5935. Meteloidine

Nomenclature

CAS number: 526-13-6
[1α,3β(E),5α,6α,7α]-2-Methyl-2-butenoic acid 6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; (E)-1αH,5αH-tropane-3α,6β,7β-triol 3-(2-methylcrotonate); 3-(3,6,7-tropanetriol) tiglate; 6,7-dihydroxytropinetiglic acid ester; 6,7-dihydroxy-3-tiglyloxytropane.
C13H21NO4; mol wt 255.31.
C 61.16%, H 8.29%, N 5.49%, O 25.07%.

Description and references

From leaves of Datura meteloides DC., Solanaceae: Pyman, Reynolds, J. Chem. Soc. 93, 2077 (1908); King, ibid. 115, 487 (1919); from D. ferox L.: Evans, Wellendorf, ibid. 1959, 1406. Stereochemistry: Heusner, Z. Naturforsch. 9b, 683 (1954). Synthesis: Zeile, Heusner, Arch. Pharm. 292, 238 (1959).

Chemical structure

Properties

Flat needles from benzene, mp 141-142°. uv max: 217 nm (ε 12,200). Freely sol in alcohol, chloroform, acetone; sparingly sol in water, ether, benzene.

Derivative

Hydrobromide dihydrate.
C13H22BrNO4.2H2O; mol wt 372.25.
C 41.94%, H 7.04%, Br 21.47%, N 3.76%, O 25.79%.

Properties

Chisel-shaped needles, when anhydr, mp 250°.