| Identification | Back Directory | [Name]
tofenacin hydrochloride | [CAS]
10488-36-5 | [Synonyms]
Elamol
BS 7331
Tofacine
NSC 113809
NSC 169432
Orphenadrine USP RC C
tofenacin hydrochloride
Tofenacine hydrochloride
N-Desmethylorphenadrine Hydrochlori
Orphenadrine Related Compound C (20 mg)
Orphenadrine Impurity 8 (Orphenadrine USP RC C)
Orphenadrine Related Compound C as Hydrochloride
Orphenadrine USP Related Compound C as Hydrochloride
N-Methyl-2-[(2-methylphenyl)phenylmethoxy]ethanamine hydrochloride
Tofenacin HCl (Orphenadrine USP Related Compound C HCl, N-Desmethyl Orphenadrine HCl)
Orphenadrine Related Compound C (20 mg) (N-methyl-[2-(2-methylbenhydryloxy)ethyl]amine hydrochloride)
Orphenadrine Related Compound C (N-methyl-[2-(2-methylbenzhydryloxy)ethyl]amine hydrochloride) (1479031) | [EINECS(EC#)]
234-011-9 | [Molecular Formula]
C17H21NO.ClH | [MDL Number]
MFCD00242926 | [MOL File]
10488-36-5.mol | [Molecular Weight]
291.82 |
| Chemical Properties | Back Directory | [Melting point ]
147-148℃ (ethanol ethyl ether ) | [storage temp. ]
2-30°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Light Beige |
| Safety Data | Back Directory | [HS Code ]
2922190900 | [Toxicity]
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) |
| Hazard Information | Back Directory | [Originator]
Elamol,Brocades,UK,1971 | [Uses]
A metabolite of Orphenadrine (O695300). An antidepressant prodrug. Ondansetron USP Related Compound C. | [Manufacturing Process]
A mixture of 39.5 grams of 2-methylbenzhydrol, 200 ml of β-chloroethanol
and 10 ml of concentrated hydrochloric acid is boiled under reflux for 4 hours.
After cooling, the reaction mixture is poured into water and extracted with
petroleum ether (boiling range 40° to 60°C). The layers are separated and the
ethereal solution dried with sodium sulfate. It is then filtered. The filtrate is
concentrated by evaporation of the solvent. The residue is distilled under
reduced pressure to give 51.0 grams (yield 98%) of β-chloroethyl-2-
methylbenzhydryl ether, boiling at 156° to 158°C/2.5 mm.
A mixture of 51 grams of β-chloroethyl-2-methylbenzhydryl ether and 35
grams of methylamine in 140 ml of methanol is heated for 6 hours in a closed
vessel at a temperature of 125° to 135°C. After cooling, the reaction mixture
is poured into water and extracted with petroleum ether (boiling range 40° to
60°C). The ether layer is separated and washed with a 2 N hydrochloric acid
solution. The acidic layer is made alkaline and extracted with ether. The
ethereal solution is separated and dried with sodium sulfate. After filtration,
the solvent is evaporated and the residue distilled under reduced pressure.
There is thus obtained 40 grams (yield 80%) of N-methylaminoethyl-2-
methylbenzhydrylether boiling at 139° to 143°C/0.7 mm.
The base is dissolved in anhydrous ether, and an ethereal solution of
hydrochloric acid is added to form the hydrochloride of N-methylaminoethyl-2-
methylbenzhydryl ether. The salt is crystallized from a mixture of ethanol and
ether. Yield is 36 grams (78%); melting point 147° to 148°C. | [Brand name]
Tofenacin is INN and
BAN. | [Therapeutic Function]
Psychostimulant |
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Alfa Chemistry
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Whyte Chemicals
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