1.02011-09-21 00:18:51 UTC2015-10-09 22:31:18 UTCFDB022738DextromethorphanDextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia [HMDB]Bayer Select Flu ReliefBayer Select Head & Chest ColdBayer Select Night Time ColdBenylin DMBenylin DM (TN)Cerose-DMChloraseptic DMContac Day & Night Cold/Flu Day CapletsContac Jr. Non-drowsy FormulaContac Nighttime Cold MedicineContac Severe Cold Formula Maximum StrengthContac Severe Cold Formula Non-DrowsyCoricidin SyrupCough-XD-MethorphanD-Methorphan hydrobromidedelta-MethorphanDemorphanDemorphan hydrobromideDemorphineDestrometerfanoDextromethorphan bromhydrateDextromethorphan bromideDextromethorphan hydrobromideDextromethorphan hydrobromide [BAN:JAN]Dextromethorphan hydrobromide monohydrateDextromethorphan hydrobromide OROS TabletsDextrometorphanDextromorphanDexyromethorphanDimacolDimetapp DMDrixoral CoughDrixoral Cough & CongestionDrixoral Cough & Sore ThroatEndotussin-NNEndotussin-NN PediatricHoldL-MethorphanLevomethorphanMethorateNaldecon-DXOrnex Severe Cold FormulaOrthoxicolPediaCare 1PediaCare Cough-Cold FormulaPrestwick_686Robitussin CFRobitussin Cold & CoughRobitussin Cough CalmersRobitussin DMRobitussin Maximum Strength CoughRobitussin Pediatric CoughRobitussin Pediatric Cough & ColdRobitussin Pediatric Night ReliefRomilarRondec dmRu-Tuss ExpectorantSt. Joseph Cough SyrupSudafed Cough SyrupTriaminicTrind-DMTussar DMTussi-OrganidinTussi-Organidin DM NRTussi-Organidin DM-S NRTylenol Cold and Flu Multi-SymptomTylenol Cold and Flu No DrowsinessTylenol Cold No DrowsinessTylenol Cough + Decongestant LiquidTylenol Cough LiquidTylenol Flu No Drowsiness GelcapsViro-MedC18H25NO271.3972271.193614427(1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene(1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene125-71-3[H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2CInChI=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-/m0/s1MKXZASYAUGDDCJ-JQHSSLGASA-N belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.MorphinansOrganic compoundsAlkaloids and derivativesMorphinansAromatic heteropolycyclic compoundsAlkyl aryl ethersAnisolesAralkylaminesAzacyclic compoundsBenzazocinesHydrocarbon derivativesOrganopnictogen compoundsPhenanthrenes and derivativesPiperidinesTetralinsTrialkylaminesAlkyl aryl etherAmineAnisoleAralkylamineAromatic heteropolycyclic compoundAzacycleBenzazocineBenzenoidEtherHydrocarbon derivativeMorphinanOrganic nitrogen compoundOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenanthrenePiperidineTertiary aliphatic amineTertiary amineTetralinSolidlogp3.75logs-4.50solubility8.51e-03 g/llogp3.49pka_strongest_basic9.85iupac(1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trieneaverage_mass271.3972mono_mass271.193614427smiles[H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2CformulaC18H25NOinchiInChI=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-/m0/s1inchikeyMKXZASYAUGDDCJ-JQHSSLGASA-Npolar_surface_area12.47refractivity82.56polarizability84.43rotatable_bond_count1acceptor_count2donor_count0physiological_charge1formal_charge0Specdb::NmrOneD1799Specdb::NmrTwoD1739Specdb::MsMs1840Specdb::MsMs1841Specdb::MsMs1842HMDB019204470#<Reference:0x0000555675ab9020>#<Reference:0x0000555675ab8d28>#<Reference:0x0000555675ab8aa8>#<Reference:0x0000555675ab8878>#<Reference:0x0000555675ab8620>#<Reference:0x0000555675ab8300>bitter