Anabasine

Chemical compound From Wikipedia, the free encyclopedia

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.

ATC code
  • none
Quick facts Clinical data, ATC code ...
Anabasine
Clinical data
ATC code
  • none
Identifiers
  • 3-(2-piperidyl)pyridine
CAS Number
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.084 100.150.777, 100.007.084 Edit this at Wikidata
Chemical and physical data
FormulaC10H14N2
Molar mass162.236 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:MTXSIJUGVMTTMU-UHFFFAOYSA-N checkY
  (verify)
Close

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

References

Related Articles

Wikiwand AI