Racemethorphan
Title: Racemethorphan
CAS Registry Number: 510-53-2
CAS Name: (±)-3-Methoxy-17-methylmorphinan
Additional Names: dl-cis-1,3,4,9,10,10a-hexahydro-6-methoxy-11-methyl-2H-10,4a-iminoethanophenanthrene; dl-cis-1,2,3,9,10,10a-hexahydro-6-methoxy-11-methyl-4H-10,4a-iminoethanophenanthrene; deoxydihydrothebacodine; methorphan
Molecular Formula: C18H25NO
Molecular Weight: 271.40
Percent Composition: C 79.66%, H 9.28%, N 5.16%, O 5.90%
Literature References: Prepn: Schnider, Grüssner, US 2676177 (1954 to Hoffmann-La Roche). Prepn of d-form: eidem, ibid.; Häfliger et al., Helv. Chim. Acta 39, 2053 (1956). Prepn of l-form hydrobromide: Corrodi et al., ibid. 42, 215 (1959). Crystal structure and absolute configuration of d-form hydrobromide: L. Gylbert, D. Carlstrom, Acta Crystallogr. B, 2833 (1977).
 
Derivative Type: Hydrobromide
CAS Registry Number: 6031-86-3
Manufacturers' Codes: Ro-1-5470
Molecular Formula: C18H25NO.HBr
Molecular Weight: 352.31
Percent Composition: C 61.36%, H 7.44%, N 3.98%, O 4.54%, Br 22.68%
Properties: Crystals, mp 124-126°.
Melting point: mp 124-126°
 
Derivative Type: d-Form hydrobromide
CAS Registry Number: 125-69-9
Additional Names: Dextromethorphan hydrobromide; demorphan hydrobromide
Manufacturers' Codes: Ro-1-5470/5
Trademarks: Benylin (Warner-Lambert); Canfodion (Gentili); Cosylan (Parke-Davis); Hihustan (Maruko)
Literature References: HPLC-MS/MS determn of free base in urine: M. L. Constanzer et al., J. Chromatogr. B 816, 297 (2005).
Properties: Occurs as the monohydrate, crystals, mp 122-124°. [a]D20 +27.6° (c = 1.5 in water). Approx soly in water: 1.5% at 25°, 5% at 50°, 25% at 85°. Soly (w/w): 25% in 95% ethanol at room temp, 10% in glycerol. Sol in propylene glycol, chloroform. Practically insol in ether. pH of a 1% aq soln: 5.2-6.5. Long range stability of aq solns obtained by adjusting pH within 4-5.6. Reacts with alkalies forming the free base which is practically insol in water.
Melting point: mp 122-124°
Optical Rotation: [a]D20 +27.6° (c = 1.5 in water)
 
Derivative Type: l-Form hydrobromide
CAS Registry Number: 125-68-8
Additional Names: Levomethorphan hydrobromide
Manufacturers' Codes: Ro-1-5470/6; Ro-1-7788
Properties: Occurs as the dihydrate, crystals, mp 124-126°. [a]D20 -26.3°.
Melting point: mp 124-126°
Optical Rotation: [a]D20 -26.3°
 
NOTE: Racemethorphan and levomethorphan are controlled substances (opiates): 21 CFR, 1308.12.
Therap-Cat: Antitussive.
Keywords: Antitussive.

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