Ciclindole

Ciclindole
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine;
CAS Number	32211-97-5;
PubChem CID	36082;
ChemSpider	33189;
UNII	CXJ7G6BYD7;
KEGG	D03619;
ChEMBL	CHEMBL2104160;
Chemical and physical data
Formula	C14H18N2
Molar mass	214.31 g/mol
3D model (Jmol)	Interactive image;
	SMILES c21c(cccc1)nc3c2CC(N(C)C)CC3 ;

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]

Synthesis[edit]

Cyclindole synthesis: Aram Mooradian; Sterling Drug Inc. U.S. Patent 3,959,309

References[edit]

^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
^ ^a ^b Wood PL, McQuade PS (1984). "Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics". Progress in Neuro-psychopharmacology & Biological Psychiatry. 8 (4-6): 773–7. doi:10.1016/0278-5846(84)90057-5. PMID 6152347.

[isbn0-412-46630-9-1] David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.

[pmid6152347-2] Wood PL, McQuade PS (1984). "Ciclindole and flucindole: novel tetrahydrocarbazolamine neuroleptics". Progress in Neuro-psychopharmacology & Biological Psychiatry. 8 (4-6): 773–7. doi:10.1016/0278-5846(84)90057-5. PMID 6152347.

[1]

[2]

v t e Antipsychotics (neuroleptics) (N05A)

Typical	Benzamides Levosulpiride Sulpiride Veralipride^‡ Butyrophenones Azaperone Benperidol Bromperidol Droperidol Fluanisone Haloperidol^# Lenperone Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines Clopimozide Fluspirilene Penfluridol Pimozide Phenothiazines Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine) Chloracizine Chlorproethazine Chlorpromazine Cyamemazine Dixyrazine Fluacizine Fluphenazine Levomepromazine/Methotrimeprazine Mesoridazine Perazine Periciazine Perphenazine Perphenazine 4-aminobutyrate Piperacetazine Pipotiazine Prochlorperazine Promazine Promethazine Sulforidazine Thiethylperazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes Chlorprothixene Clopenthixol Clothixamide Flupentixol Fluprothixene Piflutixol Teflutixol Thiothixene Zuclopenthixol Tricyclics Fluotracen Loxapine Trimipramine Others Butaclamol Prothipendyl

Atypical	Benzamides Amisulpride Nemonapride Remoxipride^‡ Sultopride Tiapride 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 Aripiprazole lauroxil Bifeprunox^§ Brexpiprazole Cariprazine Tricyclics Amoxapine Asenapine Carpipramine Clocapramine Clorotepine Clotiapine Clozapine^# Flumezapine Fluperlapine Gevotroline Metitepine Mosapramine Olanzapine Quetiapine Tenilapine Zotepine Others Blonanserin Lumateperone^† Molindone Pimavanserin RP5063^† Sertindole Zicronapine^§

Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine

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

v t e Tricyclics

Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene

Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine Dibenzepin Dimetacrine Dosulepin/Dothiepin Doxepin Enprazepine Esmirtazapine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Monometacrine Naranol Nitroxazepine Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Azatadine Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium

Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol

Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline Rispenzepine

Others	Adosopine Aminopromazine Atiprosin Beloxepin Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

Ciclindole

Synthesis[edit]

See also[edit]

References[edit]

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine
CAS Number	32211-97-5
PubChem CID	36082
ChemSpider	33189
UNII	CXJ7G6BYD7
KEGG	D03619
ChEMBL	CHEMBL2104160
Chemical and physical data
Formula	C₁₄H₁₈N₂
Molar mass	214.31 g/mol
3D model (Jmol)	Interactive image
SMILES c21c(cccc1)nc3c2CC(N(C)C)CC3