dextromethorphan   

GtoPdb Ligand ID: 6953

Synonyms: d-methorphan
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
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
SMILES / InChI / InChIKey
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
InChI Key MKXZASYAUGDDCJ-NJAFHUGGSA-N
No information available.
Summary of Clinical Use
Used as an antitussive medication.
Mechanism Of Action and Pharmacodynamic Effects
The exact role of σ–receptors is difficult to establish as many σ–agonists also bind to other targets such as the κ-opioid receptor and the NMDA glutamate receptors. Despite being one of the most widely used antitussive agents dextromethorphan's precise mechanism of action has not been fully elucidated. Dextromethorphan displays antagonist activity at the cationic NMDA receptor channel1 and agonist activity at σ receptors. Evidence from animal models suggests that the σ receptor is likely involved in the anttussive activity of this drug [3].