9434. Tigloidine

Nomenclature

CAS number: 495-83-0
2-Methyl-2-butenoic acid [1α,3α(E),5α]- 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; (E)-1αH,5αH-tropan-3β-ol 2-methylcrotonate; tiglylpseudotropeine; 3β-tigloyloxytropane; tiglic acid ester with pseudotropine.
C13H21NO2; mol wt 223.31.
C 69.92%, H 9.48%, N 6.27%, O 14.33%.

Description and references

Isoln from Duboisia myoporoides R. Br., Solanaceae and prepn from tropine and tigloyl chloride: Barger et al., J. Chem. Soc. 1937, 1820; isoln from Datura innoxia Miller, Solanaceae: Evans, Wellendorf, ibid. 1959, 1406. Pharmacology: Sanghvi et al., Eur. J. Pharmacol. 4, 246 (1968).

Chemical structure

Derivative

Hydrobromide.

Nomenclature

Tiglyssin (BDH).
C13H21NO2.HBr; mol wt 304.22.
C 51.32%, H 7.29%, N 4.60%, O 10.52%, Br 26.27%.

Properties

mp 234-235°. Soluble in chloroform.

Therapeutic Category

Antispasmodic.

Keywords

Antispasmodic