Pyridine and piperidine alkaloids

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Alkaloids, e.g. piperine, coniine, trigonelline, pilocarpine, nicotine and sparteine, possess a pyridine or modified pyridine heterocyclic ring system (e.g. piperidine ring).

Piperine Piperine, molecular formula Ci7H19NO3, a component of black pepper (Piper nigrum), has been used in various traditional medicine preparations, and also as an insecticide. Piperine has various effects on human drug metabolizing enzymes, and is marketed under the brand name, Bioperine®, as an adjunct for increasing bioavailability of various dietary supplements, especially curcumin, one of the active ingredients of turmeric (Curcuma longa).

Pyrrolidine system

Piperine ^^ O Coniine

Pyrrolidine system

Pyridine system

Nicotine

Pyridine system

Piperine ^^ O Coniine

Nicotine

Coniine Coniine or (S)-2-propylpiperidine, molecular formula C8H17N, is a poisonous alkaloid found in the hemlock poison and the 'yellow pitcher plant' (Sarracenia flava). Coniine contributes to the foul smell of hemlock. It is a neurotoxin, causes respiratory paralysis and is toxic to all classes of livestock and humans. In 399 BC, Socrates was put to death by this poison.

Nicotine Nicotine, molecular formula C10H14N2, is the major pharmacologically active component of tobacco, Nicotiana tabacum, and is also found extensively in other species of the family Solanaceae, e.g. tomato, potato, aubergine and green pepper. Nicotine is a hygroscopic oily liquid, and miscible with water in its base as well as its salt form. Nicotine possesses two nitrogenous ring systems: one is pyridine, but the other is a pyrrolidine ring system. Thus, this alkaloid can be classified either under pyridine or pyrrolidine.

Nicotine is a potent nerve poison, and is included in many insecticide preparations. In lower concentrations, nicotine is a stimulant, i.e. it increases activity, alertness and memory, and this is one of the main factors that contribute to the dependence-forming properties of tobacco smoking. Nicotine increases heart-rate and blood pressure, and reduces appetite. In higher doses, nicotine acts as a depressant. In large doses, it can cause nausea and vomiting. The main symptoms of the withdrawal of nicotine intake include irritability, headaches, anxiety, cognitive disturbances and sleep disruption.

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The Smoker's Sanctuary

The Smoker's Sanctuary

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