View source for Piperazine

{{chembox
| verifiedrevid = 310487340
| Reference = <ref>''[[Merck Index]]'', 11th Edition, '''7431'''.</ref>
| ImageFileL1 = Piperazine structure.svg
| ImageSizeL1 = 70px
| ImageFileR1 = Piperazine-3D-balls-B.png
| ImageSizeR1 = 120px
| IUPACName = piperazine
| SystematicName = 
| OtherNames = Hexahydropyrazine<br>Piperazidine<br>Diethylenediamine
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite}}
| CASNo = 110-85-0
| ChemSpiderID = 13855459
| PubChem = 4837
| SMILES = C1CNCCN1
| ATCCode_prefix = P02
| ATCCode_suffix = CB01
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = | C=4 | H=10 | N=2
| MolarMass = 86.136 g/mol
| Appearance = 
| Density = 
| MeltingPt = 106°C
| Melting_notes = 
| BoilingPt = 146°C
| Boiling_notes = 
| pKa = 5.68, 9.82
| pKb = }}
| Section5 = {{Chembox Pharmacology
| AdminRoutes = 
| Bioavail = 
| Metabolism = 
| HalfLife = 
| ProteinBound = 60-70%
| Excretion = 
| Legal_status = 
| Legal_US = 
| Legal_UK = 
| Legal_AU = 
| Legal_CA = 
| PregCat = 
| PregCat_AU = 
| PregCat_US = }}
| Section7 = {{Chembox Hazards
|   NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0 | NFPA-O = 
}}
}}

'''Piperazine''' is an [[organic compound]] that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small [[alkaline]] [[deliquescent]] [[crystal]]s with a [[salt|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]], a constituent of [[piperine]] in the [[black pepper]] plant (''Piper nigrum''). 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 (chemistry)|base]] with a [[pKb|pK<sub>b</sub>]] of 4.19; the [[pH]] of a 10% aqueous solution is 10.8-11.8.  Piperazine readily absorbs water and [[carbon dioxide]] from the air.  Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic [[ammonia]] with [[1,2-Dichloroethane|1,2-dichloroethane]], by the action of [[sodium]] and [[ethylene glycol]] on [[ethylene diamine]] [[hydrochloride]], or by reduction of [[pyrazine]] with sodium in [[ethanol]].

== Indications ==

{{Empty section|date=July 2010}}
== As an anthelmintic ==

Piperazine was first introduced as an [[anthelmintic]] in 1953. A large number of piperazine compounds have anthelmintic action. Their mode of action is generally by [[paralysis|paralysing]] parasites, which allows the host body to easily remove or expel the invading organism. This action is mediated by its [[agonist]] effects upon the inhibitory [[GABA]] (γ-aminobutyric acid) receptor. Its selectivity for [[helminths]] is because vertebrates only use GABA in the [[CNS]] and the helminths' GABA receptor is a different isoform to the vertebrate's one. ''Piperazine hydrate'' and ''piperazine citrate'' are the main anthelminthic piperazines. These drugs are often referred to simply as "piperazine" which may cause confusion between the specific anthelmintic drugs and the entire class of piperazine-containing compounds.

== Other uses ==

Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials.  Piperazines, especially [[Benzylpiperazine|BZP]] and [[Trifluoromethylphenylpiperazine|TFMPP]] have become un-popular substitutes in the club scene for [[MDMA]] (due to their similarity in effect to amphetamines like MDMA).

Piperazine is also a fluid used for CO<sub>2</sub> and H<sub>2</sub>S scrubbing in association with [[methyl diethanolamine]] (MDEA).

== Piperazine derivatives as drugs ==

Piperazine was introduced to [[medicine]] as a solvent for [[uric acid]]. When taken into the body the drug is partly [[redox|oxidized]] and partly eliminated unchanged. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble [[urate]], but in clinical experience it has not proved equally successful. [[Lycetol]], [[lysidine]] and [[sidonal]] are compounds having similar action. Many piperazine derivatives are notable successful drugs, including:

<div style="-moz-column-count:2; column-count:2; -webkit-column-count:2;">

; [[Antianginal]]s
* [[Ranolazine]]
* [[Trimetazidine]]

; [[Antidepressant]]s
* [[Alnespirone]]
* [[Amoxapine]]
* [[Befuraline]]
* [[Binospirone]]
* [[Buspirone]]
* [[Flesinoxan]]
* [[Gepirone]]
* [[Ipsapirone]]
* [[Nefazodone]]
* [[Piberaline]]
* [[Tandospirone]]
* [[Trazodone]]
* [[Vilazodone]]
* [[Zalospirone]]

; [[Antihistamine]]s
* [[Buclizine]]
* [[Cetirizine]]
* [[Cinnarizine]]
* [[Cyclizine]]
* [[Hydroxyzine]]
* [[Levocetirizine]]
* [[Meclizine]]
* [[Niaprazine]]

; [[Antipsychotic]]s
* [[Typical antipsychotic|Typical]]
** [[Flupentixol]]
** [[Fluphenazine]]
** [[Perphenazine]]
** [[Prochlorperazine]]
** [[Thiothixene]]
** [[Trifluoperazine]]
** [[Zuclopenthixol]]
* [[Atypical antipsychotic|Atypical]]
** [[Amperozide]]
** [[Aripiprazole]]
** [[Clozapine]]
** [[Lurasidone]]
** [[Olanzapine]]
** [[Perospirone]]
** [[Ziprasidone]]

; [[Recreational drug use|Recreational Drug]]s
* [[4-Bromo-2,5-dimethoxy-1-benzylpiperazine]] (2C-B-BZP)
* [[1-Benzylpiperazine]] (BZP)
* [[2,3-Dichlorophenylpiperazine]] (DCPP)
* [[1,4-Dibenzylpiperazine]] (DBZP)
* [[4-Methyl-1-benzylpiperazine]] (MBZP)
* [[3-Chlorophenylpiperazine]] (mCPP)
* [[3,4-Methylenedioxy-1-benzylpiperazine]] (MDBZP)
* [[4-Methoxyphenylpiperazine]] (MeOPP)
* [[4-Chlorophenylpiperazine]] (pCPP)
* [[4-Fluorophenylpiperazine]] (pFPP)
* [[3-Trifluoromethylphenylpiperazine]] (TFMPP)

; [[Urological]]s
* [[Sildenafil]]
* [[Vardenafil]]

; Others
* [[6-Nitroquipazine]]
* [[Antrafenine]]
* [[Fipexide]]
* [[Imatinib]]
* Piperazine (itself)
* [[Quipazine]]

</div>

Most of these agents can be classified as either [[phenylpiperazine]]s, [[benzylpiperazine]]s, [[diphenylmethylpiperazine]]s (benzhydrylpiperazines), [[pyridinylpiperazine]]s, [[pyrimidinylpiperazine]]s, or [[tricyclic]]s (with the piperazine [[functional group|ring]] attached to the [[heterocyclic]] [[functional group|moiety]] via a [[side chain]]).

== See also ==
* [[Pyridine]]
* [[Piperidine]]

== References ==
{{Reflist|2}}
* {{Wikisource1911Enc Citation|Piperazin}}

== External links ==
* [http://www.erowid.org/chemicals/piperazines/piperazines.shtml Erowid piperazine vault]
* [http://www.tripme.co.nz Piperazine Reviews and Information]

{{Anthelmintics}}
{{Piperazines}}

[[Category:Amines]]
[[Category:Piperazines|*]]

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