Dextromethorphan CAS 125-71-3
Introduction：Basic information about Dextromethorphan CAS 125-71-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Dextromethorphan Basic information
| Product Name: | Dextromethorphan |
| Synonyms: | D-methorphan;Methorphan;Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-;Racemethorphan [as d-form];[9α,13α,14α,(+)]-3-Methoxy-17-methylmorphinan;C06947;Dextrometorphan;(+)-3-methoxy-N-methylmorphinan |
| CAS: | 125-71-3 |
| MF: | C18H25NO |
| MW: | 271.4 |
| EINECS: | 204-752-2 |
| Product Categories: | 125-71-3 |
| Mol File: | 125-71-3.mol |
Dextromethorphan Chemical Properties
| Melting point | 80 °C |
| Boiling point | 414.48°C (rough estimate) |
| density | 1.0115 (rough estimate) |
| refractive index | 1.5740 (estimate) |
| Fp | 9℃ |
| storage temp. | -20°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | pKa 8.3 (Uncertain) |
| form | Solid |
| color | White to Off-White |
| Water Solubility | 12mg/L(temperature not stated) |
| Major Application | pharmaceutical (small molecule) |
| 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 |
| InChIKey | MKXZASYAUGDDCJ-CGTJXYLNSA-N |
| SMILES | N1([C@@H]2[C@@H]3[C@@](CC1)(CCCC3)c4c(ccc(c4)OC)C2)C |
| CAS DataBase Reference | 125-71-3(CAS DataBase Reference) |
| EPA Substance Registry System | Morphinan, 3-methoxy-17-methyl-, (9?,13?,14?)- (125-71-3) |
Safety Information
| Hazard Codes | F,T |
| Risk Statements | 11-23/24/25-39/23/24/25 |
| Safety Statements | 16-36/37-45 |
| RIDADR | 3249 |
| WGK Germany | 1 |
| RTECS | QD0194000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 2933492250 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Aquatic Chronic 2 |
| Hazardous Substances Data | 125-71-3(Hazardous Substances Data) |
| Toxicity | LD50 oral in rat: 116mg/kg |
| Description | Dextromethorphan is an over-the-counter drug that is sold alone and in combination with other products as a cough suppressant for children and adults. We have previously recommended dextromethorphan as a safe and effective cough suppressant for both children and adults. However, the weight of the evidence now suggests that dextromethorphan is no more effective than an inactive placebo syrup in suppressing a nighttime cough in children. It is the disomer of the potent opiate analgesic 3-methoxyN-methylmorphine (levorphanol). Although dextromethorphan is structurally related to opioids, it is devoid of analgesic or sedative effects at therapeutic doses. Dextromethorphan is metabolized by CYP2D6 to a more potent metabolite, dextrorphan. Dextrorphan is a stronger noncompetitive antagonist than dextromethorphan for the N-methyl-D-aspartate (NMDA) glutamate receptor.These properties promote its use in treatment of neuropathic and postoperative pain management. |
| Chemical Properties | Dextromethorphan is a white to slightly yellow, odorless, crystalline powder. The hydrobromide salt of dextromethorphan occurs as white crystals or a white crystalline powder, soluble in water, alcohol, and chloroform. It acts upon the central nervous system to suppress the cough reflex. |
| Uses | Dextromethorphan is used therapeutically as an over-thecountercough suppressant and antitussive. It is also commonlyabused particularly by adolescents because of its relative ease ofavailability. |
| Indications | Dextromethorphan is used in treating nonproductive cough. It is available widely in a variety of nonprescription forms, such as capsules, lozenges, syrups, extended-release oral suspension, and chewable tablets. This drug possesses a pronounced anticough effect and minimal action on the CNS. It is not addictive. |
| Definition | ChEBI: Dextromethorphan is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough. It has a role as a NMDA receptor antagonist, a neurotoxin, a xenobiotic, an environmental contaminant, an antitussive, a prodrug and a oneirogen. It is functionally related to a dextrorphan. It is an enantiomer of a levomethorphan. |
| Brand name | Benylin DM(Parke-Davis); Dextromethorphan Hydrobromide OROSTablets (Ciba-Geigy); Drixoral Cough (Schering-Plough HealthCare); PediaCare 1 (McNeil Consumer); Romilar(Hoffmann-LaRoche-International); St. Joseph Cough Syrup(Schering-Plough HealthCare);Agrippol;Dextophan;Dextrophen. |
