Originator
Symptom 1 ,Parke Davis,US,1977
Uses
It is used as a potentially useful NMDA receptor agonist. it is usually used as central nervous antitussive, cough suppressant. This is one of the most popular ingredients in over-the-counter cold and cough medications. Dextromethorphan hydrobromide may be added to other preparations to help treat pain and a variety of other disturbances as well. It is used as a pharmaceutical raw material.
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).
