Lobeline
Title: Lobeline
CAS Registry Number: 90-69-7
CAS Name: 2-[(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenylethanone
Additional Names: 2-[6-(b-hydroxyphenethyl)-1-methyl-2-piperidyl]acetophenone; a-lobeline; inflatine
Molecular Formula: C22H27NO2
Molecular Weight: 337.46
Percent Composition: C 78.30%, H 8.06%, N 4.15%, O 9.48%
Literature 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: Schöpf, 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).
Properties: Needles from alc, ether, benzene, mp 130-131°. [a]D15 -43° (alc). Very slightly sol in water or in petr ether; sol in hot alcohol, or in chloroform, benzene, ether.
Melting point: mp 130-131°
Optical Rotation: [a]D15 -43° (alc)
 
Derivative Type: Hydrochloride
CAS Registry Number: 134-63-4
Molecular Formula: C22H27NO2.HCl
Molecular Weight: 373.92
Percent Composition: 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°. [a]D20 -43° (c = 2). uv max (methanol) 245, 280 nm (log e 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.
Melting point: mp 178-180°
Optical Rotation: [a]D20 -43° (c = 2)
Absorption maximum: uv max (methanol) 245, 280 nm (log e 4.08, 3.05)
 
Derivative Type: Sulfate
CAS Registry Number: 134-64-5
Molecular Formula: (C22H27NO2)2.H2SO4
Molecular Weight: 772.99
Percent Composition: C 68.37%, H 7.30%, N 3.62%, O 16.56%, S 4.15%
Properties: Hygroscopic. Crystals from alc. [a]D20 -25° (c = 2). Soluble in about 30 parts water, slightly in alcohol.
Optical Rotation: [a]D20 -25° (c = 2)
 
Derivative Type: (±)-Form
CAS Registry Number: 134-65-6
Additional Names: Lobelidine
Properties: Prisms, mp 110°.
Melting point: mp 110°
 
Therap-Cat: CNS stimulant.
Therap-Cat-Vet: Has been used as a respiratory stimulant, ruminatoric.
Keywords: Respiratory Stimulant; CNS Stimulant.

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