6440. Nefopam

Nomenclature

CAS number: 13669-70-0
3,4,5,6-Tetrahydro-5-methyl-1-phenyl-1H-2,5-benzoxazocine; 5-methyl-1-phenyl-1,3,4,6-tetrahydro-5H-benz[f]-2,5-oxazocine.
C17H19NO; mol wt 253.34.
C 80.60%, H 7.56%, N 5.53%, O 6.32%.

Description and references

A cyclized analog of orphenadrine and diphenhydramine, q.q.v.; representative of a new class of centrally acting skeletal muscle relaxants, the benzoxazocines. Prepn: NL 6606390 (1966 to Rexall); M. W. Klohs et al., US 3830803 (1974 to Riker). LC-MS-MS determn in plasma: G. Hoizey et al., J. Pharm. Biomed. Anal. 42, 593 (2006). Pharmacology: Bassett et al., Br. J. Pharmacol. 37, 69 (1969); Klohs et al., Arzneim.-Forsch. 22, 132 (1972). Clinical trial as post-operative analgesic: B. Du Manoir et al., Br. J. Anaesth. 91, 836 (2003). Review of pharmacology and therapeutic efficacy: R. C. Heel et al., Drugs 19, 249-267 (1980).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 23327-57-3
Fenazoxine; R-738; Acupan (Meda); Ajan (3M).
C17H19NO.HCl; mol wt 289.80.
C 70.46%, H 6.96%, N 4.83%, O 5.52%, Cl 12.23%.

Properties

mp 238-242°. LD50 in mice, rats (mg/kg): 119, 178 orally; 44.5, 28 i.v. (Baltes).

Therapeutic Category

Analgesic.

Keywords

Analgesic; Non-opioids; Antidepressant; Bicyclics