dextromethorphan   Click here for help

GtoPdb Ligand ID: 6953

Synonyms: d-methorphan
Approved drug
dextromethorphan is an approved drug (FDA (no history prior to 1982))
Compound class: Synthetic organic
Comment: Dextromethorphan is a morphinan class sedative. It is available over-the-counter (OTC) for use as an antitussive. At doses much higher than medically recommended, dextromethorphan is used recreationally for its dissociative anesthetic and euphoria producing effects.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 12.47
Molecular weight 271.19
XLogP 3.61
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
Isomeric SMILES COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)N(CC1)C
InChI InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
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2. Ganapathy ME, Prasad PD, Huang W, Seth P, Leibach FH, Ganapathy V. (1999)
Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line.
J Pharmacol Exp Ther, 289 (1): 251-60. [PMID:10087012]
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The antitussive activity of delta-opioid receptor stimulation in guinea pigs.
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