Tofenacin
Title: Tofenacin
CAS Registry Number: 15301-93-6
CAS Name: N-Methyl-2-[(2-methylphenyl)phenylmethoxy]ethanamine
Additional Names: N-methyl-2-[(o-methyl-a-phenylbenzyl)oxy]ethylamine; N-demethylorphenadrine; N-methylaminoethyl 2-methylbenzhydryl ether; phenyl-(o-tolylmethyl) methylaminoethyl ether; [2-(phenyl-o-tolylmethoxy)ethyl]methylamine; N-methyl-2-(2-methylbenzhydryloxy)ethylamine; N-methyl-2-[a-(2-tolylbenzyl)oxy]ethylamine
Molecular Formula: C17H21NO
Molecular Weight: 255.35
Percent Composition: C 79.96%, H 8.29%, N 5.49%, O 6.27%
Literature References: Metabolite of orphenadrine formed by N-demethylation. Prepn: BE 628167; Harms, US 3407258 (1963, 1968 both to Brocades-Stheeman & Pharmacia). Resolution of isomers: van der Stelt et al., Arzneim.-Forsch. 19, 2010 (1969). Physical and chemical properties: Doorenbos et al., Pharm. Weekbl. 101, 525 (1966). Pharmacology: Funcke et al., Arch. Int. Pharmacodyn. 177, 28 (1969); Den Besten et al., Arzneim.-Forsch. 20, 538 (1970). Metabolic studies: Hespe, Prins, Eur. J. Pharmacol. 8, 119 (1969); Hespe, Kafoe, ibid. 13, 113 (1970). Clinical studies: Bram, Shanmuganathan, Curr. Ther. Res. 13, 625 (1971).
Properties: Liquid, bp0.7 139-143°.
Boiling point: bp0.7 139-143°
 
Derivative Type: Hydrochloride
CAS Registry Number: 10488-36-5
Manufacturers' Codes: BS-7331
Trademarks: Elamol (Yamanouchi); Tofacine (Yamanouchi)
Molecular Formula: C17H21NO.HCl
Molecular Weight: 291.82
Percent Composition: C 69.97%, H 7.60%, N 4.80%, O 5.48%, Cl 12.15%
Properties: White to off-white crystals, mp 143-147° (Doorenbos); 147-148° (Harms). Freely soluble in water, methanol, ethanol, chloroform. Slightly sol in acetone. Practically insol in ethyl ether. LD50 in mice (mg/kg): 182 orally, 82 s.c., 58 i.p., 36.5 i.v.; in rats: 72 i.p.; in guinea pigs: 92 s.c. (Funcke).
Melting point: mp 143-147° (Doorenbos); 147-148° (Harms)
Toxicity data: LD50 in mice (mg/kg): 182 orally, 82 s.c., 58 i.p., 36.5 i.v.; in rats: 72 i.p.; in guinea pigs: 92 s.c. (Funcke)
 
Therap-Cat: Antidepressant.
Keywords: Antidepressant.
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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