Anabasine

Anabasine

Systematic (IUPAC) name
3-(2-piperidyl)pyridine
Identifiers
CAS Number	40774-73-0
ATC code	none
ChemSpider	21106257
UNII	LMS11II2LO
KEGG	C06180
ChEBI	CHEBI:28986
ChEMBL	CHEMBL280963
Chemical data
Formula	C10H14N2
Molar mass	162.23 g/mol
SMILES n1cc(ccc1)C2CCCCN2
InChI 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 Key:MTXSIJUGVMTTMU-UHFFFAOYSA-N
(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

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

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

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.