Dimethylthiambutene
Title: Dimethylthiambutene
CAS Registry Number: 524-84-5
CAS Name: N,N-Dimethyl-4,4-di-2-thienyl-3-buten-2-amine
Additional Names: N,N,1-trimethyl-3,3-di-2-thienylallylamine; 3-dimethylamino-1,1-bis(2-thienyl)-1-butene; 3-dimethylamino-1,1-di(2¢-thienyl)but-1-ene
Manufacturers' Codes: 338C48; NIH-4542
Trademarks: Ohton; Aminobutene; Dimethibutin; Kobaton; Takaton
Molecular Formula: C14H17NS2
Molecular Weight: 263.42
Percent Composition: C 63.83%, H 6.50%, N 5.32%, S 24.35%
Literature References: Prepn: Grignard reaction of ethyl b-dimethylaminobutyrate with 2-thienyllithium and dehydration of the resulting 3-dimethylamino-1,1-di-2-thienylbutanol with HCl: Adamson, J. Chem. Soc. 1950, 885; US 2561899 (1951 to Burroughs Wellcome); GB 657301 (1951 to Wellcome Foundation). Toxicity data: Y. Kase et al., Chem. Pharm. Bull. 7, 372 (1959).
Properties: Viscous, dark brown or yellow oil, bp0.05 123-125°; bp3 157-158°. Sol in chloroform, ether. LD50 in mice (mg/10 kg): 1.21 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase).
Boiling point: bp0.05 123-125°; bp3 157-158°
Toxicity data: LD50 in mice (mg/10 kg): 1.21 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase)
 
Derivative Type: Hydrochloride
Molecular Formula: C14H18ClNS2
Molecular Weight: 299.88
Percent Composition: C 56.07%, H 6.05%, Cl 11.82%, N 4.67%, S 21.39%
Properties: May be recrystallized from mixt of ethyl acetate and ethanol, mp 168-169°. Sol in water, chloroform. LD50 in mice (mg/10 kg): 1.37 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase).
Melting point: mp 168-169°
Toxicity data: LD50 in mice (mg/10 kg): 1.37 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase)
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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