12-05577. Lobelanidine [Archived]

Nomenclature

CAS number: 552-72-7
[2α(R*),6α(S*)]-1-Methyl-α,α′-diphenyl-2,6-piperidinediethanol; α,α′-[(1-methyl-2,6-piperidinediyl)dimethylene]dibenzyl alcohol.
C22H29NO2; mol wt 339.47.
C 77.84%, H 8.61%, N 4.13%, O 9.43%.

Description and references

From herb of Lobelia inflata L., Lobeliaceae: Wieland et al., Ann. 444, 40 (1925). Synthesis: Wieland, Drishaus, ibid. 473, 102 (1929). Comprehensive review of H. Wieland's work on Lobelia alkaloids with complete references is given by Schpf, Naturwissenschaften 30, 359 (1942).

Chemical structure

Properties

Scales from alc, mp 150°. Distills unchanged in vacuo. Freely sol in benzene, chloroform, acetone; slighty sol in ether, petr ether; almost insol in water.

Derivative

Hydrochloride.
C22H29NO2.HCl; mol wt 375.93.
C 70.29%, H 8.04%, N 3.73%, O 8.51%, Cl 9.43%.

Properties

Needles from alcohol, mp 135-138°.

Derivative

Hydrobromide.
C22H29NO2.HBr; mol wt 420.38.
C 62.86%, H 7.19%, N 3.33%, O 7.61%, Br 19.01%.

Properties

Crystals, mp 189°.

Status

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