| Identification | Back Directory | [Name]
TILIDINE HYDROCHLORIDE HEMIHYDRATE | [CAS]
27107-79-5 | [Synonyms]
DL-50
w5759a
go-1261
go1261c
valoron
tilidate
(1R,2S)-rel-
Tilidine HCl
trans-(+-)-ochlorid
valoronhydrochloride
50BP DNA LADDER;DL50
tilidinehydrochloride
TilidinHCl,Hemihydrate
MUWDJVKYGSDUSH-KPVRICSOSA-N
Tilidine hydrochloride solution
Tilidinhydrochloride,Hemihydrate
TILIDINE HYDROCHLORIDE HEMIHYDRATE
(1R,2S)-rel-Tilidine hydrochloride
dl-trans,trans-tildinehydrochloride
Tilidine Hydrochloride (1.0 mg/mL in Methanol)
ethyldl-trans-2-dimethylamino-1-phenyl-3-cyclohexene-1-carboxylate
3-cyclohexene-1-carboxylicacid,2-(dimethylamino)-1-phenyl-,ethylester,hydr
dl-trans-2-dimethylamino-1-phenyl-cyclohex-3-ene-trans-carbonicacidethyles
dl-trans-2-dimethylamino-1-phenyl-cyclohex-3-en-trans-1-carbonsaeureaethyles
(+-)-ethyl-trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylatehydro
Ethyl-trans-(+-)-2-(dimethylamino)-1-phenylcyclohex-3-en-1-carboxylathydrochlorid
ethyl trans-(±)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate hydrochloride
2-[Dimethylamino]-1-phenyl-3-cyclohexene-1-carboxylic acid, ethyl ester hydrochloride | [EINECS(EC#)]
248-226-0 | [Molecular Formula]
C17H26ClNO3 | [MDL Number]
MFCD02684014 | [MOL File]
27107-79-5.mol | [Molecular Weight]
327.85 |
| Chemical Properties | Back Directory | [Melting point ]
149-152?C | [Fp ]
9℃ | [storage temp. ]
-20°C Freezer | [solubility ]
Freely soluble in water, very soluble in methylene chloride, freely soluble in ethanol (96 per cent). | [form ]
Solid | [color ]
White to Off-White | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Chemical Properties]
TILIDINE HYDROCHLORIDE HEMIHYDRATE is White Solid
| [Originator]
Valoron,Goedecke,W. Germany,1970 | [Uses]
TILIDINE HYDROCHLORIDE HEMIHYDRATE is a controlled substance (opiate). Analgesic. It is used in clinical trial in comparison with Nefopam. Tilidine is one of the most widely used narcotics in Germany and Belgium.
| [Manufacturing Process]
In a first step, dimethylamine is reacted with crotonaldehyde to give 1-
(dimethylamino)-1,3-butadiene.
A solution of 194 grams (2 mols) of fresh-distilled 1-(dimethylamino)-1,3-
butadiene is combined at room temperature in a 1 liter round-bottom flask
with 352 grams (2 mols) atropic acid ethyl ester. After being stirred for about
10 minutes, the reaction mixture gradually becomes exothermic. By cooling
with ice water, the contents of the flask are kept at a temperature of 40° to
60°C. After the reaction has ceased, the mixture is kept overnight (about 8 to 24 hours) at room temperature. The next day the viscous product is dissolved
in 10 liters of ether and precipitated with ethereal hydrogen chloride forming
the corresponding hydrochloride. By fractional crystallization from ethyl
acetate/methyl ethyl ketone (10:1), an almost complete separation of the
isomeric cis/trans isomers (I) and (II) is achieved. The separation can be
carried out very easily due to the low solubility of the 1 1/2-hydrate of (I).
Therefore, during the crystallization a sufficient quantity of water for the
formation of the 1 1/2-hydrate of (I) is added to the mixture of solvents,
whereby (I) readily precipitates.
Isomer (I): 4-phenyl-3-cis-dimethylamino-4-cis-carbethoxy-?1-
cyclohexenehydrochloride, [ethyl-cis-3-(dimethylamino)-4-phenyl-1-
cyclohexene-4-carboxylate hydrochloride] , MP 84°C (the free base boils at
97.5° to 98°C at 0.01 mm pressure), 64.4% yield.
Isomer (II): 4-phenyl-3-trans-dimethylamino-4-trans-carbethoxy-?1-
cyclohexenehydrochloride, [ethyl-trans-3-(dimethylamino)-4-phenyl-1-
cyclohexene-4-carboxylate hydrochloride], MP 159°C (the free base boils at
95.5° to 96°C at 0.01 mm pressure), 22.2% yield. | [Therapeutic Function]
Analgesic |
|