Nefopam hydrochloride

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 HYDROCHLORIDE;1H-2,5-Benzoxazocine, 3,4,5,6-tetrahydro-5-methyl-1-phenyl-, hydrochloride;NAFOPAN HCL;ACUPAN
CAS:23327-57-3
MF:C17H20ClNO
MW:289.8
EINECS:245-585-5
Product Categories:Other APIs;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;raw material
Mol File:23327-57-3.mol
Nefopam hydrochloride Structure
Nefopam hydrochloride Chemical Properties
Melting point 238-242°
storage temp. 2-8°C
solubility H2O: soluble5mg/mL, clear
form powder
color white to beige
CAS DataBase Reference23327-57-3(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
ToxicityLD50 in mice, rats (mg/kg): 119, 178 orally; 44.5, 28 i.v. (Baltes)
MSDS Information
Nefopam hydrochloride Usage And Synthesis
Chemical PropertiesWhite to Off-White Solid
OriginatorAjan,Kettelhack Riker,W. Germany,1976
UsesNefopam hydrochloride has been used as a standard for the quantitative determination of tramadol by gas chromatography–mass spectrometry (GC/MS).
UsesA cyclized analog of orphenadrine and diphenhydramine; representative of a new class of centrally acting skeletal muscle relaxants, the benzoxazocines. Analgesic; antidepressant.
Manufacturing ProcessThe starting material is prepared by reacting 2-benzoylbenzoic acid with thionyl chloride and then with 2-methylaminoethanol. 20.0 grams (0.07 mol) of N-(2-hydroxyethyl)-N-methyl-o-benzoylbenzamide is suspended in 100 ml tetrahydrofuran and then slowly added in small portions to a solution of 5.5 grams (0.14 mol) of lithium aluminum hydride in 150 ml tetrahydrofuran with cooling and stirring. The mixture is then refluxed for 18 hours, cooled and then to it is successively added 5.5 ml water, 5.5 ml of 3.75 N sodium hydroxide and 16 ml water. After removal of precipitated salts by filtration, the solution remaining is concentrated under reduced pressure and the residue dried to yield 19.5 grams of crude product. Yield after conversion to the hydrochloride salt and recrystallization is 17.0 grams (89%), MP 128° to 133°C.
5-methyl-1-phenyl-1,3,4,6-tetrahydro-5H-benz[f] -2,5-oxazocine is prepared as 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 until all the benzene is distilled off. The residual oil is heated to 105°C and held at this temperature for 1 hour, then cooled and dissolved in 30 ml water. This aqueous solution is then basified to pH 10.0 with 12 N sodium hydroxide, extracted with ether, and the extracts washed with water, dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The 2.26 grams (81%) oil remaining is converted to the hydrochloride salt, MP 238° to 242°C.
Brand nameAcupan (3M Pharmaceuticals).
Therapeutic FunctionMuscle relaxant, Antidepressant
Biochem/physiol ActionsNefopam 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 UseAnalgesic for moderate pain
Drug interactionsPotentially hazardous interactions with other drugs
Antidepressants: avoid MAOIs; tricyclics possibly increased risk of side effects.
MetabolismExtensively 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 materialsThionyl chloride-->Hydrochloric acid-->Lithium Aluminum Hydride-->2-Benzoylbenzoic acid-->2-Methylaminoethanol-->p-Toluenesulfonic acid
Chlorodimethylphenylsilane Levofloxacin HCL Capsule 5-Methyl-1H-benzotriazole Methyl Methyltriphenylphosphonium bromide 3-Methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene Bensulfuron methyl Topotecan hydrochloride Sibutramine hydrochloride Tramadol hydrochloride Nefopam hydrochloride Cetirizine hydrochloride Kresoxim-methyl PHENYL VALERATE 1-AdaMantanethylaMine Thiophanate-methyl Diphenhydramine Hydrochloride Trimethylphenylammonium chloride Nefopam Hcl

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