Piperidine
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| Piperidine | |
|---|---|
| Image:Piperidine.svg | |
| IUPAC name | Piperidine |
| Other names | Hexahydropyridine Azacyclohexane, pentamethyleneamine |
| Identifiers | |
| CAS number | |
| 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 |
|
| 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.
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.
Contents |
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
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
