| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:31:18 UTC |
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| Update date | 2017-01-19 02:36:27 UTC |
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| FoodComEx ID | PC000554 |
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| FoodDB Record | FDB022738 |
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| Chemical Information |
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| Name | Dextromethorphan |
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| Description | 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] |
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| CAS Number | 125-71-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Bayer Select Flu Relief | hmdb | | Bayer Select Head & Chest Cold | hmdb | | Bayer Select Night Time Cold | hmdb | | Benylin DM | hmdb | | Benylin DM (TN) | hmdb | | Cerose-DM | hmdb | | Chloraseptic DM | hmdb | | Contac Day & Night Cold/Flu Day Caplets | hmdb | | Contac Jr. Non-drowsy Formula | hmdb | | Contac Nighttime Cold Medicine | hmdb | | Contac Severe Cold Formula Maximum Strength | hmdb | | Contac Severe Cold Formula Non-Drowsy | hmdb | | Coricidin Syrup | hmdb | | Cough-X | hmdb | | D-Methorphan | HMDB | | D-Methorphan hydrobromide | HMDB | | delta-Methorphan | HMDB | | Demorphan | HMDB | | Demorphan hydrobromide | HMDB | | Demorphine | HMDB | | Destrometerfano | HMDB | | Dextromethorphan bromhydrate | HMDB | | Dextromethorphan bromide | HMDB | | Dextromethorphan hydrobromide | HMDB | | Dextromethorphan hydrobromide [BAN:JAN] | hmdb | | Dextromethorphan hydrobromide monohydrate | hmdb | | Dextromethorphan hydrobromide OROS Tablets | hmdb | | Dextrometorphan | HMDB | | Dextromorphan | HMDB | | Dexyromethorphan | HMDB | | Dimacol | hmdb | | Dimetapp DM | hmdb | | Drixoral Cough | hmdb | | Drixoral Cough & Congestion | hmdb | | Drixoral Cough & Sore Throat | hmdb | | Endotussin-NN | hmdb | | Endotussin-NN Pediatric | hmdb | | Hold | hmdb | | L-Methorphan | HMDB | | Levomethorphan | HMDB | | Methorate | hmdb | | Naldecon-DX | hmdb | | Ornex Severe Cold Formula | hmdb | | Orthoxicol | hmdb | | PediaCare 1 | hmdb | | PediaCare Cough-Cold Formula | hmdb | | Prestwick_686 | hmdb | | Robitussin CF | hmdb | | Robitussin Cold & Cough | hmdb | | Robitussin Cough Calmers | hmdb | | Robitussin DM | hmdb | | Robitussin Maximum Strength Cough | hmdb | | Robitussin Pediatric Cough | hmdb | | Robitussin Pediatric Cough & Cold | hmdb | | Robitussin Pediatric Night Relief | hmdb | | Romilar | hmdb | | Rondec dm | hmdb | | Ru-Tuss Expectorant | hmdb | | St. Joseph Cough Syrup | hmdb | | Sudafed Cough Syrup | hmdb | | Triaminic | hmdb | | Trind-DM | hmdb | | Tussar DM | hmdb | | Tussi-Organidin | hmdb | | Tussi-Organidin DM NR | hmdb | | Tussi-Organidin DM-S NR | hmdb | | Tylenol Cold and Flu Multi-Symptom | hmdb | | Tylenol Cold and Flu No Drowsiness | hmdb | | Tylenol Cold No Drowsiness | hmdb | | Tylenol Cough + Decongestant Liquid | hmdb | | Tylenol Cough Liquid | hmdb | | Tylenol Flu No Drowsiness Gelcaps | hmdb | | Viro-Med | hmdb |
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| Chemical Formula | C18H25NO |
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| IUPAC name | (1S,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene |
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| InChI Identifier | 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 |
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| InChI Key | MKXZASYAUGDDCJ-JQHSSLGASA-N |
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| Isomeric SMILES | [H][C@@]12CC3=C(C=C(OC)C=C3)[C@@]3(CCCC[C@@]13[H])CCN2C |
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| Average Molecular Weight | 271.3972 |
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| Monoisotopic Molecular Weight | 271.193614427 |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Morphinans |
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| Sub Class | Not Available |
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| Direct Parent | Morphinans |
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| Alternative Parents | |
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| Substituents | - Morphinan
- Phenanthrene
- Benzazocine
- Tetralin
- Anisole
- Alkyl aryl ether
- Aralkylamine
- Piperidine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Ether
- Organoheterocyclic compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 1 g |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Toronto Research Chemicals | D299445 |
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