Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca Nicotiana tabacum 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] 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 ]
^ 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 . ^ 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 . ^ "Notes on Poisoning: Nicotiana tabacum " . Canadian Biodiversity Information Facility. 2008-03-18. Retrieved 2008-05-01 . ^ 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 . ^ 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 .
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. PMID 10224986. 
