Anabasine
5659894
221032839
2008-06-22T19:25:34Z
Eschenmoser
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interwiki
{{Chembox new
| Name = Anabasine
| ImageFile = Anabasine.svg
<!-- | ImageSize = 200px -->
| ImageName = Chemical structure of anabasine
| Section1 = {{Chembox Identifiers
| CASNo = 40774-73-0
| SMILES = [H][C@@]2(N(C)CCC2)c1cccnc1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>10</sub>H<sub>14</sub>N<sub>2</sub>
| 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 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 [[Teratology|teratogenic]] in swine.<ref>{{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}}</ref>
==Pharmacology==
Anabasine is a [[nicotinic receptor]] [[agonist]] toxin and [[cholinesterase inhibitor]] which acts upon the [[nicotinic acetylcholine receptor]]s. Anabasine is a minor tobacco alkaloid which can be used as an indicator of a person's exposure to tobacco smoke.<ref>{{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}}</ref>
In high doses, anabasine will cause a [[depolarizing block]] of the nicotinic acetylcholine receptor, which can cause death by [[asystolia]] and [[Nicotine Poisoning|toxicity]].<ref>{{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}}</ref> 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]].<ref>{{cite web
| title = Records on Project Chatter
| work = [[Central Intelligence Agency]]
| date = 2001-05-04
| url = http://www.blackvault.com/documents/biologicalweapons/chatter/ciachatter.pdf
| accessdate = 2008-05-01}}</ref>
==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.<ref name="usda">{{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 = [[United States Department of Agriculture|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}}</ref>
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.<ref name="usda"/>
==See also==
*[[Psychoactive drug]]
*[[Addiction]]
*[[Nicotine poisoning]]
==References==
{{reflist}}
[[Category:Alkaloids]]
[[Category:Health risks]]
[[Category:Pyridines]]
[[Category:Nicotinic agonists]]
[[Category:Tobacco]]
[[Category:Plant toxin insecticides]]
[[Category:Piperidines]]
[[de:Anabasin]]
[[ja:アナバシン]]
[[ru:Анабазин]]