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 with a d ...

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 ''Nicotiana glauca'' is a species of flowering plant in the tobacco genus Nicotiana of the nightshade family Solanaceae. It is known by the common name tree tobacco. Its leaves are attached to the stalk by Petiole (botany), petioles (many other ' ...

'') 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 bet ...

''). It is a structural isomer of, and chemically similar to,

nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...

. 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 to b ...

. 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 ne ...

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 In biology, depolarization or hypopolarization is a change within a cell, during which the cell undergoes a shift in electric charge distribution, resulting in less negative charge inside the cell compared to the outside. Depolarization is esse ...

of nerve transmission, which can cause symptoms similar to those of

nicotine poisoning Nicotine poisoning describes the symptoms of the toxic effects of nicotine following ingestion, inhalation, or skin contact. Nicotine poisoning can potentially be deadly, though serious or fatal overdoses are rare. Historically, most cases of nicot ...

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-lun ...

. 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 t ...

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 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 (all ...

analogs of anabasine: *2-(Pyridin-3-yl)-1-azabicyclo .2.2onane (

TC-1698 TC-1698 is a drug developed by Targacept which acts as a partial agonist for the α7 subtype of neural nicotinic acetylcholine receptors. It has neuroprotective effects in animal studies, and has been used as a lead compound to find further pot ...

) *2-(Pyridin-3-yl)-1-azabicyclo .2.2ctane, *and 2-(Pyridin-3-yl)-1-azabicyclo .2.1ctane.

References

{{Nicotinic acetylcholine receptor modulators Pyridine alkaloids Nicotinic agonists Alkaloids found in Nicotiana Plant toxin insecticides Piperidine alkaloids Plant toxins 3-Pyridyl compounds

Pharmacology

Analogs

See also

References