Nefopam hydrochloride CAS 23327-57-3
Introduction：Basic information about Nefopam hydrochloride CAS 23327-57-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Nefopam hydrochloride Basic information
| Product Name: | Nefopam hydrochloride |
| Synonyms: | BENZOXAZOCINE HYDROCHLORIDE;LABOTEST-BB LT00159839;3,4,5,6-TETRAHYDRO-5-METHYL-1H-2,5-BENZOXAZOCINE HYDROCHLORIDE;3,4,5,6-TETRAHYDRO-5-METHYL-1-PHENYL-1H-2,5-BENZOXAZOCINE HYDROCHLORIDE;NEFOPAM HCL;NEFOPAM HYDROCHLORIDE;1H-2,5-Benzoxazocine, 3,4,5,6-tetrahydro-5-methyl-1-phenyl-, hydrochloride;NAFOPAN HCL |
| CAS: | 23327-57-3 |
| MF: | C17H20ClNO |
| MW: | 289.8 |
| EINECS: | 245-585-5 |
| Product Categories: | raw material;Other APIs;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API |
| Mol File: | 23327-57-3.mol |
Nefopam hydrochloride Chemical Properties
| Melting point | 238-242° |
| storage temp. | 2-8°C |
| solubility | H2O: soluble5mg/mL, clear |
| form | powder |
| color | white to beige |
| Water Solubility | H2O: 5mg/mL, clear |
| InChI | InChI=1S/C17H19NO.ClH/c1-18-11-12-19-17(14-7-3-2-4-8-14)16-10-6-5-9-15(16)13-18;/h2-10,17H,11-13H2,1H3;1H |
| InChIKey | CNNVSINJDJNHQK-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=CC=C2)C2=CC=CC=C2CN(C)CCO1.[H]Cl |
| CAS DataBase Reference | 23327-57-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | T |
| Risk Statements | 23/24/25 |
| Safety Statements | 36/37/39-45 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| HS Code | 2933.49.2600 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral |
| Toxicity | LD50 in mice, rats (mg/kg): 119, 178 orally; 44.5, 28 i.v. (Baltes) |
| Chemical Properties | White to Off-White Solid |
| Originator | Ajan,Kettelhack Riker,W. Germany,1976 |
| Uses | A cyclized analog of orphenadrine and diphenhydramine; representative of a new class of centrally acting skeletal muscle relaxants, the benzoxazocines. Analgesic; antidepressant. |
| Uses | Nefopam hydrochloride has been used as a standard for the quantitative determination of tramadol by gas chromatography–mass spectrometry (GC/MS). |
| Manufacturing Process | The starting material is prepared by reacting 2-benzoylbenzoic acid withthionyl chloride and then with 2-methylaminoethanol. 20.0 grams (0.07 mol)of N-(2-hydroxyethyl)-N-methyl-o-benzoylbenzamide is suspended in 100 mltetrahydrofuran and then slowly added in small portions to a solution of 5.5grams (0.14 mol) of lithium aluminum hydride in 150 ml tetrahydrofuran withcooling and stirring. The mixture is then refluxed for 18 hours, cooled andthen to it is successively added 5.5 ml water, 5.5 ml of 3.75 N sodiumhydroxide and 16 ml water. After removal of precipitated salts by filtration, thesolution remaining is concentrated under reduced pressure and the residuedried to yield 19.5 grams of crude product. Yield after conversion to thehydrochloride salt and recrystallization is 17.0 grams (89%), MP 128° to133°C. 5-methyl-1-phenyl-1,3,4,6-tetrahydro-5H-benz[f] -2,5-oxazocine is preparedas follows. 3.0 grams (0.011 mol) of 2-([N-(2-hydroxyethyl)-Nmethyl]amino)methylbenzhydrol, prepared as described above, 3.0 grams ptoluenesulfonic acid and 15 ml benzene are heated together with stirring untilall the benzene is distilled off. The residual oil is heated to 105°C and held atthis temperature for 1 hour, then cooled and dissolved in 30 ml water. Thisaqueous solution is then basified to pH 10.0 with 12 N sodium hydroxide,extracted with ether, and the extracts washed with water, dried overanhydrous sodium sulfate and the solvent removed under reduced pressure.The 2.26 grams (81%) oil remaining is converted to the hydrochloride salt, MP238° to 242°C. |
| Brand name | Acupan (3MPharmaceuticals). |
| Therapeutic Function | Muscle relaxant, Antidepressant |
| Biochem/physiol Actions | Nefopam is a centrally-acting analgesic drug of the benzoxazocine chemical class. Nefopam is a non-opioid, but has a potentiating effect on morphine and other opioids. Its mechanism of action is not certain, but may involve its action as a dopamine/serotonin/norepinephrine reuptake inhibitor. |
| Clinical Use | Analgesic for moderate pain |
| Drug interactions | Potentially hazardous interactions with other drugs Antidepressants: avoid MAOIs; tricyclics possibly increased risk of side effects. |
| Metabolism | Extensively metabolised in the liver to produce active metabolites.It is mainly excreted in the urine. About 8% of a dose is excreted via the faeces. |
Nefopam hydrochloride Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->Hydrochloric acid-->Lithium Aluminum Hydride-->2-Benzoylbenzoic acid-->2-Methylaminoethanol-->p-Toluenesulfonic acid |
