Title: Mephenesin
CAS Registry Number: 59-47-2
CAS Name: 3-(2-Methylphenoxy)-1,2-propanediol
Additional Names: 3-(o-tolyloxy)-1,2-propanediol; 1,2-dihydroxy-3-(2-methylphenoxy)propane; a-(o-tolyl)glyceryl ether; glyceryl o-tolyl ether; o-cresyl glycerol ether; cresoxypropanediol; cresoxydiol; a:b-dihydroxy-g-(2-methylphenoxy)propane
Manufacturers' Codes: BDH-312
Trademarks: Atensin; Avosyl; Avoxyl; Curythan; Daserol; Decontractyl; Dioloxol (Reed & Carnrick); Glyotol; Glykresin; Lissephen (Abbott); Memphenesin; Mepherol; Mephesin; Mephson; Mervaldin (Lannett); Myanesin (BDH); Myanol; Myodetensine; Myolysin; Myopan; Myoserol; Myoten (Central Pharm.); Oranixon (Organon); Prolax; Relaxar; Relaxil; Renarcol; Rhex (Hobein); Sansdolor; Sinan; Spasmolyn; Stilalgin; Thoxidil; Tolansin; Tolcil; Tolhart; Tolosate; Toloxyn; Tolserol (BMS); Tolulexin; Tolulox; Tolyspaz (Conal); Walconesin
Molecular Formula: C10H14O3
Molecular Weight: 182.22
Percent Composition: C 65.91%, H 7.74%, O 26.34%
Literature References: Prepn: P. Morch, Arch. Pharm. Chemi 54, 327 (1947), C.A. 42, 2058 (1948); GB 589821 (1947 to Carroll and Boake Roberts); of the carbamate: W. A. Lott, E. Pribyl, US 2609386 (1952 to Squibb). Pharmacology: F. M. Berger, W. Bradley, Br. J. Pharmacol. 1, 265 (1946); and toxicity data: P. E. Dresel, I. H. Slater, Proc. Soc. Exp. Biol. Med. 79, 286 (1952); A. P. Roszkowski, J. Pharmacol. Exp. Ther. 129, 75 (1960).
Properties: Crystals. Bitter taste. Produces numbness of the tongue. mp 70-71°. uv max (0.005% aq soln): 270 nm (E 0.395). Freely sol in alcohol, propylene glycol, chloroform. At 20° one part dissolves in 85 parts water, in 11 parts ether. Urea and its derivatives, particularly urethan, increase the water soly. One part dissolves in 60 parts of 5% urethan soln, in 40 parts of 10%, in 4.5 parts of 25%. Aq solns are stable, can be sterilized by heating, and are compatible and freely miscible with solns of sodium chloride, glucose, and derivatives of barbituric and thiobarbituric acids. pH of satd aq soln ~6. LD50 in mice, rats, hamsters (mg/kg): 471, 283, 322 i.p.; 990, 945, 821 orally (Roszkowski). LD50 in mice (mM/kg): 2.83 i.p.; 10.53 orally (Dresel, Slater).
Melting point: mp 70-71°
Absorption maximum: uv max (0.005% aq soln): 270 nm (E 0.395)
Toxicity data: LD50 in mice, rats, hamsters (mg/kg): 471, 283, 322 i.p.; 990, 945, 821 orally (Roszkowski); LD50 in mice (mM/kg): 2.83 i.p.; 10.53 orally (Dresel, Slater)
Derivative Type: Carbamate
CAS Registry Number: 533-06-2
Trademarks: Tolseram (BMS)
Molecular Formula: C11H15NO4
Molecular Weight: 225.24
Percent Composition: C 58.66%, H 6.71%, N 6.22%, O 28.41%
Properties: Crystals from water, mp about 93°. (Also a hemihydrate, mp 80-84°.) uv max (ethanol): 271, 277 nm (A1%1cm 72.7, 64.1). Has a lower water-solubility and a higher oil-solubility than mephenesin. Soly in water about 0.3%, in chloroform about 2.0%. Freely sol in alcohol. LD50 in mice (mM/kg): 2.77 i.p.; 7.67 orally (Dresel, Slater).
Melting point: mp about 93°; mp 80-84°
Absorption maximum: uv max (ethanol): 271, 277 nm (A1%1cm 72.7, 64.1)
Toxicity data: LD50 in mice (mM/kg): 2.77 i.p.; 7.67 orally (Dresel, Slater)
Therap-Cat: Muscle relaxant (skeletal).
Therap-Cat-Vet: Muscle relaxant.
Keywords: Muscle Relaxant (Skeletal).

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