-Duloxetine Brasofensine Dasotraline Desmethylsertraline Diclofensine DOV-102677 DOV-21947 DOV-216303 Liafensine NS-2359 Perafensine SEP-228431 SEP-228432 Tedatioxetine Tesofensine Tricyclic antidepressants (TCAs): Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Trimipramine Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Arylcyclohexylamines (e.g., ketamine, phencyclidine) CP-39332 Cyclobenzaprine Dextromethorphan Dextrorphan Efavirenz Etoperidone EXP-561 Fezolamine LY-393558 Litoxetine Loxapine Lubazodone Mesembrine Mifepristone MIN-117 N-Me-5-HT Nefazodone Nefopam Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine)) PIM-35 Pridefine Roxindole SB-649915 Tofenacin Trazodone Tropanes (e.g., cocaine) Vilazodone Vortioxetine Ziprasidone

VMATs	Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine NBI-98854 Reserpine Rose bengal SD-809 Tetrabenazine Vanoxerine (GBR-12909)

Releasing agents

Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
TAI

Aminotetralins: 6-CAT
8-OH-DPAT
MDAT
MDMAT

Piperazines: 2C-B-BZP
3-MeOPP
BZP
DCPP
MBZP
mCPP
MDBZP
MeOPP
Mepiprazole
pCPP
pFPP
pTFMPP
TFMPP

Tryptamines: 4-Methyl-αET
4-Methyl-αMT
5-CT
5-MeO-αET
5-MeO-αMT
5-MT
αET
αMT
DMT
Tryptamine

Enzyme inhibitors

TPH	AGN-2979 Fenclonine (PCPA)

AAAD	Benserazide Carbidopa Genistein Methyldopa

MAO	Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima

Others

Precursors	L-Tryptophan → 5-HTP

Cofactors	Ferrous iron (Fe²⁺) Magnesium (Mg²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic Acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Neurotoxins	3-CA 4-CAB 5,7-DHT α-Me-DA (3,4-DHA) αET αMT DCA MDA MDMA PBA PCA PIA

Others	Activity enhancers: BPAP PPAP

See also	Serotonin syndrome

See also: Adrenergics • Dopaminergics • Melatonergics

Piperazines

Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES

Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635

Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Piberaline Piribedil Trimetazidine Vesnarinone

Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine Oxatomide SNC-80 Vanoxerine

Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone

Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine Pyridinylpiperazine

Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone

Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol

Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 Zipeprol