3260. Dimethylthiambutene

Nomenclature

CAS number: 524-84-5
N,N-Dimethyl-4,4-di-2-thienyl-3-buten-2-amine; 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; 338C48; NIH-4542; Ohton.
C14H17NS2; mol wt 263.42.
C 63.83%, H 6.50%, N 5.32%, S 24.35%.

Description and references

Prepn: Grignard reaction of ethyl β-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).

Chemical structure

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).

Derivative

Hydrochloride.
C14H18ClNS2; mol wt 299.88.
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).

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids