CHEBI:4470 - dextromethorphan

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ChEBI Name dextromethorphan
ChEBI ID CHEBI:4470
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
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
InChIKey MKXZASYAUGDDCJ-CGTJXYLNSA-N
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.
neurotoxin
A poison that interferes with the functions of the nervous system.
xenobiotic
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.
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-like compound (CHEBI:83818)
dextromethorphan (CHEBI:4470) is a organic heterotetracyclic compound (CHEBI:38163)
IUPAC Name
3-methoxy-17-methylmorphinan
Synonyms Sources
d-Methorphan ChemIDplus
delta-Methorphan ChemIDplus
Dextromethorphan KEGG COMPOUND
DXM ChEBI
Database Links Databases
C06947 KEGG COMPOUND
D03742 KEGG DRUG
DB00514 DrugBank
Dextromethorphan Wikipedia
HMDB01920 HMDB
View more database links
Registry Numbers Types Sources
125-71-3 CAS Registry Number KEGG COMPOUND
125-71-3 CAS Registry Number NIST Chemistry WebBook
125-71-3 CAS Registry Number ChemIDplus
88549 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17461892 PubMed citation CiteXplore
18198471 PubMed citation CiteXplore
24269965 PubMed citation CiteXplore
Last Modified
20 November 2014