Anabasine is a
pyridinePyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...
alkaloidAlkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
found in the Tree Tobacco (
Nicotiana glaucaNicotiana glauca is a species of wild tobacco known by the common names tree tobacco and incorrectly also Mustard tree. Its leaves are attached to the stalk by petioles , and its leaves and stems are neither pubescent nor sticky like Nicotiana tabacum...
) plant, a close relative of the common tobacco plant (
Nicotiana tabacumNicotiana tabacum, or cultivated tobacco, is a perennial herbaceous plant. It is found only in cultivation, where it is the most commonly grown of all plants in the Nicotiana genus, and its leaves are commercially grown in many countries to be processed into tobacco. It grows to heights between 1...
). Chemically, it is similar to
nicotineNicotine is an alkaloid found in the nightshade family of plants that constitutes approximately 0.6–3.0% of the dry weight of tobacco, with biosynthesis taking place in the roots and accumulation occurring in the leaves...
. Its principal (historical) industrial use is as an
insecticideAn insecticide is a pesticide used against insects. They include ovicides and larvicides used against the eggs and larvae of insects respectively. Insecticides are used in agriculture, medicine, industry and the household. The use of insecticides is believed to be one of the major factors behind...
.
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 receptorNicotinic acetylcholine receptors, or nAChRs, are cholinergic receptors that form ligand-gated ion channels in the plasma membranes of certain neurons and on the postsynaptic side of the neuromuscular junction...
agonistAn agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
. In high doses, it produces a depolarizing block of nerve transmission, which can cause symptoms similar to those of
nicotine poisoningNicotine poisoning describes the symptoms of the toxic effects of consuming nicotine, which can potentially be deadly. Historically, most cases of nicotine poisoning have been the result of use of nicotine as an insecticide....
and, ultimately, death by
asystoleIn medicine, asystole is a state of no cardiac electrical activity, hence no contractions of the myocardium and no cardiac output or blood flow...
. In larger amounts it is thought to be
teratogenicTeratology is the study of abnormalities of physiological development. It is often thought of as the study of human birth defects, but it is much broader than that, taking in other non-birth developmental stages, including puberty; and other non-human life forms, including plants.- Etymology :The...
in swine.
The intravenous LD
50 of anabasine ranges from 11 mg/kg to 16 mg/kg in
miceA mouse is a small mammal belonging to the order of rodents. The best known mouse species is the common house mouse . It is also a popular pet. In some places, certain kinds of field mice are also common. This rodent is eaten by large birds such as hawks and eagles...
, depending on the
enantiomerIn chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
.