CHEBI:4470 - dextromethorphan

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ChEBI Name dextromethorphan
Definition A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:92579
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Formula C18H25NO
Net Charge 0
Average Mass 271.404
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+/m1/s1
SMILES C=1C=2C[C@H]3[C@@]4([C@](C2C=C(C1)OC)(CCCC4)CCN3C)[H]
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.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
Any substance that produces or enhances dream-like states of consciousness.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dextromethorphan (CHEBI:4470) has functional parent dextrorphan (CHEBI:29133)
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 oneirogen (CHEBI:146270)
dextromethorphan (CHEBI:4470) has role prodrug (CHEBI:50266)
dextromethorphan (CHEBI:4470) has role xenobiotic (CHEBI:35703)
dextromethorphan (CHEBI:4470) is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene (CHEBI:146178)
dextromethorphan (CHEBI:4470) is enantiomer of levomethorphan (CHEBI:146176)
Incoming dextromethorphan hydrobromide (CHEBI:4471) has part dextromethorphan (CHEBI:4470)
racemethorphan (CHEBI:146177) has part dextromethorphan (CHEBI:4470)
levomethorphan (CHEBI:146176) is enantiomer of dextromethorphan (CHEBI:4470)
INNs Sources
dextromethorphan WHO MedNet
dextrométhorphane WHO MedNet
dextromethorphanum WHO MedNet
dextrometorfano WHO MedNet
Synonyms Sources
(+)-3-methoxy-N-methylmorphinan ChemIDplus
(+)-dextromethorphan DrugCentral
(9α,13α,14α)-3-methoxy-17-methylmorphinan ChemIDplus
3-methoxy-17-methyl-9α,13α,14α-morphinan NIST Chemistry WebBook
BA 2666 ChemIDplus
BA-2666 ChEBI
d-Methorphan DrugCentral
D-methorphan NIST Chemistry WebBook
destrometerfano ChemIDplus
dextromethorfan ChemIDplus
DXM ChemIDplus
Brand Names Sources
Albutussin ChemIDplus
Antussan ChEBI
Balminil DM ChEBI
Benylin DM HMDB
Calmylin ChEBI
Delsym NIST Chemistry WebBook
Dextromorphan ChemIDplus
Medicon NIST Chemistry WebBook
Romilar NIST Chemistry WebBook
Tusilan NIST Chemistry WebBook
Manual Xrefs Databases
842 DrugCentral
DB00514 DrugBank
Dextromethorphan Wikipedia
HMDB0001920 HMDB
View more database links
Registry Numbers Types Sources
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
10869398 PubMed citation Europe PMC
12711372 PubMed citation Europe PMC
15505150 PubMed citation Europe PMC
17157116 PubMed citation Europe PMC
17461892 PubMed citation Europe PMC
17573115 PubMed citation Europe PMC
18160193 PubMed citation Europe PMC
18198471 PubMed citation Europe PMC
24269965 PubMed citation Europe PMC
2660263 PubMed citation Europe PMC
31094746 PubMed citation Europe PMC
7976530 PubMed citation Europe PMC
8158182 PubMed citation Europe PMC
9705419 PubMed citation Europe PMC
Last Modified
06 March 2020