Ciclindole

From Self-sufficiency

Ciclindole
Systematic (IUPAC) name
File:Ciclindole.png
N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine
Clinical data
Routes of administration	Oral
Legal status
Legal status	Uncontrolled
Identifiers
CAS Number	32211-97-5
ATC code	none
PubChem	CID 36082
ChemSpider	33189
Chemical data
Formula	C₁₄H₁₈N₂
Molar mass	214.31 g/mol[[Script error: No such module "String".]]
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Ciclindole (INN; WIN-27,147-2), also known as cyclindole (USAN), is an antipsychotic with a tricyclic structure that was never marketed.^[1]^[2] It displaces spiperone binding in vitro and elevates dopamine levels in the striatum, indicating it acts as a D₂ receptor antagonist.^[2]

References

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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: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl

Atypical

Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone; Benzo(iso)oxazole piperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone; Benzo(iso)thiazole piperazines: Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole • Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Carpipramine • Clocapramine • Clotiapine • Clozapine • Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC • Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin • Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide

Others

Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine • Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin

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^‡Withdrawn from market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

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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 • Lisuride • LSD • Pergolide; Dihydrexidine derivatives: 2-OH-NPA • A-86,929 • Ciladopa • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine; Others: A-68,930 • A-77,636 • A-412,997 • ABT-670 • ABT-724 • Aplindore • Apomorphine • Aripiprazole • Bifeprunox • BP-897 • 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 • 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 • Carpipramine • Clocapramine • Clozapine • Gevotroline • Iloperidone • Lurasidone • Melperone • Molindone • Mosapramine • Ocaperidone • Olanzapine • Paliperidone • Perospirone • Piquindone • Quetiapine • Remoxipride • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Antiemetics: AS-8112 • Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Buspirone • Butaclamol • Ecopipam • EEDQ • Eticlopride • Fananserin • L-745,870 • Nafadotride • Nuciferine • PNU-99,194 • Raclopride • Sarizotan • SB-277,011-A • SCH-23,390 • SKF-83,566 • SKF-83,959 • Sonepiprazole • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine

Reuptake inhibitors

Plasmalemmal

DAT inhibitors

Piperazines: DBL-583 • GBR-12,935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Difemetorex • Ethylphenidate • Methylnaphthidate • Methylphenidate • Phencyclidine • Pipradrol; Pyrrolidines: Diphenylprolinol • Methylenedioxypyrovalerone (MDPV) • Naphyrone • Prolintane • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (¹²³I) • Iometopane • 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: Adrafinil • Armodafinil • Amfonelic acid • Amineptine • Benzatropine (Benztropine) • Bromantane • BTQ • BTS-74,398 • Bupropion (Amfebutamone) • Ciclazindol • Diclofensine • Dimethocaine • Diphenylpyraline • Dizocilpine • DOV-102,677 • DOV-21,947 • DOV-216,303 • Etybenzatropine (Ethylbenztropine) • EXP-561 • Fencamine • Fencamfamine • Fezolamine • GYKI-52,895 • Indatraline • Ketamine • Lefetamine • Levophacetoperane • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Modafinil • Nefopam • Nomifensine • NS-2359 • O-2172 • Pridefrine • Propylamphetamine • Radafaxine • SEP-225,289 • SEP-227,162 • Sibutramine • Tametraline • Tripelennamine

Vesicular

VMAT inhibitors	Deserpidine • Ibogaine • Reserpine • Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-CAB • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amfecloral • Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Famprofazone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA, tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA, homarylamine) • Methylenedioxyphenethylamine (MDPEA, homopiperonylamine) • Methylone • Ortetamine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paredrine (Norpholedrine, Oxamphetamine) • Phenethylamine (PEA) • Pholedrine • Phenpromethamine • Prenylamine • Propylamphetamine • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP, paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP, piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 4-Benzylpiperidine (4-BP) • 5-IAI • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanylaminopropane (IAP) • Indanorex • Isometheptene • Methylhexanamine • Naphthylaminopropane (NAP) • Octodrine • Phthalimidopropiophenone • Propylhexedrine (Levopropylhexedrine) • Tuaminoheptane (Tuamine)

Enzyme inhibitors

Anabolism

PAH inhibitors	3,4-Dihydroxystyrene
TH inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone
AAAD / DDC inhibitors	Benserazide • Carbidopa • Genistein • Methyldopa

Catabolism

MAO inhibitors	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 • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone • Tyrima; MAO-B selective: D-Deprenyl • L-Deprenyl (Selegiline) • Ladostigil • Lazabemide • Milacemide • Mofegiline • Pargyline • Rasagiline
COMT inhibitors	Entacapone • Tolcapone
DBH inhibitors	Bupicomide • Disulfiram • Dopastin • Fusaric acid • Nepicastat • Phenopicolinic acid • 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⁺)
Others	Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Toxins: Oxidopamine (6-Hydroxydopamine)

v t e Tricyclics
Classes	Acridine • Anthracene • Dibenzazepine • Dibenzocycloheptene • Dibenzodiazepine • Dibenzothiazepine • Dibenzothiepin • Dibenzoxazepine • Dibenzoxepin • Phenothiazine • Pyridazinobenzoxazine • Pyridinobenzodiazepine • Thioxanthene
Antidepressants	7-OH-Amoxapine • Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine • Aptazapine • Azepindole • Azipramine • Butriptyline • Cianopramine • Ciclazindol • Ciclopramine • Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine • Dibenzepine • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Esmirtazapine • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Loxapine • Maprotiline • Mariptiline • Mazindol • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Pipofezine • Pirandamine • Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tandamine • Tampramine • Tianeptine • Tienopramine • Trimipramine
Antihistamines	Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine • Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen • Latrepirdine • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene • Promethazine • Propiomazine • Rupatadine • Thiazinamium
Antipsychotics	Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine • Carpipramine • Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine • Clomacran • Clotiapine • Clozapine • Flucindole • Fluotracen • Flupentixol • Fluphenazine • Gevotroline • Homopipramol • Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Metoxepin • Mosapramine • Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Piperacetazine • Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol
Others	Atiprosin • Carbamazepine • Carvedilol • Cyclobenzaprine • Licarbazepine • Methylene Blue • Monatepil • Oxcarbazepine • Oxitriptyline • Pirenzepine • Pirolate • Pitrazepin • Pizotifen • Profenamine

↑ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
↑ ^2.0 ^2.1 Wood PL, McQuade PS (1984). "Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics". Progress in Neuro-psychopharmacology & Biological Psychiatry. 8 (4-6): 773–7. PMID 6152347.

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