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Chavicine
Chavicine is an alkaloid found in black pepper and other species of the genus ''Piper''. It is one of the four geometric isomers of piperine Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine. Preparation Due to its poor solubility in water, piperine is typi .... See also * Guineesine References {{Chem-stub Benzodioxoles Piperidine alkaloids Carboxamides Alkene derivatives ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , ,

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Black Pepper
Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit, known as a peppercorn, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in diameter (fresh and fully mature), dark red, and contains a stone which encloses a single pepper seed. Peppercorns and the ground pepper derived from them may be described simply as ''pepper'', or more precisely as ''black pepper'' (cooked and dried unripe fruit), ''green pepper'' (dried unripe fruit), or ''white pepper'' (ripe fruit seeds). Black pepper is native to the Malabar Coast of India, and the Malabar pepper is extensively cultivated there and in other tropical regions. Ground, dried, and cooked peppercorns have been used since antiquity, both for flavour and as a traditional medicine. Black pepper is the world's most traded spice, and is one of the most common spices added to cuisines around the world. Its spiciness is due to t ...
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Piper (genus)
''Piper'', the pepper plants or pepper vines, is an economically and ecologically important genus in the family Piperaceae. It contains about 1,000-2,000 species of shrubs, herbs, and lianas, many of which are dominant species in their native habitat. The diversification of this taxon is of interest to understanding the evolution of plants. Pepper plants belong to the magnoliids, which are angiosperms but neither monocots nor eudicots. Their family, Piperaceae, is most closely related to the lizardtail family ( Saururaceae), which in fact generally look like smaller, more delicate and amphibious pepper plants. Both families have characteristic tail-shaped inflorescences covered in tiny flowers. A somewhat less close relative is the pipevine family (Aristolochiaceae). A well-known and very close relative – being also part of the Piperaceae – are the radiator plants of the genus '' Peperomia''. The scientific name ''Piper'' and the common name "pepper" are derived from the ...
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Geometric Isomer
Geometry (; ) is, with arithmetic, one of the oldest branches of mathematics. It is concerned with properties of space such as the distance, shape, size, and relative position of figures. A mathematician who works in the field of geometry is called a ''geometer''. Until the 19th century, geometry was almost exclusively devoted to Euclidean geometry, which includes the notions of point, line, plane, distance, angle, surface, and curve, as fundamental concepts. During the 19th century several discoveries enlarged dramatically the scope of geometry. One of the oldest such discoveries is Carl Friedrich Gauss' ("remarkable theorem") that asserts roughly that the Gaussian curvature of a surface is independent from any specific embedding in a Euclidean space. This implies that surfaces can be studied ''intrinsically'', that is, as stand-alone spaces, and has been expanded into the theory of manifolds and Riemannian geometry. Later in the 19th century, it appeared that geometri ...
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Piperine
Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine. Preparation Due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane. The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers. Piperine can also be prepared by treating a concentrated alcoholic extract of black pepper with an alcoholic solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine). The solution is decanted from the insoluble residue and left to stand overnight. During this period, the alkaloid slowly crystallizes from the solution. Piperine has been synthesized by the action of piperonoyl chloride on piperidine. Reactions Piperine forms salts only with strong acids. The platinichloride B4·H2PtCl6 forms orange-red needle ...
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Guineesine
Guineesine (or guineensine) is an alkaloid isolated from long pepper (''Piper longum'') and black pepper (''Piper nigrum''). Research Guineensine inhibits the cellular reuptake of anandamide and 2-arachidonoylglycerol in a mouse model ( EC50 = 290 nM). This causes an increase in the activity of the two neurotransmitters which are classified as endogenous cannabinoids. Guineesine can dose-dependently produce cannabimimetic effects in a mouse model which are indicated by potent catatonic, analgesic, hypo-locomotive and hypo-thermic effects. In addition, the analgesic and catatonic effects were reversed by the cannabinoid receptor type 1 (CB1) inverse agonist rimonabant. Guineesine is also a monoamine oxidase inhibitor (MAOI) ''in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studi ...
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Piperidine Alkaloids
Piperidine alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from piperidine. Alkaloids with a piperidine building block are widespread and are usually further subdivided according to their occurrence and biogenetic origin. The most important representative of piperidine alkaloids is piperine, which is responsible for the pungent taste of pepper. The piperidine alkaloids also include the sedum alkaloids (e.g. sedamine), pelletierine, the lobelia alkaloids (e.g. lobeline), the conium alkaloids (such as coniine) and the pinus alkaloids. Piperin.svg, Piperine Lobeline Structural Formula V2.svg, Lobeline (S)-Coniine Structural Formula V.1.svg, (''S'')-Coniine (2R,8R)-Sedamine Structural Formula V4.svg, Sedamin Solenopsin Structural Formula V.1.svg, Solenopsin 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 ...
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