Lobeline

Lobeline

Systematic (IUPAC) name
2-((2R,6S)-6-((S)-2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	90-69-7 N
ATCvet code	QV04CV01 (WHO)
PubChem	CID: 101616
ChemSpider	91814 N
UNII	D0P25S3P81 Y
KEGG	D02364 Y
ChEMBL	CHEMBL2103769 Y
Chemical data
Formula	C22H27NO2
Molecular mass	337.455
SMILES O=C(C[C@@H]1N([C@@H](CCC1)C[C@@H](C2=CC=CC=C2)O)C)C3=CC=CC=C3
InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1 N Key:MXYUKLILVYORSK-HBMCJLEFSA-N N
NY (what is this?)  (verify)

Lobeline is an alkaloid found in "Indian tobacco" (Lobelia inflata), "Devil's tobacco" (Lobelia tupa), "cardinal flower" (Lobelia cardinalis), "great lobelia" (Lobelia siphilitica), and Hippobroma longiflora. Additionally, it is also found in Lobelia chinensis. In its pure form it is a white amorphous powder which is freely soluble in water.

Potential uses

Lobeline has been sold, in tablet form, for use as a smoking cessation aid, and may have application in the treatment of other drug addictions such as addiction to amphetamines, cocaine, or alcohol.

Pharmacology

Lobeline has multiple mechanisms of action, acting as a VMAT2 ligand, which stimulates dopamine release to a moderate extent when administered alone, but reduces the dopamine release caused by methamphetamine. It also inhibits the reuptake of dopamine and serotonin, and acts as a mixed agonist–antagonist at nicotinic acetylcholine receptors to which it binds at the subunit interfaces of the extracellular domain. It is also an antagonist at μ-opioid receptors.