13-09579. Tofenacin [Archived]

Nomenclature

CAS number: 15301-93-6
N-Methyl-2-[(2-methylphenyl)phenylmethoxy]ethanamine; N-methyl-2-[(o-methyl-α-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-[α-(2-tolylbenzyl)oxy]ethylamine.
C17H21NO; mol wt 255.35.
C 79.96%, H 8.29%, N 5.49%, O 6.27%.

Description and 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).

Chemical structure

Properties

Liquid, bp0.7 139-143°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 10488-36-5
BS-7331; Elamol (Yamanouchi); Tofacine (Yamanouchi).
C17H21NO.HCl; mol wt 291.82.
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).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant

Status

This monograph has been retired and is no longer subject to revision or update.