CHEBI:4470 - dextromethorphan

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ChEBI Name dextromethorphan
Definition An organic heterotetracyclic compound that is morphinan substituted by a methoxy group at position 3 and a methyl group at position 7. It is used as an antitussive drug for suppressing cough.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H25NO
Net Charge 0
Average Mass 271.39724
Monoisotopic Mass 271.19361
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+/m0/s1
SMILES [H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2Cc2ccc(OC)cc12
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
A poison that interferes with the functions of the nervous system.
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
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ChEBI Ontology
Outgoing dextromethorphan (CHEBI:4470) has role antitussive (CHEBI:51177)
dextromethorphan (CHEBI:4470) has role environmental contaminant (CHEBI:78298)
dextromethorphan (CHEBI:4470) has role neurotoxin (CHEBI:50910)
dextromethorphan (CHEBI:4470) has role NMDA receptor antagonist (CHEBI:60643)
dextromethorphan (CHEBI:4470) has role xenobiotic (CHEBI:35703)
dextromethorphan (CHEBI:4470) is a aromatic ether (CHEBI:35618)
dextromethorphan (CHEBI:4470) is a morphinane alkaloid (CHEBI:25418)
dextromethorphan (CHEBI:4470) is a morphinane-like compound (CHEBI:83818)
dextromethorphan (CHEBI:4470) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming dextromethorphan hydrobromide (CHEBI:4471) has part dextromethorphan (CHEBI:4470)
Synonyms Sources
d-Methorphan ChemIDplus
delta-Methorphan ChemIDplus
Dextromethorphan KEGG COMPOUND
Manual Xrefs Databases
DB00514 DrugBank
Dextromethorphan Wikipedia
HMDB0001920 HMDB
View more database links
Registry Numbers Types Sources
125-71-3 CAS Registry Number ChemIDplus
125-71-3 CAS Registry Number NIST Chemistry WebBook
88549 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17461892 PubMed citation Europe PMC
18198471 PubMed citation Europe PMC
24269965 PubMed citation Europe PMC
Last Modified
25 May 2018