Cyanodothiepin

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-HT2A, 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]

Cyanodothiepin
Clinical data
Other namesBTS-56424
ATC code
  • None
Identifiers
IUPAC name
  • 11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]thiepine-2-carbonitrile
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H20N2S
Molar mass320.45 g·mol−1
3D model (JSmol)
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

See also

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