Anabasine

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Anabasine
Anabasin.svg
Systematic (IUPAC) name
3-(2-piperidyl)pyridine
Identifiers
CAS Number 40774-73-0 YesY
ATC code none
ChemSpider 21106257 YesY
UNII LMS11II2LO YesY
KEGG C06180 YesY
ChEBI CHEBI:28986 YesY
ChEMBL CHEMBL280963 YesY
Chemical data
Formula C10H14N2
Molecular mass 162.23 g/mol
  • n1cc(ccc1)C2CCCCN2
  • 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 YesY
  • Key:MTXSIJUGVMTTMU-UHFFFAOYSA-N YesY
  (verify)

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.[1]

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

The intravenous LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.[4]

Analogs

B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine:[5]

  • 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane,
  • 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane,
  • and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane.

References

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