1.0 2011-09-21 00:18:51 UTC 2015-10-09 22:31:18 UTC FDB022738 Dextromethorphan Dextromethorphan 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 Relief Bayer Select Head & Chest Cold Bayer Select Night Time Cold Benylin DM Benylin DM (TN) Cerose-DM Chloraseptic DM Contac Day & Night Cold/Flu Day Caplets Contac Jr. Non-drowsy Formula Contac Nighttime Cold Medicine Contac Severe Cold Formula Maximum Strength Contac Severe Cold Formula Non-Drowsy Coricidin Syrup Cough-X D-Methorphan D-Methorphan hydrobromide delta-Methorphan Demorphan Demorphan hydrobromide Demorphine Destrometerfano Dextromethorphan bromhydrate Dextromethorphan bromide Dextromethorphan hydrobromide Dextromethorphan hydrobromide [BAN:JAN] Dextromethorphan hydrobromide monohydrate Dextromethorphan hydrobromide OROS Tablets Dextrometorphan Dextromorphan Dexyromethorphan Dimacol Dimetapp DM Drixoral Cough Drixoral Cough & Congestion Drixoral Cough & Sore Throat Endotussin-NN Endotussin-NN Pediatric Hold L-Methorphan Levomethorphan Methorate Naldecon-DX Ornex Severe Cold Formula Orthoxicol PediaCare 1 PediaCare Cough-Cold Formula Prestwick_686 Robitussin CF Robitussin Cold & Cough Robitussin Cough Calmers Robitussin DM Robitussin Maximum Strength Cough Robitussin Pediatric Cough Robitussin Pediatric Cough & Cold Robitussin Pediatric Night Relief Romilar Rondec dm Ru-Tuss Expectorant St. Joseph Cough Syrup Sudafed Cough Syrup Triaminic Trind-DM Tussar DM Tussi-Organidin Tussi-Organidin DM NR Tussi-Organidin DM-S NR Tylenol Cold and Flu Multi-Symptom Tylenol Cold and Flu No Drowsiness Tylenol Cold No Drowsiness Tylenol Cough + Decongestant Liquid Tylenol Cough Liquid Tylenol Flu No Drowsiness Gelcaps Viro-Med C18H25NO 271.3972 271.193614427 (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-triene 125-71-3 [H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2C 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-/m0/s1 MKXZASYAUGDDCJ-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. Morphinans Organic compounds Alkaloids and derivatives Morphinans Aromatic heteropolycyclic compounds Alkyl aryl ethers Anisoles Aralkylamines Azacyclic compounds Benzazocines Hydrocarbon derivatives Organopnictogen compounds Phenanthrenes and derivatives Piperidines Tetralins Trialkylamines Alkyl aryl ether Amine Anisole Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzazocine Benzenoid Ether Hydrocarbon derivative Morphinan Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenanthrene Piperidine Tertiary aliphatic amine Tertiary amine Tetralin Solid logp 3.75 ALOGPS logs -4.50 ALOGPS solubility 8.51e-03 g/l ALOGPS logp 3.49 ChemAxon pka_strongest_basic 9.85 ChemAxon iupac (1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene ChemAxon average_mass 271.3972 ChemAxon mono_mass 271.193614427 ChemAxon smiles [H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2C ChemAxon formula C18H25NO ChemAxon 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-/m0/s1 ChemAxon inchikey MKXZASYAUGDDCJ-JQHSSLGASA-N ChemAxon polar_surface_area 12.47 ChemAxon refractivity 82.56 ChemAxon polarizability 84.43 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 1799 Specdb::MsMs 1840 Specdb::MsMs 1841 Specdb::MsMs 1842 Specdb::NmrTwoD 1739 HMDB01920 4470 #<Reference:0x000055ce31677fa0> #<Reference:0x000055ce31677de8> #<Reference:0x000055ce31677c30> #<Reference:0x000055ce31677a50> #<Reference:0x000055ce31677848> #<Reference:0x000055ce31677690> bitter