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Encyclopedia > Piperidine
Piperidine
IUPAC name Piperidine
Other names Hexahydropyridine
Azacyclohexane, pentamethyleneamine
Identifiers
CAS number 110-89-4
RTECS number TM3500000
SMILES C1CCCCN1
Properties
Molecular formula C5H11N
Molar mass 85.15 g/mol
Appearance colourless liquid
Density 0.862 g/ml, liquid
Melting point

−7 °C Image File history File links This is a lossless scalable vector image. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... This article does not cite any references or sources. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

Boiling point

106 °C Italic text This article is about the boiling point of liquids. ...

Solubility in water miscible
Acidity (pKa) 11.24
Viscosity  ? cP at ? °C
Hazards
EU classification Flammable (F)
Toxic (T)
NFPA 704

Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ...

3
3
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R-phrases R11, R23/24, R34
Related Compounds
Related compounds pyridine
pyrrolidine
piperazine
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Piperidine is an organic compound with the molecular formula C5H11N. It is a heterocyclic amine with a six-membered ring containing five carbon atoms and one nitrogen atom. It is a clear liquid with a pepper-like odor. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... Flash point 3 °C R/S statement R: 11 20/21/22 35 S: 16 26 28 36/37 45 RTECS number UX9650000 Related compounds Related compounds pyrrole piperidine Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and... Basic piperazine structure Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image). ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Pyridine a simple heterocyclic compound Heterocyclic compounds are organic compounds which contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... For other uses, see Carbon (disambiguation). ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...


The piperidine structural motif is present in numerous natural alkaloids such as piperine and quinine, and is the main active chemical agent in black pepper and relatives (Piper sp.), hence the name. Piperidine is also a structural element of many pharmaceutical drugs such as raloxifene, minoxidil, thioridazine and mesoridazine. Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Categories: Stub ... Quinine (IPA: ) is a natural white crystalline alkaloid having antipyretic (fever-reducing), antimalarial, analgesic (painkilling), and anti-inflammatory properties and a bitter taste. ... Binomial name L. Black pepper (Piper nigrum) is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. ... Species See text. ... Raloxifene is an oral selective estrogen receptor modulator which is used in the prevention of osteoporosis in postmenopausal women. ... Minoxidil is a vasodilator and originally was exclusively used as an oral drug (Loniten®) to treat high blood pressure. ... Thioridazine is a piperidine antipsychotic drug previously widely used in the treatment of schizophrenia and psychosis. ... Serentil® (mesoridazine besylate) is a neuroleptic drug that is used in the treatment of schizophrenia, organic brain disorders, psychoneuroses, and alcoholism. ...


Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1] due to its use (peaking in the 1970s) in the clandestine manufacture of PCP. It is also a byproduct of burning phencyclidine (PCP, phenylcyclohexylpiperidine). United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances Opened for signature December 20, 1988[1] at Vienna Entered into force November 11, 1990[2] Conditions for entry into force 20 ratifications Parties 170[3] The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and... The 1970s decade refers to the years from 1970 to 1979, also called The Seventies. ... “Angel Dust” redirects here. ...


Piperidine is often used as a solvent for its mild basic properties, most notably in Fmoc-strategy solid phase peptide synthesis. The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... It has been suggested that this article or section be merged into peptide synthesis. ...


The major industrial application of piperidine is for the production of dipiperidinyl dithium tetrasulfide, which is used as a rubber vulcanization accelerator. Vulcanization refers to a specific curing process of rubber involving high heat and the addition of sulfur. ...


Piperidine is naturally found in fire ant venom, and is the cause of the burning sensation associated with the bite of these insects. Species More than 280 species and subspecies, see text For the species of fire ant common to the Southern U.S., see Red imported fire ant Fire ants, sometimes referred to as simply red ants, are stinging ants of which there are over 280 species worldwide. ...


Piperidine is also commonly used in chemical degradation reactions, such as the DNA sequencing method invented by Walter Gilbert in 1977, for cleavage of particular modified nucleotides. Piperidine is also commonly used as a strong base for the deprotection of amino acids in solid-phase peptide synthesis. It has been suggested that solid phase peptide synthesis be merged into this article or section. ...

Contents

Use in pharmaceutical drugs

Many pharmaceutical drugs contain a piperidine ring because the group tends to impart drug-like physical properties such as water solubility and bioavailability. Examples of drugs that contain piperidines include mesoridazine, thioridazine, haloperidol, droperidol, PCP, benperidol, and risperidone. In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Serentil® (mesoridazine besylate) is a neuroleptic drug that is used in the treatment of schizophrenia, organic brain disorders, psychoneuroses, and alcoholism. ... Thioridazine is a piperidine antipsychotic drug previously widely used in the treatment of schizophrenia and psychosis. ... Haloperidol (sold under the tradenames Aloperidin, Bioperidolo, Brotopon, Dozic, Duraperidol (Germany), Einalon S, Eukystol, Haldol, Halosten, Keselan, Linton, Peluces, Serenace, Serenase, Sigaperidol) is a conventional, or typical, butyrophenone antipsychotic drug. ... Droperidol (Dropletan®, Dridol® or Inapsine®) is an antidopaminergic drug used as an antiemetic and antipsychotic. ... PCP may refer to: In politics: Partido Comunista del Peru, also known as Shining Path Partido Comunista Paraguayo, Paraguayan Communist Party Partido Comunista Peruano, Peruvian Communist Party Partido Comunista Português, Portuguese Communist Party Partido Comunista Puertorriqueño, Puerto Rican Communist Party Partit Català Proletari, Proletarian Catalan Party In science... Benperidol is a drug which is a butyrophenone derivative. ... Risperdal tablets Risperidone (pronounced Ris-PER-ǐ-dōn and sold under the trade name Risperdal in the United States, Canada, the United Kingdom and several other countries, Risperdal or Ridal in New Zealand, Rispolept in Eastern Europe, and Belivon, or Rispen elsewhere) is an atypical antipsychotic medication developed by Janssen...


See also

Basic piperazine structure Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image). ...

References

External links

  • International Chemical Safety Card 0317

 
 

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