CHEBI:4470 - dextromethorphan

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ChEBI Name dextromethorphan
ChEBI ID CHEBI:4470
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
Supplier Information ZINC000003201907
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Dextromethorphan, sold under the brand name Robitussin among others, is a cough suppressant used in many cough and cold medicines. In 2022, the US Food and Drug Administration (FDA) approved the combination dextromethorphan/bupropion to serve as a rapid-acting antidepressant in people with major depressive disorder. It is in the morphinan class of medications with sedative, dissociative, and stimulant properties (at lower doses). Dextromethorphan does not have a significant affinity for the mu-opioid receptor activity typical of morphinan compounds and exerts its therapeutic effects through several other receptors. In its pure form, dextromethorphan occurs as a white powder. When exceeding approved dosages, dextromethorphan acts as a dissociative hallucinogen. It has multiple mechanisms of action, including actions as a nonselective serotonin reuptake inhibitor and a sigma-1 receptor agonist. Dextromethorphan and its major metabolite, dextrorphan, also block the NMDA receptor at high doses, which produces effects similar to other dissociative anesthetics such as ketamine, nitrous oxide, and phencyclidine. It was patented in 1949 and approved for medical use in 1953. In 2022, the combination with promethazine was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions. In 2022, the combination with brompheniramine and pseudoephedrine was the 265th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
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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
InChIKey MKXZASYAUGDDCJ-NJAFHUGGSA-N
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.
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.
metabolite
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.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
oneirogen
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)
IUPAC Names
(4aS,10S,10aS)-6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene
3-methoxy-17-methyl-9α,13α,14α-morphinan
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
C06947 KEGG COMPOUND
D03742 KEGG DRUG
DB00514 DrugBank
Dextromethorphan Wikipedia
HMDB0001920 HMDB
LSM-2726 LINCS
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
Martin E, Narjoz C, Decleves X, Labat L, Lambert C, Loriot MA, Ducheix G, Dualé C, Pereira B, Pickering G (2019)
Dextromethorphan Analgesia in a Human Experimental Model of Hyperalgesia.
Anesthesiology 131, 356-368 [PubMed:31094746]
[show Abstract]
Zarrindast MR, Ownegh V, Rezayof A, Ownegh F (2014)
The involvement of dorsal hippocampus in dextromethorphan-induced state-dependent learning in mice.
Pharmacology, biochemistry, and behavior 116, 90-95 [PubMed:24269965]
[show Abstract]
Shin EJ, Lee PH, Kim HJ, Nabeshima T, Kim HC (2008)
Neuropsychotoxicity of abused drugs: potential of dextromethorphan and novel neuroprotective analogs of dextromethorphan with improved safety profiles in terms of abuse and neuroprotective effects.
Journal of pharmacological sciences 106, 22-27 [PubMed:18198471]
[show Abstract]
Aardema MJ, Robison SH, Gatehouse D, Johnston G (2008)
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.
Regulatory toxicology and pharmacology : RTP 50, 285-293 [PubMed:18160193]
[show Abstract]
Siu A, Drachtman R (2007)
Dextromethorphan: a review of N-methyl-d-aspartate receptor antagonist in the management of pain.
CNS drug reviews 13, 96-106 [PubMed:17461892]
[show Abstract]
Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL (2007)
Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain.
Neurotoxicology 28, 813-818 [PubMed:17573115]
[show Abstract]
Thisted RA, Klaff L, Schwartz SL, Wymer JP, Culligan NW, Gerard G, Pope LE, Berg JE (2006)
Dextromethorphan and quinidine in adult patients with uncontrolled painful diabetic peripheral neuropathy: a 29-day, multicenter, open-label, dose-escalation study.
Clinical therapeutics 28, 1607-1618 [PubMed:17157116]
[show Abstract]
Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA, AVP-923 ALS Study Group (2004)
Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial.
Neurology 63, 1364-1370 [PubMed:15505150]
[show Abstract]
Zhu H, Jenab S, Jones KL, Inturrisi CE (2003)
The clinically available NMDA receptor antagonist dextromethorphan attenuates acute morphine withdrawal in the neonatal rat.
Brain research. Developmental brain research 142, 209-213 [PubMed:12711372]
[show Abstract]
Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ (2000)
Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors.
The Journal of pharmacology and experimental therapeutics 293, 962-967 [PubMed:10869398]
[show Abstract]
Tang YW, Rys PN, Rutledge BJ, Mitchell PS, Smith TF, Persing DH (1998)
Comparative evaluation of colorimetric microtiter plate systems for detection of herpes simplex virus in cerebrospinal fluid.
Journal of clinical microbiology 36, 2714-2717 [PubMed:9705419]
[show Abstract]
Hargreaves RJ, Hill RG, Iversen LL (1994)
Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology.
Acta neurochirurgica. Supplementum 60, 15-19 [PubMed:7976530]
[show Abstract]
Schmitt B, Netzer R, Fanconi S, Baumann P, Boltshauser E (1994)
Drug refractory epilepsy in brain damage: effect of dextromethorphan on EEG in four patients.
Journal of neurology, neurosurgery, and psychiatry 57, 333-339 [PubMed:8158182]
[show Abstract]
Olney JW, Labruyere J, Price MT (1989)
Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs.
Science (New York, N.Y.) 244, 1360-1362 [PubMed:2660263]
[show Abstract]
Last Modified
06 March 2020