13-06740. Norlobelanine [Archived]

Nomenclature

CAS number: 6035-31-0
2,2′-(2,6-Piperidinediyl)bis[1-phenylethanone]; isolobelanine.
C21H23NO2; mol wt 321.41.
C 78.47%, H 7.21%, N 4.36%, O 9.96%.

Description and references

In herb of Lobelia inflata L., Lobeliaceae. Isoln from crude lobelanidine nitrate: Wieland et al., Ann. 473, 118 (1929). Synthesis: Schpf, Lehmann, ibid. 518, 1 (1935). Cis- and trans-isomers: Ebnther, Helv. Chim. Acta 41, 386 (1958).

Chemical structure

Properties

Crystals, mp 120-121°. Practically insol in water. Sol in alcohol, benzene, chloroform, ether, dil acids. On methylation it is converted to lobelanine.

Derivative

trans-Form.

Properties

Prisms from ethyl acetate + ether, mp 88-91°.

Derivative

trans-Form hydrochloride.
C21H23NO2.HCl; mol wt 357.87.
C 70.48%, H 6.76%, N 3.91%, O 8.94%, Cl 9.91%.

Properties

Crystals from alcohol + ether, dec 163-168°.

Status

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