From Learn Chemistry Wiki
- Main ChemSpider page
- Molecular formula: C18H25NO
- Molar mass: 271.397
- CAS Registry Number: Not available
- Appearance: Not available
- Melting point: Not available
- Boiling point: Not available
- Solubility: Not available
- Safety sheet: Not available
- Spectra: Massbank MS (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38), also check on SDBS. Add Spectra (Help).
Dextromethorphan (DXM or DM) is a drug of the morphinan class with sedative, dissociative, and stimulant properties (at higher doses). It is a cough suppressant in many over-the-counter cold and cough medicines including generic labels and store brands, Benylin DM, Mucinex DM, Camydex-20 tablets, Robitussin, NyQuil, Dimetapp, Vicks, Coricidin, Delsym, TheraFlu, Cheracol D, and others. Dextromethorphan has also found numerous other uses in medicine, ranging from pain relief (as either the primary analgesic, or an opioid potentiator) over psychological applications to the treatment of addiction. It is sold in syrup, tablet, spray, and lozenge forms. In its pure form, dextromethorphan occurs as a white powder.
DXM is also used recreationally. When exceeding approved dosages, dextromethorphan acts as a dissociative anesthetic. Its mechanism of action is via multiple effects, including actions as a nonselective serotonin reuptake inhibitor and a sigma-1 receptor agonist. DXM and its major metabolite, dextrorphan, also act as an NMDA receptor antagonist at high doses, which produces effects similar to, yet distinct from, the dissociative states created by other dissociative anesthetics such as ketamine and phencyclidine.
The metabolic pathway continues from dextrophan to 3-methoxymorphinan to 3-hydroxymorphinan. The 3-methoxymorphinan metabolite produces local anesthetic effects in rats, with potency between dextrophan and DMX, while 3-hydroxymorphinan has potent neuroprotective and neurotrophic effects.
(14alpha)-3-Methoxy-17-methylmorphinan (IUPAC Name); (9a,13a,14a)-3-Methoxy-17-methylmorphinan; (9alpha,13alpha,14alpha)-17-methyl-3-(methyloxy)morphinan; (9alpha,13alpha,14alpha)-3-Methoxy-17-methylmorphinan; 3-Methoxy-17-methyl-9a,13a,14a-morphinan; Balminil DM; Benylin Pediatric Cough Suppressant; Cough-X; Creo-Terpin; Delsym Cough Formula; Demorphine; Dextrometorphan; Dexyromethorphan; Diabe-Tuss DM Syrup; Dormetan; Hold DM; Koffex DM; (9Alpha,13alpha,14alpha)-3-methoxy-17-methyl-morphinan; (9-Alpha,13-alpha,14-alpha)-3-methoxy-17-methyl-morphinan; Novahistex DM; Novahistine DM; Pertussin CS Children's Strength; Pertussin DM Extra Strength; Robitussin Maximum Strength Cough Suppressant; Robitussin Pediatric; Robitussin Pediatric Cough Suppressant; Sucrets 4 Hour Cough Suppressant; Triaminic DM Long Lasting for Children; Trocal; Vicks 44 Cough Relief
Please add any relevant references here.