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Piperidine



Piperidine
IUPAC name Piperidine
Other names Hexahydropyridine
Azacyclohexane, pentamethyleneamine
Identifiers
CAS number 110-89-4
RTECS number TM3500000
SMILES C1CCCCN1
InChI InChI=1/C5H11N/c1-2-
4-6-5-3-1/h6H,1-5H2
Properties
Molecular formula C5H11N
Molar mass 85.15 g/mol
Appearance colourless liquid
Density 0.862 g/ml, liquid
Melting point

−7 °C

Boiling point

106 °C

Solubility in water miscible
Acidity (pKa) 11.24
Viscosity  ? cP at ? °C
Hazards
EU classification Flammable (F)
Toxic (T)
NFPA 704
3
3
3
 
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.

Additional recommended knowledge

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.

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 (also known as angel dust).

Piperidine is often used as a solvent for its mild basic properties, most notably in Fmoc-strategy solid phase peptide synthesis.

The major industrial application of piperidine is for the production of dipiperidinyl dithium tetrasulfide, which is used as a rubber vulcanization accelerator.

Piperidine is naturally found in fire ant venom, and is the cause of the burning sensation associated with the bite of these insects.

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.

Use in pharmaceutical drugs

Many pharmaceutical drugs contain a piperidine ring because the group tends to impart pharmacokinetics such as water solubility and bioavailability. Examples of drugs that contain piperidines include mesoridazine, thioridazine, haloperidol, droperidol, PCP, benperidol, and risperidone.

Most piperidines induce the liver enzyme CYP2D6, resulting in faster metabolism of e.g. many beta-blockers and antiarrhythmics.

See also

References

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Piperidine". A list of authors is available in Wikipedia.
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