4380. Geissoschizoline

Nomenclature

CAS number: 18397-07-4
Curan-17-ol; pereirine.
C19H26N2O; mol wt 298.42.
C 76.47%, H 8.78%, N 9.39%, O 5.36%.

Description and references

From bark of Geissospermum vellosii Allem., Apocynaceae: Hesse, Ann. 202, 141 (1880); Bertho, Moog, ibid. 509, 241 (1934). Identity with pereirine: Bertho, Koll, Naturwissenschaften 48, 49 (1961). Structure: Janot et al., Compt. Rend. 250, 4383 (1960); Bertho, Koll Ber. 94, 2737 (1961). Synthesis: Hymon, Schmid, Helv. Chim. Acta 49, 2067 (1966); of dl-form: Dadson, Harley-Mason, Chem. Commun. 1969, 665; Harley-Mason, Taylor, ibid. 1970, 812.

Chemical structure

Properties

Coarse crystals from abs methanol, mp 142.5-143°. [α]D21 +32° (ethanol). uv max in (ethanol): 245, 300 nm (log ε 3.93, 3.47). Sol in alcohol, chloroform, ether. Practically insol in water.

Derivative

Methyl chloride.
C19H26N2O.CH3Cl; mol wt 348.91.
C 68.85%, H 8.38%, N 8.03%, O 4.59%, Cl 10.16%.

Properties

Rods from abs methanol, mp 297°.

Derivative

Methiodide.
C19H26N2O.CH3I; mol wt 440.36.
C 54.55%, H 6.64%, N 6.36%, O 3.63%, I 28.82%.

Properties

Rods from abs methanol, mp 254°.