doxepin   

GtoPdb Ligand ID: 1225

Synonyms: Deptran® | P-3693A | Sinequan®
doxepin is an approved drug (FDA (1969))
Compound class: Synthetic organic
Comment: Doxepin inhibits the sodium-dependent noradrenaline transporter SLC6A2.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 12.47
Molecular weight 279.16
XLogP 3.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN(CCC=C1c2ccccc2OCc2c1cccc2)C
Isomeric SMILES CN(CC/C=C\1/c2ccccc2OCc2c1cccc2)C
InChI InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+
InChI Key ODQWQRRAPPTVAG-GZTJUZNOSA-N
References
1. Auerbach SS, DrugMatrix® and ToxFX® Coordinator National Toxicology Program. 
National Toxicology Program: Dept of Health and Human Services.
Accessed on 02/05/2014. Modified on 02/05/2014. DrugMatrix, https://ntp.niehs.nih.gov/drugmatrix/index.html
2. Booth RG, Moniri NH, Bakker RA, Choksi NY, Nix WB, Timmerman H, Leurs R. (2002)
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.
J. Pharmacol. Exp. Ther., 302 (1): 328-36. [PMID:12065734]
3. Kubo N, Shirakawa O, Kuno T, Tanaka C. (1987)
Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay.
Jpn. J. Pharmacol., 43 (3): 277-82. [PMID:2884340]
4. Tatsumi M, Groshan K, Blakely RD, Richelson E. (1997)
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
Eur. J. Pharmacol., 340 (2-3): 249-58. [PMID:9537821]