Piperidine
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Piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name ''Piper (genus), Piper'', which is the Latin word for Black pepper, pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring Solenopsin, solenopsins. Production Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson (chemist), Thomas Anderson and again, independently, in 1852 by the French chemist Auguste André Thomas Cahours, Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Industrially, piperidine is produced by the hydrogenation o ...
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Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ...
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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 the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings. Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers. Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom. Total ...
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Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ...
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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 the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings. Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers. Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom. Total ...
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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 needles ( ...
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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 , , Medicinal plant, plants, an ...
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Amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. A ...
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Piperazine
Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group. Origin and naming Piperazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (''Piper nigrum''). The -az- infix added to "piperazine" refers to the extra nitrogen atom, compared to piperidine. It is important to note, however, that piperazines are ''not'' derived from plants in the '' Piper'' genus. Chemistry Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with two pKb of 5.35 and 9.73 at 25 °C.; the pH of a 10% aqueous solution of piperazine is 10.8–11.8. Pi ...
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Fire Ant
Fire ants are several species of ants in the genus ''Solenopsis'', which includes over 200 species. ''Solenopsis'' are stinging ants, and most of their common names reflect this, for example, ginger ants and tropical fire ants. Many of the names shared by this genus are often used interchangeably to refer to other species of ant, such as the term red ant, mostly because of their similar coloration despite not being in the genus Solenopsis. Both ''Myrmica rubra ''Myrmica rubra'', also known as the common red ant or erroneously the European fire ant, is a species of ant of the genus '' Myrmica'', found all over Europe and is now invasive in some parts of North America and Asia. It is mainly red in colou ...'' and ''Pogonomyrmex barbatus'' are common examples of non-Solenopsis ants being termed red ants. None of these names apply to all species of ''Solenopsis'' nor only to ''Solenopsis'' species; for example the colloquial names for several species of weaver ants in the genus ...
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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 San ...
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Anabasine
Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (''Nicotiana glauca'') plant, a close relative of the common tobacco plant (''Nicotiana tabacum''). It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide. 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 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. In larger amounts it is thought to be teratogenic in swine. The intravenous LD50 of anabasine ranges from 11 mg/kg to 16 mg/kg in mice, depending on the enantiomer. Analogs B. Bhatti, et al. made some higher potency sterically strained bicyclic analogs of anabasine: *2-(Pyridin-3-yl)-1-azabicyclo .2. ...
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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 the ch ...
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