12-05578. Lobelanine [Archived]

Nomenclature

CAS number: 579-21-5
cis-2,2′-(1-Methyl-2,6-piperidinediyl)bis[1-phenylethanone]; 2,2′′-(1-methyl-2,6-piperidinediyl)diacetophenone.
C22H25NO2; mol wt 335.44.
C 78.77%, H 7.51%, N 4.18%, O 9.54%.

Description and references

After lobeline, the most abundant alkaloid of Lobelia inflata L., Lobeliaceae. Isoln: Wieland et al., Ann. 444, 40 (1925). Synthesis: Schpf, Lehmann, ibid. 518, 1 (1935); Parker et al., J. Chem. Soc. 1959, 2433.

Chemical structure

Properties

Rosettes of needles from petr ether or ether, mp 99°. Freely sol in alcohol, acetone, benzene, chloroform; slightly sol in water, ether.

Derivative

Hydrochloride.
C22H25NO2.HCl; mol wt 371.90.
C 71.05%, H 7.05%, N 3.77%, O 8.60%, Cl 9.53%.

Properties

Crystals from dil alcohol, dec 188°. Sol in chloroform; slightly sol in abs alcohol, cold water.

Derivative

Hydrobromide.
C22H25NO2.HBr; mol wt 416.35.
C 63.46%, H 6.29%, N 3.36%, O 7.69%, Br 19.19%.

Properties

Dec 188°.

Derivative

Nitrate.
C22H25NO2.HNO3; mol wt 398.45.
C 66.32%, H 6.58%, N 7.03%, O 20.08%.

Properties

mp 153-154°.

Status

This monograph has been retired and is no longer subject to revision or update.