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DEXTROMETHORPHAN Basic information
DEXTROMETHORPHAN Chemical Properties
Safety Information
  • Hazard Codes F,T
  • Risk Statements 11-23/24/25-39/23/24/25
  • Safety Statements 16-36/37-45
  • RIDADR 3249
  • WGK Germany 1
  • RTECS QD0194000
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 2933492250
  • ToxicityLD50 oral in rat: 116mg/kg
  • UsesAntitussive.
  • DefinitionChEBI: An organic heterotetracyclic compound that is morphinan substituted by a methoxy group at position 3 and a methyl group at position 7. It is used as an antitussive drug for suppressing cough.
  • IndicationsThis drug possesses a pronounced anticough effect and minimal action on the CNS. It is not addictive.
  • 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);Agrippol;Dextophan;Dextrophen.
  • Biological FunctionsDextromethorphan hydrobromide is the D-isomer of levorphanol. It lacks CNS activity but acts at the cough center in the medulla to produce an antitussive effect. It is half as potent as codeine as an antitussive. Anecdotal reports of abuse exist, but studies of abuse potential are lacking. It has few side effects but does potentiate the activity of monoamine oxidase inhibitors, leading to hypotension and infrequently coma. Dextromethorphan is often combined in lozenges with the local anesthetic benzocaine, which blocks pain from throat irritation due to coughing.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 30, p. 1769, 1965 DOI: 10.1021/jo01017a014
  • General DescriptionDextromethorphan is the dextrorotatory form of levorphanolwith a methoxy group on the 3-position. It is availablein more than 140 over-the-counter (OTC) cough and coldformulations. Evidence-based reviews have been unable toconclude that it is more effective than placebo in reducingcough. Like (+) and (-) levorphanol, (+) dextromethorphanis a potent NMDA antagonist and, in higher than recommendeddoses, has the potential for causing dissociativeanesthetic effects similar to ketamine or phencyclidine (PCP).The OTC status and availability of pure dextromethorphanpowder online has contributed greatly to its abuse in recentyears. DAWN reports that in 2004, there were approximately12,500 emergency room visits involving dextromethorphanwith 44% of those involving abuse of the drug. The 2006National Survey on Drug Abuse report shows that nearly 1million persons aged 12 to 25 years (1.7%) misused OTCcough and cold medications in the past year.
    Dextromethorphan’s ability to antagonize the NMDA receptorhas led to its use to treat phantom pain, diabetic neuropathy,and postoperative acute pain.
  • Chemical SynthesisDextromethorphan, (9α,13α,14α)-3-methoxy-17-methylmorphinane (23.2.1), is synthesized from ()-3-hydroxy-N-methylmorphinane by methylating the phenol hydroxyl group using phenyltrimethylammonium chloride and sodium methoxide in methanol. The resulting racemic product ()-3-methoxy-N-methylmorphinane is separated into isomers using D-tartaric acid, which produces dextromethor-phan.

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