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Anabasine
Systematic (IUPAC) name
3-(2-piperidyl)pyridine
Identifiers
CAS number 40774-73-0
ATC code  ?
PubChem  ?
ChemSpider 21106257
Chemical data
Formula C10H14N2
Mol. mass 162.23 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Anabasine is a pyridine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, a close relative of the common tobacco plant (Nicotiana tabacum). Chemically, it is 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

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]

References

  1. ^ P. Jacob, 3rd, L. Yu, A. T. Shulgin and N. L. Benowitz (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): 731–736. doi:10.2105/AJPH.89.5.731. PMID 10224986. http://www.ajph.org/cgi/content/abstract/89/5/731.  
  2. ^ Mizrachi, N.; Levy, S.; Goren, Z. (2000). "Fatal poisoning from nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry". Journal of Forensic Sciences 45 (3): 736–741. PMID 10855991.  
  3. ^ "Notes on poisoning: Nicotiana tabacum". Canadian Biodiversity Information Facility. Government of Canada. 2008-03-18. http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=186&p_type=all&p_sci=sci&p_x=px. Retrieved 2008-05-01.  
  4. ^ Stephen, Lee; Wildeboer, Kristin; Panter, Kip; Kem, William; Gardner, Dale; Molyneux, Russell; Chang, Cheng-Wei; Soti, Ferenc; Pfister, James (2006-02-20). "Neurotoxicology and Teratology". USDA. http://www.ars.usda.gov/research/publications/Publications.htm?seq_no_115=182063&pf=1. Retrieved 2008-05-01.  
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