(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene hydrobromide

• ChemBase ID: 119830
• Molecular Formular: C18H26BrNO
• Molecular Mass: 352.30914
• Monoisotopic Mass: 351.11977646
• SMILES: [C@]123c4c(C[C@H]([C@@H]1CCCC3)N(CC2)C)ccc(c4)OC.Br
• Canonical SMILES: COc1ccc2c(c1)[C@]13CCCC[C@H]3[C@@H](C2)N(CC1)C.Br
• InChI: InChI=1S/C18H25NO.BrH/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;1H/t15-,17+,18+;/m0./s1
• InChIKey: MISZALMBODQYFT-FLCXFYETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene hydrobromide
• IUPAC Traditional name: levomethorphan hydrobromide; (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene hydrobromide
• Synonyms: (4bR,8aR,9R)-3-methoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene hydrobromide; DXM; DM; Dextromethorphan Hydrobromide

Database IDs

• CAS Number: 510-53-2
• PubChem SID: 162108182
• PubChem CID: 5486607

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

Pharmacology Properties

• Mechanism of Action: NMDA receptor antagonist

Product Information

• Salt Data: HBr
• Application(s): Anticonvulsant and neuroprotective props.; Antitussive

REFERENCES

• Schnider, O. et al., Helv. Chim. Acta, 1950, 33, 1437; 1951, 34, 2211, (synth, resoln)
• Hfliger, D. et al., Helv. Chim. Acta, 1959, 39, 2053, (deriv)
• Corrodi, H. et al., Helv. Chim. Acta, 1959, 42, 212, (abs config)
• Yoshihiro, T. et al., Tet. Lett., 1975, 2853, (cmr)
• Gylbert, L. et al., Acta Cryst. B, 1977, 33, 2833, (deriv)
• Wainer, I.W. et al., J.O.C., 1982, 47, 1761, (deriv, resoln)
• Meyers, A.I. et al., J.O.C., 1986, 51, 872, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4961, (synonyms)
• Tortella, F.C. et al., Trends Pharmacol. Sci., 1989, 10, 501, (pharmacol, rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 746
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DBE150; DBE200; DBE800; DYF000; LFG000; MKR250; MLZ000