Anabasine is a
pyridine
Pyridine is a basic 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, weakly alkaline, water-miscible liquid w ...
and
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...
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
Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and '' Duboisia hopwoodii'') and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is use ...
. Its principal (historical) industrial use is as an
insecticide
Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed t ...
.
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
Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ner ...
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 ag ...
. 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
Asystole (New Latin, from Greek privative a "not, without" + ''systolē'' "contraction") is the absence of ventricular contractions in the context of a lethal heart arrhythmia (in contrast to an induced asystole on a cooled patient on a heart-lu ...
. 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 related ...
in swine.
The intravenous
LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in
mice
A mouse ( : mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus'' ...
, 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 anti ...
.
Analogs
B. Bhatti, et al. made some higher potency sterically strained
bicyclic 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