Anabasine Explained

Anabasine is a pyridine and piperidine alkaloid found in the tree tobacco (Nicotiana glauca) plant, as well as in tree tobacco's close relative the common tobacco plant (Nicotiana tabacum).^[1] 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.^[2]

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.^[3] In larger amounts it is thought to be teratogenic in swine.^[4]

The intravenous LD₅₀ of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.^[5]

Analogs

B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine:^[6]

• 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane (TC-1698)
• 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane,
• and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane.

See also

• Anatabine

Notes and References

1. Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J . 6 . Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species . Molecules . 27 . 22 . 8105 . November 2022 . 36432206 . 9694777 . 10.3390/molecules27228105 . free .
2. Jacob P, Yu L, Shulgin AT, Benowitz NL . Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes . American Journal of Public Health . 89 . 5 . 731–6 . May 1999 . 10224986 . 1508721 . 10.2105/AJPH.89.5.731 .
3. Mizrachi N, Levy S, Goren ZQ . Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry . Journal of Forensic Sciences . 45 . 3 . 736–41 . May 2000 . 10.1520/JFS14761J . 10855991 .
4. Web site: Notes on Poisoning: Nicotiana tabacum . Canadian Biodiversity Information Facility . 2008-03-18 . 2008-05-01 .
5. Lee ST, Wildeboer K, Panter KE, Kem WR, Gardner DR, Molyneux RJ, Chang CW, Soti F, Pfister JA . 6 . Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine . Neurotoxicology and Teratology . 28 . 2 . 220–8 . 2006 . 16488116 . 10.1016/j.ntt.2005.12.010 .
6. Bhatti BS, Strachan JP, Breining SR, Miller CH, Tahiri P, Crooks PA, Deo N, Day CS, Caldwell WS . 6 . 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 . May 2008 . 18363376 . 10.1021/jo800028q .