8091. Racemethorphan

Nomenclature

CAS number: 510-53-2
(±)-3-Methoxy-17-methylmorphinan; 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.
C18H25NO; mol wt 271.40.
C 79.66%, H 9.28%, N 5.16%, O 5.90%.

Description and references

Prepn: Schnider, Grüssner, US 2676177 (1954 to Hoffmann-La Roche). Prepn of d-form: eidem, ibid.; H"afliger 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).

Chemical structure

Derivative

Hydrobromide.

Nomenclature

CAS number: 6031-86-3
Ro-1-5470.
C18H25NO.HBr; mol wt 352.31.
C 61.36%, H 7.44%, N 3.98%, O 4.54%, Br 22.68%.

Properties

Crystals, mp 124-126°.

Derivative

d-Form hydrobromide.

Nomenclature

CAS number: 125-69-9
Dextromethorphan hydrobromide; demorphan hydrobromide; Ro-1-5470/5; Benylin (Warner-Lambert); Canfodion (Gentili); Cosylan (Parke-Davis); Hihustan (Maruko).

Description and 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°. [α]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.

Derivative

l-Form hydrobromide.

Nomenclature

CAS number: 125-68-8
Levomethorphan hydrobromide; Ro-1-5470/6; Ro-1-7788.

Properties

Occurs as the dihydrate, crystals, mp 124-126°. [α]D20 -26.3°.

Note

Racemethorphan and levomethorphan are controlled substances (opiates): 21 CFR, 1308.12.

Therapeutic Category

Antitussive.

Keywords

Antitussive

Dextromethorphan: Antitussive