Cyanodothiepin

Cyanodothiepin
Clinical data
Other names	BTS-56424
ATC code	None;
Identifiers
	IUPAC name 11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]thiepine-2-carbonitrile;
CAS Number	90667-37-1;
PubChem CID	13276753;
ChemSpider	30780728;
CompTox Dashboard (EPA)	DTXSID20534059 ;
Chemical and physical data
Formula	C20H20N2S
Molar mass	320.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CC/C=C1C2=C(C=CC(C#N)=C2)SCC3=C/1C=CC=C3;
	InChI InChI=1S/C20H20N2S/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-23-20-10-9-15(13-21)12-19(18)20/h3-4,6-10,12H,5,11,14H2,1-2H3/b18-8+; Key:FSIRGTNPQFDCCD-QGMBQPNBSA-N;

Cyanodothiepin (developmental code name BTS-56424) is a tricyclic antidepressant (TCA) acting as a potent and highly selective (over norepinephrine and dopamine uptake) inhibitor of the reuptake of serotonin that was never marketed.^[1]^[2]^[3] It also has moderate affinity for the muscarinic acetylcholine receptors and weak/negligible affinity for the α₁-adrenergic, 5-HT_2A, D₁, and D₂ receptors;^[1]^[2]^[3] the H₁ receptor has not been assayed,^[3] but cyanodothiepin is less sedating than the related drug cianopramine, suggesting that its antihistamine activity is not as pronounced as other TCAs.^[1]^[3] Cyanodothiepin is active in the forced swimming test (FST), implying that it may possess antidepressant properties in humans. However, it is only weakly active compared to cianopramine and imipramine in monoamine depletion-based tests of antidepressant potential.^[1]

References

^ ^a ^b ^c ^d Luscombe GP, Buckett WR (1993). "Pharmacology of Cyanodothiepin (BTS 56 424), a Selective 5-Hydroxytryptamine Reuptake Inhibitor". Drug Development Research. 29 (3): 235–248. doi:10.1002/ddr.430290311. S2CID 84257024.
^ ^a ^b Jucker E (2000). Progress in Drug Research. Birkhäuser. pp. 79–80. ISBN 978-3-7643-6113-6. Retrieved 2011-11-25.
^ ^a ^b ^c ^d Olivier B, van Wijngaarden I, Soudijn W (1997). Serotonin Receptors and their Ligands. Elsevier. p. 332. ISBN 978-0-444-82041-9. Retrieved 2011-11-25.

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[doi10.1002/ddr.430290311-1] Luscombe GP, Buckett WR (1993). "Pharmacology of Cyanodothiepin (BTS 56 424), a Selective 5-Hydroxytryptamine Reuptake Inhibitor". Drug Development Research. 29 (3): 235–248. doi:10.1002/ddr.430290311. S2CID 84257024.

[Jucker2000-2] Jucker E (2000). Progress in Drug Research. Birkhäuser. pp. 79–80. ISBN 978-3-7643-6113-6. Retrieved 2011-11-25.

[OlivierWijngaarden1997-3] Olivier B, van Wijngaarden I, Soudijn W (1997). Serotonin Receptors and their Ligands. Elsevier. p. 332. ISBN 978-0-444-82041-9. Retrieved 2011-11-25.

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[2]

[3]

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Beloxepin Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Perlapine Phenindamine Pimethixene Pirolate 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
Anticholinergics	Darenzepine Dipitramine Nuvenzepine Pirenzepine Profenamine Rispenzepine Siltenzepine Telenzepine Tripitramine Tropatepine Zolenzepine
Others	Adosopine Aminopromazine Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole

Cyanodothiepin

See also

References