Puneet Varma

Anabasine

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ATC code  none
ChemSpider  21106257
KEGG  C06180
Molar mass  162.23 g/mol
CAS Number  40774-73-0
UNII  LMS11II2LO
ChEBI  CHEBI:28986
Boiling point  270 °C
Anabasine httpsuploadwikimediaorgwikipediacommonsthu

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.

Contents

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

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. 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.

Analogs

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

  • 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

    Anabasine Wikipedia


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