ChemicalBook--->CAS DataBase List--->23327-57-3

23327-57-3

23327-57-3 Structure

23327-57-3 Structure
IdentificationMore
[Name]

Nefopam hydrochloride
[CAS]

23327-57-3
[Synonyms]

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
3-methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene hydrochloride
ACUPAN
BENZOXAZOCINE HYDROCHLORIDE
LABOTEST-BB LT00159839
NEFOPAM HCL
NEFOPAM HYDROCHLORIDE
5-benzoxazocine,5-methyl-1-phenyl-3,4,5,6-tetrahydro-1h-hydrochloride
5-methyl-1-phenyl-3,4,5,6-tetrahydro-1h-2,5-benzoxazocinehydrochloride
ajan
fenazoxinehydrochloride
r738
1H-2,5-Benzoxazocine, 3,4,5,6-tetrahydro-5-methyl-1-phenyl-, hydrochloride
NAFOPAN HCL
[EINECS(EC#)]

245-585-5
[Molecular Formula]

C17H20ClNO
[MDL Number]

MFCD00012750
[Molecular Weight]

289.8
[MOL File]

23327-57-3.mol
Chemical PropertiesBack Directory
[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 DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

23/24/25
[Safety Statements ]

36/37/39-45
[RIDADR ]

3249
[WGK Germany ]

3
[HS Code ]

2933.49.2600
[REACH Registrations]

Active
[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)
Hazard InformationBack Directory
[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.
[Manufacturing Process]

The 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 name]

Acupan (3M Pharmaceuticals).
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Nefopam hydrochloride(23327-57-3)1HNMR
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