| Biological Functions | Dextromethorphan hydrobromide is the D-isomer oflevorphanol. It lacks CNS activity but acts at the coughcenter in the medulla to produce an antitussive effect. Itis half as potent as codeine as an antitussive. Anecdotalreports of abuse exist, but studies of abuse potential arelacking. It has few side effects but does potentiate theactivity of monoamine oxidase inhibitors, leading to hypotensionand infrequently coma. Dextromethorphan isoften combined in lozenges with the local anestheticbenzocaine, which blocks pain from throat irritationdue to coughing. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 30, p. 1769, 1965 DOI: 10.1021/jo01017a014 |
| General Description | Dextromethorphan is the dextrorotatory form of levorphanolwith a methoxy group on the 3-position. It is availablein more than 140 over-the-counter (OTC) cough and coldformulations. Evidence-based reviews have been unable toconclude that it is more effective than placebo in reducingcough. Like (+) and (-) levorphanol, (+) dextromethorphanis a potent NMDA antagonist and, in higher than recommendeddoses, has the potential for causing dissociativeanesthetic effects similar to ketamine or phencyclidine (PCP).The OTC status and availability of pure dextromethorphanpowder online has contributed greatly to its abuse in recentyears. DAWN reports that in 2004, there were approximately12,500 emergency room visits involving dextromethorphanwith 44% of those involving abuse of the drug. The 2006National Survey on Drug Abuse report shows that nearly 1million persons aged 12 to 25 years (1.7%) misused OTCcough and cold medications in the past year. Dextromethorphan’s ability to antagonize the NMDA receptorhas led to its use to treat phantom pain, diabetic neuropathy,and postoperative acute pain. |
| Pharmacokinetics | Dextromethorphan is absorbed rapidly from the GI tract, with antitussive activity occurring within 15 to 30 minutes. It undergoes extensive hepatic metabolism. Excretion is mainly renal, with some drug eliminated unchanged but most eliminated as metabolites. Dextromethorphan is related chemically to the opiate agonists and can suppress coughing as effectively as narcotics. Cough suppression occurs by several mechanisms, but mainly the drug directly affects the cough center in the medulla. Therapeutic doses do not affect ciliary activity. |
| Side effects | Although adverse effects are generally rare, dextromethorphan toxicity can occur and is characterized by nausea and vomiting, drowsiness, dizziness, irritability, and restlessness. In excessive doses, dextromethorphan poisoning may occur and induce symptoms similar to those associated with phencyclidine. |
| Safety | Despite the safety of dextromethorphan when used at the recommended dosage (<120 mg/day), higher doses can result in nausea, vomiting, seizure, loss of consciousness, irregular heartbeat, and death. Serotonin syndrome may develop in patients on other serotonergic drugs, due to additive inhibition of serotonin reuptake by dextromethorphan. Patients with genetic variations in CYP2D6, causing rapid metabolism of dextromethorphan, may present with greater clinical effects. |
| Synthesis | Dextromethorphan, (9|á,13|á,14|á)-3-methoxy-17-methylmorphinane(23.2.1), is synthesized from ()-3-hydroxy-N-methylmorphinane by methylating the phenolhydroxyl group using phenyltrimethylammonium chloride and sodium methoxide inmethanol. The resulting racemic product ()-3-methoxy-N-methylmorphinane is separatedinto isomers using D-tartaric acid, which produces dextromethor-phan. |
| Environmental Fate | Dextromethorphan is the D-isomer of the codeine analog,methorphan. Unlike the L-isomer, it has no analgesic oraddictive properties and does not act through the opioidreceptors. The exact mechanism for the antitussive effect bydextromethorphan remains unclear and is likely multifactorial.Dextromethorphan is known to be an N-methyl-D-aspartate(NMDA) receptor antagonist; however, dextromethorphanbinding sites are not limited to the known distribution ofNMDA receptors. Dextromethorphan’s main metabolite, dextrorphan, hasNMDA receptor antagonist properties similar to ketamine andphencyclidine. This NMDA receptor antagonism is believed toresult in a decreased reuptake of catecholamines. Dextromethorphanalso inhibits the reuptake of serotonin. Theseproperties make dextromethorphan have a high abuse andmisuse potential. Dextromethorphan is a common ingredient in over-thecountercough and cold preparations, and is often combinedwith other agents including concurrent antihistamines,decongestants, analgesics, and ethanol. Patients may exhibittoxicity due to these coingestants. |
Dextromethorphan Preparation Products And Raw materials
| Raw materials | Trimethylphenylammonium chloride-->D-(-)-Tartaric Acid-->Sodium Methoxide |
