Anabasine

Structural formula
General
Surname	Anabasine
other names	L - (-) - neonicotine; ( S ) - (-) - 2- (3-pyridyl) piperidine;
Molecular formula	C 10 H 14 N 2
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	621-972-8
ECHA InfoCard	100.150.777
PubChem	205586
ChemSpider	21106257
Wikidata	Q419308
properties
Molar mass	162.23 g mol −1
Physical state	liquid
density	1.05 g cm −3 (20 ° C)
Melting point	9 ° C
boiling point	270-272 ° C
Vapor pressure	3 h Pa (105 ° C)
solubility	miscible with water and most organic solvents
Refractive index	1.5430 (20 ° C)
safety instructions
H and P phrases	H: 300-310-411
	P: 301 + 310-361-302 + 350-321-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Anabasine is a chemical compound from the group of alkaloids . The compound consists of a pyridine and a piperidine ring, the piperidine ring having a stereocenter . It is structurally related to nornicotine , which has a ring narrower by one methylene group , and anatabine , whose piperidine ring has a double bond .

Occurrence

Tobacco plants

The L -form of anabasin could be detected in tobacco plants as well as in tobacco smoke .

properties

Anabasin is a yellowish liquid. It is a chiral compound that occurs naturally in tobacco plants as the ( S ) enantiomer . Anabasin has a toxic effect and, depending on the enantiomer, has a lethal dose (administered intravenously) of 11 mg / kg or 16 mg / kg in mice.

It belongs to the group of nicotinic acetylcholine receptor agonists and, in sufficient doses, can cause symptoms similar to nicotine poisoning . This can lead to death from cardiac arrest .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on anabasine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 99, ISBN 978-0-911910-00-1 .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-436.
↑ E. Späth, F. Kesztler: About the occurrence of d, l-nor-nicotine, d, l-anatabine and l-anabasine in tobacco (XII. Communication on tobacco alkaloids) , in: Chem. Ber. 1937 , 70 , 4, 704-709; doi: 10.1002 / cber.19370700421 .
↑ P. Jacob, L. Yu, AT Shulgin, NL Benowitz: Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes , in: Am. J. Public Health 1999 , 89 , 731-736.
↑ E. Broad Maier: Alkaloids: narcotics, hallucinogens and other drugs, lead compounds from nature , Vieweg + Teubner Verlag, 3rd edition, 2008, p 31: ISBN 3-8348-0531-9 .
↑ L. Stephen, K. Wildeboer, K. Panter, W. Kem, F. Gardner, R. Molyneux, C.–W. Chang, F. Soti, J. Pfister: Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine in: Neurotoxicology and Teratology , 2006 .
^ N. Mizrachi, S. Levy, Z. Goren: Fatal poisoning from nicotiana glauca leaves: identification of anabasine by gas-chromatography / mass spectrometry , in: Journal of Forensic Sciences 2000 , 45 , 736-741.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on anabasine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 99, ISBN 978-0-911910-00-1 .

[CRC90_3_436-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-436.

[spaeth-4] E. Späth, F. Kesztler: About the occurrence of d, l-nor-nicotine, d, l-anatabine and l-anabasine in tobacco (XII. Communication on tobacco alkaloids) , in: Chem. Ber. 1937 , 70 , 4, 704-709; doi: 10.1002 / cber.19370700421 .

[5] P. Jacob, L. Yu, AT Shulgin, NL Benowitz: Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes , in: Am. J. Public Health 1999 , 89 , 731-736.

[6] E. Broad Maier: Alkaloids: narcotics, hallucinogens and other drugs, lead compounds from nature , Vieweg + Teubner Verlag, 3rd edition, 2008, p 31: ISBN 3-8348-0531-9 .

[7] L. Stephen, K. Wildeboer, K. Panter, W. Kem, F. Gardner, R. Molyneux, C.–W. Chang, F. Soti, J. Pfister: Relative Toxicities and Neuromuscular Nicotinic Receptor Agonistic Potencies of Anabasine Enantiomers and Anabaseine in: Neurotoxicology and Teratology , 2006 .

[8] N. Mizrachi, S. Levy, Z. Goren: Fatal poisoning from nicotiana glauca leaves: identification of anabasine by gas-chromatography / mass spectrometry , in: Journal of Forensic Sciences 2000 , 45 , 736-741.