Piperidine alkaloids

Piperine is an alkaloid extracted from the plant, Piper nigrum. Responsible for the pungency of black pepper, it is used in food flavorings as a spice, in fragrances, as an insecticide, and as an animal pest repellent.

Coniine is a poisonous chemical compound, an alkaloid present in and isolable from poison hemlock (Conium maculatum), where its presence has been a source of significant economic, medical, and historico-cultural interest; coniine is also produced by the yellow pitcher plant (Sarracenia flava), and fool's parsley (Aethusa cynapium). Its ingestion and extended exposure are toxic to humans and all classes of livestock; its mechanism of poisoning involves disruption of the central nervous system, with death caused by respiratory paralysis. The biosynthesis of coniine contains as its penultimate st

Lobeline is a piperidine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco (Lobelia inflata), Devil's tobacco (Lobelia tupa), great lobelia (Lobelia siphilitica), Lobelia chinensis, and Hippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.

Anabasine is a pyridine and piperidine alkaloid found in the tree tobacco (Nicotiana glauca) plant, as well as in tree tobacco's close relative the common tobacco plant (Nicotiana tabacum). It is a structural isomer of, and chemically similar to, nicotine. It has been used as an insecticide.

Arecaidine, also known as '''N-methylguvacine''', is an alkaloid in areca nuts and a GABA reuptake inhibitor. It is structurally similar to the GABA reuptake inhibitors guvacine and nipecotic acid. Arecaidine has been found to produce sedative effects in mice and to protect against the lethality of the GABAA receptor antagonists bicuculline and pentylenetetrazol. On the other hand, it did not produce anticonvulsant effects. Lime is said to hydrolyse arecoline to arecaidine.

Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.

Conhydrine is a poisonous alkaloid found in poison hemlock (Conium maculatum) in small quantities.

Chavicine is a possibly pungent compound found in black pepper and other species of the genus Piper. It is one of the four geometric isomers of piperine.

Carpaine is the major piperidine alkaloid component of papaya leaves which has been studied for potential medicinal effects. Carpaine extracted from Carica papaya trees has been reported to have diverse biological properties, such as anti-malarial, anti-inflammatory, anti-oxidant, and vasodilatory effects. Especially, Carpaine possessed significant anti-plasmodial activity in vitro (IC50 of 0.2 μM) and high selectivity towards the parasites.

Lobelanidine is a chemical analog of lobeline.

Himbacine is an alkaloid isolated from the bark of Australian magnolias. Himbacine has been synthesized using a Diels-Alder reaction as a key step. Himbacine's activity as a muscarinic receptor antagonist, with specificity for the muscarinic acetylcholine receptor M2, made it a promising starting point in Alzheimer's disease research. The development of a muscarinic antagonist based on himbacine failed, but an analog, vorapaxar, has been approved by the FDA as a thrombin receptor antagonist.

Nupharamine is an alkaloid found in Nuphar japonica and in castoreum.

Febrifugine is a quinazolinone alkaloid first isolated from the Chinese herb Dichroa febrifuga, but also found in the garden plant Hydrangea. Laboratory synthesis of febrifugine determined that the originally reported stereochemistry was incorrect.

Lobelanine is a chemical precursor in the biosynthesis of lobeline.