Tilidine
Title: Tilidine
CAS Registry Number: 20380-58-9
CAS Name: (1R,2S)-rel-2-(Dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylic acid ethyl ester
Additional Names: ethyl 2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylate; 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-D1-cyclohexene
Molecular Formula: C17H23NO2
Molecular Weight: 273.37
Percent Composition: C 74.69%, H 8.48%, N 5.12%, O 11.71%
Literature References: Prepn: ZA 6606476; GB 1120186; G. Satzinger, US 3557127 (1967, 1968, 1971, all to Warner-Lambert). Synthesis of 6-C14 hydrochloride: K.-O. Vollmer, F. W. Koss, Arzneim.-Forsch. 20, 990 (1970). Pharmacology and toxicity data: M. Hermann et al., ibid. 977, 983. Metabolism: K.-O. Vollmer, H. Achenbach, ibid. 24, 1237 (1974). HPLC determn in pharmaceutics: D. Zivanov-Stakic et al., Farmaco 44, 759 (1989). Clinical trial in comparison with nefopam, q.v.: J. Abeloos et al., Acta Anaesthesiol. Belg. 34, 283 (1983); in combination with naloxone, q.v.: H. Van Cauwenberge et al., Int. J. Clin. Pharmacol. Res. 12, 1 (1992).
Properties: bp0.01 95.5-96°.
Boiling point: bp0.01 95.5-96°
 
Derivative Type: Hydrochloride hemihydrate
Manufacturers' Codes: Gö-1261C; W-5759A
Trademarks: Lucayan (Corvi); Valoron (Gecke)
Molecular Formula: C17H23NO2.HCl.½H2O
Molecular Weight: 318.84
Percent Composition: C 64.04%, H 7.90%, N 4.39%, O 12.55%, Cl 11.12%
Properties: Crystals, mp 125°. Easily sol in water. LD50 (7 day) in mice, rats (mg/kg): 437.0, 417.7 i.g.; 490.0, 400.0 s.c.; 52.0, 74.1 i.v. (Herrmann).
Melting point: mp 125°
Toxicity data: LD50 (7 day) in mice, rats (mg/kg): 437.0, 417.7 i.g.; 490.0, 400.0 s.c.; 52.0, 74.1 i.v. (Herrmann)
 
Derivative Type: Hydrochloride
CAS Registry Number: 27107-79-5
Properties: Crystals from ethyl acetate-methyl ethyl ketone, mp 159°.
Melting point: mp 159°
 
Derivative Type: cis-(±)-Form
CAS Registry Number: 112244-09-4
Properties: bp0.01 97.5-98°.
Boiling point: bp0.01 97.5-98°
 
Derivative Type: cis-(±)-Hydrochloride
Molecular Formula: C17H23NO2.HCl.1½H2O
Molecular Weight: 318.84
Percent Composition: C 64.04%, H 7.90%, N 4.39%, O 12.55%, Cl 11.12%
Properties: Crystals from ethyl acetate-methyl ethyl ketone, mp 84°.
Melting point: mp 84°
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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