5551. Lobeline

Nomenclature

CAS number: 90-69-7
2-[(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenylethanone; 2-[6-(β-hydroxyphenethyl)-1-methyl-2-piperidyl]acetophenone; α-lobeline; inflatine.
C22H27NO2; mol wt 337.46.
C 78.30%, H 8.06%, N 4.15%, O 9.48%.

Description and references

High affinity nicotinic ligand. From herb and seeds of Lobelia inflata L., Lobeliaceae (Indian tobacco): H. Wieland, Ber. 54, 1784 (1921). Structure: H. Wieland, O. Dragendorff, Ann. 473, 83 (1929). Synthesis: H. Wieland, I. Drishaus, ibid. 102; G. Schering, L. Winterhalder, ibid. 126. Absolute configuration: Schpf, Müller, Ann. 687, 241 (1965). Pharmacology: M. I. Damaj et al., J. Pharmacol. Exp. Ther. 282, 410 (1997). Receptor binding study: D. Flammia et al., J. Med. Chem. 42, 3726 (1999). Comprehensive description: F. J. Muhtadi, Anal. Profiles Drug Subs. 19, 261-313 (1990). Review of mechanism of action and therapeutic potential in psychostimulant abuse: L. P. Dwoskin, P. A. Crooks, Biochem. Pharmacol. 63, 89-98 (2002).

Chemical structure

Properties

Needles from alc, ether, benzene, mp 130-131°. [α]D15 43° (alc). Very slightly sol in water or in petr ether; sol in hot alcohol, or in chloroform, benzene, ether.

Derivative

Hydrochloride.

Nomenclature

CAS number: 134-63-4
C22H27NO2.HCl; mol wt 373.92.
C 70.67%, H 7.55%, N 3.75%, O 8.56%, Cl 9.48%.

Properties

Rosettes of slender needles from alcohol, mp 178-180°. [α]D20 43° (c = 2). uv max (methanol) 245, 280 nm (log ε 4.08, 3.05). One gram dissolves in 40 ml water, 12 ml alcohol; very sol in chloroform; very slightly sol in ether. Water solns are slightly acid to litmus. A 1% soln in water has a pH of 4.0-6.0.

Derivative

Sulfate.

Nomenclature

CAS number: 134-64-5
(C22H27NO2)2.H2SO4; mol wt 772.99.
C 68.37%, H 7.30%, N 3.62%, O 16.56%, S 4.15%.

Properties

Hygroscopic. Crystals from alc. [α]D20 25° (c = 2). Soluble in about 30 parts water, slightly in alcohol.

Derivative

(±)-Form.

Nomenclature

CAS number: 134-65-6
Lobelidine.

Properties

Prisms, mp 110°.

Therapeutic Category

CNS stimulant.

Therapeutic Category (Veterinary)

Has been used as a respiratory stimulant, ruminatoric.

Keywords

Respiratory Stimulant; CNS Stimulant