Lobeline

Structural formula
General
Surname	Lobeline
other names	2 - [(2 R , 6 S ) -6 - [(2 S ) -2-hydroxy-2-phenylethyl] -1-methylpiperidin-2-yl] -1-phenylethanone
Molecular formula	C 22 H 27 NO 2
Brief description	colorless solid (hydrochloride)
External identifiers / databases
EC number	202-012-3
ECHA InfoCard	100.001.830
PubChem	101616
ChemSpider	91814
DrugBank	DB05137
Wikidata	Q421905
properties
Molar mass	337.46 g mol −1
Physical state	firmly
Melting point	130-131 ° C ; 183-185 ° C (hydrochloride);
solubility	soluble in hot ethanol , chloroform and diethyl ether ; slightly soluble in water and petroleum ether ;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-331
	P: 261-301 + 310-311
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lobeline is a nicotine - like piperidine alkaloid with central and peripheral effects.

Occurrence

Indian tobacco ( Lobelia inflata ).

It occurs in the herb and seeds of Indian tobacco ( Lobelia inflata ).

properties

Lobeline is poorly soluble in water, well in hot chloroform , benzene or ether . As lobeline hydrochloride (C ₂₂ H ₂₈ ClNO ₂ , Zoolobelin , Lobron ) it is more soluble in water (25 g in 1 l of water) and also dissolves well in alcohol (83 g in 1 l of alcohol) and chloroform.

use

Lobelin was used in previous years for smoking cessation, but no controlled studies exist so that it cannot be recommended for smoking cessation.

history

The Indian tobacco , also called "refractive herb", has already been used by the Indians. They used it to treat dropsy and used it as an antisyphilitic to treat syphilis . It was later found to be effective against asthma. So it was mentioned in the drug books since 1820. In Germany, the company CH Boehringer, Ingelheim , with the participation of Heinrich Otto Wieland, carried out research into the pure preparation and in 1921 was able to bring the active ingredient onto the market as Lobelin (Ingelheim) . The great success of this breath analeptic led to intensive research, and in 1937 the Boehringer company succeeded in the large-scale, fully synthetic production of the active ingredient. This came on the market shortly before the Second World War as the drug Lobeton .

literature

Culture and Technology 4/2007 , magazine of the Deutsches Museum, ISSN 0344-5690 .

Individual evidence

↑ ^a ^b ^c ^d data sheet (-) - Lobeline hydrochloride from Sigma-Aldrich , accessed on April 8, 2011 ( PDF ).
↑ Entry on Lobelia Alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 15, 2014.
↑ ^a ^b ^c Entry on Lobelin at Vetpharm, accessed on November 23, 2011.
↑ L. Stead, J. Hughes: Lobeline for smoking cessation . Cochrane Database Syst Rev, 2000, PMID 10796490 .

[Sigma-1] ta sheet (-) - Lobeline hydrochloride from Sigma-Aldrich , accessed on April 8, 2011 ( PDF ).

[Römpp-2] Entry on Lobelia Alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 15, 2014.

[Vetpharm-3] Entry on Lobelin at Vetpharm, accessed on November 23, 2011.

[4] L. Stead, J. Hughes: Lobeline for smoking cessation . Cochrane Database Syst Rev, 2000, PMID 10796490 .