Anabasine

Chembox new
Name = Anabasine
ImageFile = Anabasin.svg
ImageName = Chemical structure of anabasine
Section1 = Chembox Identifiers
CASNo = 40774-73-0
SMILES = [H] [C@@] 2(N(C)CCC2)c1cccnc1
Section2 = Chembox Properties
Formula = C₁₀H₁₄N₂
MolarMass = 162.23 g/mol
Density = 1.01 g/ml
MeltingPt = 9 °C
BoilingPt = 270 °C
Section7 = Chembox Hazards
FlashPt = 93 °C
ExternalMSDS = [http://www.coleparmer.com/catalog/Msds/02161.htm External MSDS]

Anabasine is a pyridine alkaloid found in the Tree Tobacco ("Nicotiana glauca") plant, a close relative of the common tobacco plant ("Nicotiana tabacum"). 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. [cite journal | author = P. Jacob, 3rd, L. Yu, A. T. Shulgin and N. L. Benowitz | title = Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes | year = 1999 | journal = Am J Public Health | volume = 89 | issue = 5 | pages = 731–736 | url = http://www.ajph.org/cgi/content/abstract/89/5/731 | pmid = 10224986]

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. [cite journal | title = Fatal poisoning from nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry | | author = Mizrachi, N.; Levy, S.; Goren, Z. | journal = Journal of Forensic Sciences | volume = 45 | issue = 3 | year = 2000 | pages = 736–741 | pmid = 10855991] In larger amounts it is thought to be teratogenic in swine. [cite web
title = Notes on poisoning: Nicotiana tabacum
work = Canadian Biodiversity Information Facility
publisher = Government of Canada
date = 2008-03-18
url = http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=186&p_type=all&p_sci=sci&p_x=px
accessdate = 2008-05-01]

The intravenous LD₅₀ of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.cite web
last = Stephen
first = Lee
coauthors = Wildeboer, Kristin; Panter, Kip; Kem, William; Gardner, Dale; Molyneux, Russell; Chang, Cheng-Wei; Soti, Ferenc; Pfister, James
title = Neurotoxicology and Teratology
publisher = USDA
date = 2006-02-20
url = http://www.ars.usda.gov/research/publications/Publications.htm?seq_no_115=182063&pf=1
accessdate = 2008-05-01]

ee also

*Psychoactive drug
*Addiction
*Nicotine poisoning

References