(1R,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-triene

• ChemBase ID: 126931
• Molecular Formular: C18H25NO
• Molecular Mass: 271.3972
• Monoisotopic Mass: 271.19361443
• SMILES: O(c1ccc2c(c1)[C@@]13[C@@H]([C@H](N(CC1)C)C2)CCCC3)C
• 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-KBAYOESNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2,4,6-triene
• IUPAC Traditional name: dextromethorphan
• Brand Name: Robitussin, Delsym, DM, DexAlone, Duract
• Synonyms: Dextromethorphan

Database IDs

• CAS Number: 125-71-3
• PubChem SID: 162221257
• PubChem CID: 6916184; 15978238
• ATC CODE: R05DA09
• CHEMBL: 52440
• Chemspider ID: 13109865
• DrugBank ID: DB00514
• KEGG ID: D03742
• Unique Ingredient Identifier: 7355X3ROTS
• Wikipedia Title: Dextromethorphan
• Medline Plus: a682492

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Melting Point: 111°C (231.8°F)

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 11%
• Excretion: Renal
• Half Life: 1.4–3.9 hours
• Metabolism: Hepatic (liver) enzymes: major CYP2D6, minor CYP3A4, and minor CYP3A5
• Legal Status: OTC (US); S2 (Australia)
• Pregnancy Category: A (Australia); C (US)