Anabasine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Anabasine
Anabasin.svg
Systematic (IUPAC) name
3-(2-piperidyl)pyridine
Clinical data
Legal status
?
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 
Mol. mass 162.23 g/mol
 YesY (what is this?)  (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 antagonist. 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 1508721. 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.  edit