Dextromethorphan
Dextromethorphan (DXM or DM) is an
antitussive (cough suppressant) drug. It is one of the active ingredients in
many over-the-counter cold and cough medicines, such as Mucinex DM, Robitussin,
NyQuil, Dimetapp, Vicks, Coricidin, Delsym, and others, including generic
labels. Dextromethorphan has also found other uses in medicine, ranging from
pain relief to psychological applications. It is sold in syrup, tablet, spray,
and lozenge forms. In its pure form, dextromethorphan occurs as a white powder.
Systematic
(IUPAC) name
(+)-3-methoxy-17-methyl-(9α,13α,14α)-morphinan
Clinical data
Trade names : Delsym
AHFS/Drugs.com : monograph
MedlinePlus : a682492
Pregnancy cat. : A (AU) C (US)
Legal status : Pharmacy Only (S2) (AU)
OTC (US)
Routes :
Oral
Pharmacokinetic
data
Bioavailability : 11%
Metabolism : Hepatic (liver) enzymes:
major CYP2D6, minor CYP3A4, and minor CYP3A5
Half-life : 1.4–3.9 hours
Excretion : Renal
Identifiers
CAS number : 125-71-3
ATC code : R05DA09
PubChem : CID 15978238
DrugBank : DB00514
ChemSpider : 13109865
UNII : 7355X3ROTS
KEGG : D03742
ChEMBL : CHEMBL52440
Chemical data
Formula : C18H25NO
Mol. Mass : 271.4 g/mol
SMILES : O(c1ccc3c(c1)[C@@]24[C@@H]([C@H](N(CC2)C)C3)CCCC4)C
InChI : InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18
/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
Key:MKXZASYAUGDDCJ-NJAFHUGGSA-N
Physical data
Melt. Point : 111 °C (232 °F)
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