DEXTROMETHORPHAN HYDROBROMIDE Chemical Properties
- Melting point:125-127℃
- alpha D20 +27.6° (c = 1.5 in water)
- pkapKa 8.83(50% aq EtOH) (Uncertain)
- Water Solubility Soluble in water (40 mM), and alcohol (1:10).
- EPA Substance Registry SystemMorphinan, 3-methoxy-17-methyl-, hydrobromide (1:1),(9.alpha.,13.alpha.,14.alpha.)- (125-69-9)
DEXTROMETHORPHAN HYDROBROMIDE Usage And Synthesis
- OriginatorSymptom 1 ,Parke Davis,US,1977
- Usesrelieving cough
- UsesCough and cold preparations, Antitussives, OTC cough medicine
- Manufacturing ProcessThe 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
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 nameBenylin 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 FunctionAntitussive
- Hydrogen bromide Racemethorphan hydrobromide Dextromethorphan Hydrobromide powder DEXTROMETHORPHAN HYDROBROMIDE MONOHYDRATE IMP.A (EP): ENT-3-METHOXYMORPHINAN HYDROCHLORIDE DEXTROMETHORPHAN HYDROBROMIDE MONOHYDRATE IMP. B (EP) AS (L)-TARTRATE: ENT-17-METHYLMORPHINAN-3-OL (L)-TARTRATE DEXTROMETHORPHAN HYDROBROMIDE MONOHYDRATE IMP. C (EP): ENT-3-METHOXY-17-METHYLMORPHINAN-10-ONE Dextromethorphan Hydrobromide, substrate for Cyt P450 2D6 2-ETHYLHEXYLAMINE HYDROBROMIDE racemorphan Racemethorphan [as d-form] DEXTROMETHORPHAN HYDROBROMIDE DEXTRORPHAN D-TARTRATE (R)-2-AMINOTETRALIN (R)-(+)-6-METHOXY 2-AMINOTETRALIN DEXTROMETHORPHAN-D3 HBR MONHYDRATE Dextromethorphan hydrobromide monohydrate