Dextromethorphan

• Catalog No.: DB00514
• CAS Number: 125-71-3
• M. F.: C18H25NO
• M. W.: 271.3972

SYNONYMS

• IUPAC name: (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
• IUPAC Traditional name: dextromethorphan
• Brand Name: Novahistine DM; Cosylan; Creo-Terpin; Balminil DM; Benylin DM 12 Hour; Delsym; Delsym Cough Formula; Diabe-Tuss DM Syrup; Hihustan M.; Koffex DM; Antussan; Benylin Adult Formula Cough Suppressant; Benylin DM for Children 12 Hour; Benylin Pediatric Cough Suppressant; Calmylin #1; Cough-X; Hold DM; Medicon; Metrorat; Novahistex DM; Pertussin CS Children's Strength; Robitussin Pediatric Cough Suppressant; Romilar; Sucrets 4 Hour Cough Suppressant; Tusilan; Vicks 44 Cough Relief; Balminil DM Children; Benylin DM; Benylin DM for Children; Canfodion; Dormetan; Dormethan; Methorate Hydrobromide; Methorphan; Pertussin DM Extra Strength; Robitussin Maximum Strength Cough Suppressant; Robitussin Pediatric; Triaminic DM Long Lasting for Children; Trocal; Tussade
• Synonyms: Demorphine; Dexyromethorphan; Levometorfano [INN-Spanish]; D-Methorphan; D-Methorphan Hydrobromide; Demorphan; Levomethorphanum [INN-Latin]; Dextromethorfan [Czech]; Dextromethorphan Bromhydrate; Dextromethorphan Bromide; Dextromorphan; L-Methorphan; Levomethorphane [INN-French]; Delta-Methorphan; Destrometerfano [Dcit]; Demorphan Hydrobromide; Dextrometorfano [INN-Spanish]; Dextrometorphan; Levomethorphan; Levomethorphan [Ban:Dcf:Inn]

DATABASE IDS

• CAS Number: 125-71-3

PROPERTIES

• Hydrophobicity(logP): 3.6
• Solubility: 74.7 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: The d-isomer of the codeine analog of levorphanol. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]
• Indication: For treatment and relief of dry cough.
• Pharmacology: Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.
• Absorption: Rapidly absorbed from the gastrointestinal tract.
• Half Life: 3-6 hours
• References: Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. [Pubmed] ; Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. [Pubmed] ; Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. [Pubmed] ; Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. [Pubmed] ; Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. Pubmed
• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. Pubmed
• Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. Pubmed
• Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. Pubmed
• Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. Pubmed