Anabasine

Anabasine

Clinical data
ATC code	none
Identifiers
IUPAC name 3-(2-piperidyl)pyridine
CAS Number	40774-73-0 Y
ChemSpider	21106257 Y
UNII	LMS11II2LO
KEGG	C06180 Y
ChEBI	CHEBI:28986 Y
ChEMBL	CHEMBL280963 Y
ECHA InfoCard	100.150.777
Chemical and physical data
Formula	C10H14N2
Molar mass	162.23 g/mol
3D model (Jmol)	Interactive image
SMILES n1cc(ccc1)C2CCCCN2
InChI InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2 Y Key:MTXSIJUGVMTTMU-UHFFFAOYSA-N Y

Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, a close relative of the common tobacco plant (Nicotiana tabacum). It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide.

Anabasine is present in trace amounts in tobacco smoke, and can be used as an indicator of a person's exposure to tobacco smoke.

Anabasine is a nicotinic acetylcholine receptor agonist. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of nicotine poisoning and, ultimately, death by asystole. In larger amounts it is thought to be teratogenic in swine.

The intravenous LD₅₀ of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.

B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine: