Anabasine

Not to be confused with Anabaseine.

Anabasine is a pyridine and piperidine alkaloid found in the tree tobacco (Nicotiana glauca) plant, as well as in tree tobacco's close relative the common tobacco plant (Nicotiana tabacum).^[1] It is a structural isomer of, and chemically similar to, nicotine. It has been used as an insecticide.

Anabasine

Clinical data
ATC code	none
Identifiers
IUPAC name 3-(2-piperidyl)pyridine
CAS Number	494-52-0 Y
ChemSpider	21106257 Y
UNII	LMS11II2LO
KEGG	C06180 Y
ChEBI	CHEBI:28986 Y
ChEMBL	ChEMBL280963 Y
CompTox Dashboard (EPA)	DTXSID9041607
ECHA InfoCard	100.007.084 100.150.777, 100.007.084
Chemical and physical data
Formula	C10H14N2
Molar mass	162.236 g·mol−1
3D model (JSmol)	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
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Anabasine is present in trace amounts in tobacco smoke, and can be used as an indicator of a person's exposure to tobacco smoke.^[2]

Pharmacology

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.^[3] In larger amounts it is thought to be teratogenic in swine.^[4]

The intravenous LD₅₀ of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.^[5]

Analogs

B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine such as 2-(pyridin-3-yl)-1-azabicyclo[3.2.2]nonane (TC-1698)^[6]

See also

• Anatabine