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DEXTROMETHORPHAN HYDROBROMIDE

Basic information Safety Related Supplier
DEXTROMETHORPHAN HYDROBROMIDE Basic information
DEXTROMETHORPHAN HYDROBROMIDE Chemical Properties
Safety Information
  • Hazard Codes Xn
  • Risk Statements 22
  • Safety Statements 36/37
  • RIDADR 3249
  • HazardClass 6.1(b)
  • PackingGroup III
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 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 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
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