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Cyanodothiepin

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Chemical compound
Pharmaceutical compound
Cyanodothiepin
Clinical data
Other namesBTS-56424
ATC code
  • None
Identifiers
  • 11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenzo[b,e]thiepine-2-carbonitrile
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H20N2S
Molar mass 320.45 g·mol−1
3D model (JSmol)
  • CN(C)CC/C=C1C2=C(C=CC(C#N)=C2)SCC3=C/1C=CC=C3
  • 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-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]

See also

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References

[edit ]
  1. ^ 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.
  2. ^ a b Jucker E (2000). Progress in Drug Research. Birkhäuser. pp. 79–80. ISBN 978-3-7643-6113-6 . Retrieved 2011年11月25日.
  3. ^ 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年11月25日.
SSRIs Tooltip Selective serotonin reuptake inhibitors
SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors
NRIs Tooltip Norepinephrine reuptake inhibitors
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants
SARIs Tooltip Serotonin antagonist and reuptake inhibitors
SMS Tooltip Serotonin modulator and stimulators
Others
TCAs Tooltip Tricyclic antidepressants
TeCAs Tooltip Tetracyclic antidepressants
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Non-selective
MAOA Tooltip Monoamine oxidase A-selective
MAOB Tooltip Monoamine oxidase B-selective
Miscellaneous
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
DAT Tooltip Dopamine transporter
(DRIs Tooltip Dopamine reuptake inhibitors)
NET Tooltip Norepinephrine transporter
(NRIs Tooltip Norepinephrine reuptake inhibitors)
SERT Tooltip Serotonin transporter
(SRIs Tooltip Serotonin reuptake inhibitors)
VMATs Tooltip Vesicular monoamine transporters
Others
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
5-HT1
5-HT1A
  • Positive allosteric modulators: Oleamide
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3 –7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • Negative allosteric modulators: Oleamide
Classes
Antidepressants
(Tricyclic antidepressants (TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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