Anabasine

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Template:Chembox E number
Anabasine
Identifiers
3D model (JSmol)
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Properties
C10H14N2
Molar mass 162.23 g/mol
Density 1.01 g/ml
Melting point
Boiling point
Hazards
Flash point {{{value}}}
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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

Effects

Anabasine is present in trace amounts in tobacco smoke. In larger amounts it is thought to be teratogenic in swine. [1]

Pharmacology

Pharmacodynamics:

Anabasine is a nicotinic receptor agonist toxin and cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. [2]

Anabasine is a minor tobacco alkaloid which can be used as an indicator of a person's exposure to tobacco smoke.[1]

In high doses, anabasine will cause a depolarizing block of the nicotinic acetylcholine receptor, which can cause death by asystolia and toxicity.[2]

As such, its principal industrial use is as an insecticide.

Anabasine was also extensively investigated by the US Navy as part of Project CHATTER as a potential truth drug. [3]

Toxicology

As anabasine lacks the imine double bond of anabaseine, which significantly more toxic in mouse bioassay than S-anabasine (27-fold) and R-anabasine (18-fold). The relative agonistic potencies of the three alkaloids on human fetal nicotinic neuromuscular receptors were of the same rank order: anabaseine >> S-anabasine > R-anabasine. [4] A mouse bioassay was used to determine the relative lethalities of S- and R-enriched anabasine enantiomers. The intravenous LD50 of the (+)-R-anabasine rich fraction was 11±1.0 mg/kg and that of the (-)-S-anabasine-rich fraction was 16±1.0 mg/kg. The LD50 of anabaseine was 0.58±0.05 mg/kg. Anabaseine was significantly more toxic in the mouse bioassay than S-anabasine (27-fold) and R-anabasine (18-fold). The relative agonistic potencies of the three alkaloids on human fetal nicotinic neuromuscular receptors were of the same rank order: anabaseine >> S-anabasine > R-anabasine. [5]

See also

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.
  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.

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