Anabasine

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Anabasine
Anabasin.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.150.777
Chemical and physical data
Formula C10H14N2
Molar mass 162.23 g/mol
3D model (JSmol)
  (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[edit]

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[edit]

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[edit]

  1. ^ Jacob, P. 3rd.; Yu, L.; Shulgin, A. T.; Benowitz, N. L. (1999). "Minor Tobacco Alkaloids as Biomarkers for Tobacco Use: Comparison of Users of Cigarettes, Smokeless Tobacco, Cigars, and Pipes". Am J Public Health. 89 (5): 731–6. doi:10.2105/AJPH.89.5.731. PMC 1508721Freely accessible. PMID 10224986. 
  2. ^ Mizrachi, N.; Levy, S.; Goren, Z. Q. (2000). "Fatal Poisoning from Nicotiana glauca Leaves: Identification of Anabasine by Gas-Chromatography / Mass Spectrometry". Journal of Forensic Sciences. 45 (3): 736–41. PMID 10855991. 
  3. ^ "Notes on Poisoning: Nicotiana tabacum". Canadian Biodiversity Information Facility. 2008-03-18. Retrieved 2008-05-01. 
  4. ^ Lee, S. T.; Wildeboer, K.; Panter, K. E.; Kem, W. R.; Gardner, D. R.; Molyneux, R. J.; Chang, C. W.; Soti, F.; Pfister, J. A. (2006). "Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine". Neurotoxicology and Teratology. 28 (2): 220–8. doi:10.1016/j.ntt.2005.12.010. PMID 16488116. 
  5. ^ Bhatti, B.; Strachan, J.; Breining, S.; Miller, C.; Tahiri, P.; Crooks, P.; Deo, N.; Day, C.; Caldwell, W. (2008). "Synthesis of 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, a Class of Potent Nicotinic Acetylcholine Receptor-Ligands". The Journal of Organic Chemistry. 73 (9): 3497–507. doi:10.1021/jo800028q. PMID 18363376.