Structural Formula Vector Image
Title: Lobelanine
CAS Registry Number: 579-21-5
CAS Name: cis-2,2¢-(1-Methyl-2,6-piperidinediyl)bis[1-phenylethanone]
Additional Names: 2,2¢¢-(1-methyl-2,6-piperidinediyl)diacetophenone
Molecular Formula: C22H25NO2
Molecular Weight: 335.44
Percent Composition: C 78.77%, H 7.51%, N 4.18%, O 9.54%
Literature References: After lobeline, the most abundant alkaloid of Lobelia inflata L., Lobeliaceae. Isoln: Wieland et al., Ann. 444, 40 (1925). Synthesis: Schöpf, Lehmann, ibid. 518, 1 (1935); Parker et al., J. Chem. Soc. 1959, 2433.
Properties: Rosettes of needles from petr ether or ether, mp 99°. Freely sol in alcohol, acetone, benzene, chloroform; slightly sol in water, ether.
Melting point: mp 99°
Derivative Type: Hydrochloride
Molecular Formula: C22H25NO2.HCl
Molecular Weight: 371.90
Percent Composition: 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 Type: Hydrobromide
Molecular Formula: C22H25NO2.HBr
Molecular Weight: 416.35
Percent Composition: C 63.46%, H 6.29%, N 3.36%, O 7.69%, Br 19.19%
Properties: Dec 188°.
Derivative Type: Nitrate
Molecular Formula: C22H25NO2.HNO3
Molecular Weight: 398.45
Percent Composition: C 66.32%, H 6.58%, N 7.03%, O 20.08%
Properties: mp 153-154°.
Melting point: mp 153-154°
Status: This monograph has been retired and is no longer subject to revision or update.

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