(1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

• ChemBase ID: 396
• Molecular Formular: C18H25NO
• Molecular Mass: 271.3972
• Monoisotopic Mass: 271.19361443
• SMILES: [C@@]123c4c(C[C@@H]([C@H]1CCCC3)N(CC2)C)ccc(c4)OC
• Canonical SMILES: COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)N(CC1)C
• 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

NAMES AND DATABASE IDS

Names

• 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: Antussan; Balminil DM; Balminil DM Children; Benylin Adult Formula Cough Suppressant; Benylin DM; Benylin DM 12 Hour; Benylin DM for Children; Benylin DM for Children 12 Hour; Benylin Pediatric Cough Suppressant; Calmylin #1; Canfodion; Cosylan; Cough-X; Creo-Terpin; Delsym; Delsym Cough Formula; Diabe-Tuss DM Syrup; Dormetan; Dormethan; Hihustan M.; Hold DM; Koffex DM; Medicon; Methorate Hydrobromide; Methorphan; Metrorat; Novahistex DM; Novahistine DM; Pertussin CS Children's Strength; Pertussin DM Extra Strength; Robitussin Maximum Strength Cough Suppressant; Robitussin Pediatric; Robitussin Pediatric Cough Suppressant; Romilar; Sucrets 4 Hour Cough Suppressant; Triaminic DM Long Lasting for Children; Trocal; Tusilan; Tussade; Vicks 44 Cough Relief
• Synonyms: D-Methorphan; D-Methorphan Hydrobromide; Delta-Methorphan; Dextromethorfan [Czech]; Destrometerfano [Dcit]; Demorphan; Demorphan Hydrobromide; Demorphine; Dextromethorphan Bromhydrate; Dextromethorphan Bromide; Dextrometorfano [INN-Spanish]; Dextrometorphan; Dextromorphan; Dexyromethorphan; L-Methorphan; Levomethorphan; Levomethorphan [Ban:Dcf:Inn]; Levomethorphane [INN-French]; Levomethorphanum [INN-Latin]; Levometorfano [INN-Spanish]; Dextromethorphan

Database IDs

• CAS Number: 125-71-3
• PubChem SID: 160963859
• PubChem CID: 5360696

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.050376788
• LogD (pH = 7.4): 1.0825826
• Log P: 3.4937744
• Molar Refractivity: 82.5632 cm^3
• Polarizability: 32.306057 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.75
• LOG S: -4.5
• Solubility (Water): 8.51e-03 g/l

PROPERTIES

Physical Property

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

DETAILS

DrugBank - DB00514

• 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