Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, as well as in the close relative of the common tobacco plant (Nicotiana tabacum).[1] It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide.
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ECHA InfoCard | 100.007.084 100.150.777, 100.007.084 |
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Formula | C10H14N2 |
Molar mass | 162.236 g·mol−1 |
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Anabasine is present in trace amounts in tobacco smoke, and can be used as an indicator of a person's exposure to tobacco smoke.[2]
Anabasine is a nicotinic acetylcholine receptor agonist. 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.[3] In larger amounts it is thought to be teratogenic in swine.[4]
The intravenous LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer.[5]
B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine:[6]