DEXTROMETHORPHAN HYDROBROMIDE Chemical Properties

Melting point:

125-127℃

alpha 

D20 +27.6° (c = 1.5 in water)

pka

pKa 8.83(50% aq EtOH) (Uncertain)

form 

Solid

Water Solubility 

Soluble in water (40 mM), and alcohol (1:10).

EPA Substance Registry System

Morphinan, 3-methoxy-17-methyl-, hydrobromide (1:1),(9.alpha.,13.alpha.,14.alpha.)- (125-69-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

cat,LD50,intravenous,19800ug/kg (19.8mg/kg),LUNGS, THORAX, OR RESPIRATION: DYSPNEASENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE,Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1207, 1972.

DEXTROMETHORPHAN HYDROBROMIDE Usage And Synthesis

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.

Uses

relieving cough

Uses

Cough and cold preparations, Antitussives, OTC cough medicine

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).

brand name

Benylin DM (Parke-Davis); Dextromethorphan Hydrobromide OROS Tablets (Ciba-Geigy); Drixoral Cough (Schering-Plough HealthCare); PediaCare 1 (McNeil Consumer); Romilar (Hoffmann-LaRoche-International); St. Joseph Cough Syrup (Schering-Plough HealthCare).

Therapeutic Function

Antitussive

DEXTROMETHORPHAN HYDROBROMIDE(125-69-9)Related Product Information

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