racemethorphan

Originator

Symptom 1 ,Parke Davis,US,1977

The Uses of racemethorphan

Racemethorphan is the racemic mixture of Dextromethorphan (D299445) and Levomethorphan (L375850). Dextromethorphan is an antitussive compound showing analgesic properties; used in cough medication formulations. Levomethorphan is an antitussive medicine, a narcotic and controlled substance.

Definition

ChEBI: 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene is an organic heterotetracyclic compound that is 1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene which is substituted by a methoxy group at position 6 and a methyl group at position 11. It is an aromatic ether, a morphinane alkaloid, a morphinane-like compound and an organic heterotetracyclic compound.

Manufacturing Process

The methylation of 51.4 parts by weight of D,L-3-hydroxy-N-methylmorphinan is carried out with a methylating solution obtained from 51.5 parts by weight of phenyl-trimethylammonium-chloride. The D,L-3-methoxy-Nmethyl-morphinan is isolated in the form of its hydrobromide, which melts with 1 mol of water at 92°-94°C,without water at 239°-240°C. The base isolated from the aqueous solution by means of sodium carbonate melts at 81°-83°C.
27.1 parts by weight of D,L-3-methoxy-N-methyl-morphinan base are dissolved with 15.0 parts by weight of D-tartaric acid in 150 parts by volume of hot alcohol. The solution is cooled and seeded with (+)-3-methoxy-Nmethyl-morphinan-tartrate.The (+)-form which is difficultly soluble in alcohol separates, is filtered by suction and washed with a little alcohol.
[The (-)-form may be crystallized from the residue obtained by concentrating the mother liquor, separating therefrom as much as possible of the (+)-form and adding acetone].
The (+)-3-methoxy-N-methyl-morphinan-tartrate melts with 1 mol of water at 195°-196°C [α]D20 =+30.6° (c = 1.5 in water). The (+) base melting at 108°-109°C may be obtained from the tartrate by means of sodium carbonate. The corresponding hydrobromide melts at 122°-124°C [α]D20 =+27.6° (c = 1.5 in water).

Therapeutic Function

Antitussive