Anabasine is a
pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakl ...
and
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
alkaloid found in the Tree Tobacco (''
Nicotiana glauca'') plant, a close relative of the common tobacco plant (''
Nicotiana tabacum
''Nicotiana tabacum'', or cultivated tobacco, is an annually grown herbaceous plant of the '' Nicotiana'' genus. The plant is tropical in origin, is commonly grown throughout the world, and is often found in cultivation. It grows to heights be ...
''). 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.
Pharmacology
Anabasine is a
nicotinic acetylcholine receptor agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
. 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. In larger amounts it is thought to be
teratogenic
Teratology is the study of abnormalities of physiological development in organisms during their life span. It is a sub-discipline in medical genetics which focuses on the classification of congenital abnormalities in dysmorphology. The relat ...
in swine.
The intravenous
LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in
mice, depending on the
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
.
Analogs
B. Bhatti, et al. made some higher potency sterically strained
bicyclic
In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (a ...
analogs of anabasine:
*2-(Pyridin-3-yl)-1-azabicyclo
.2.2onane (
TC-1698)
*2-(Pyridin-3-yl)-1-azabicyclo
.2.2ctane,
*and 2-(Pyridin-3-yl)-1-azabicyclo
.2.1ctane.
See also
*
Anatabine
References
{{Nicotinic acetylcholine receptor modulators
Pyridine alkaloids
Nicotinic agonists
Alkaloids found in Nicotiana
Plant toxin insecticides
Piperidine alkaloids
Plant toxins
3-Pyridyl compounds