| Revision as of 13:15, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 460806978 of page Piperazine for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey'). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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|ImageFileL1 = Piperazine Structural Formula V1.svg |
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| Reference = <ref>'']'', 11th Edition, '''7431'''.</ref> |
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|ImageSizeL1 = 70px |
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| ImageFileL1 = Piperazine structure.svg |
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|ImageFileR1 = Piperazine-3D-balls-B.png |
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| ImageFileR1 = Piperazine-3D-balls-B.png |
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|PIN = Piperazine<ref name=iupac2013>{{cite book |title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) |publisher = ] |date = 2014 |location = Cambridge |page = 142 |doi = 10.1039/9781849733069-FP001 |isbn = 978-0-85404-182-4|chapter = Front Matter }}</ref> |
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| ImageSizeR1 = 120px |
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|SystematicName = 1,4-Diazacyclohexane |
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| IUPACName = piperazine |
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|OtherNames = Hexahydropyrazine<br />Piperazidine<br />Diethylenediamine<br />1,4-Diazinane |
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| SystematicName = |
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|Section1={{Chembox Identifiers |
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| OtherNames = Hexahydropyrazine; Piperazidine; Diethylenediamine |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Section1 = {{Chembox Identifiers |
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|UNII = 1RTM4PAL0V |
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| StdUNII_Ref = {{fdacite|changed|FDA}}= {{fdacite|changed|FDA}}= {{fdacite|correct|FDA}} |
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|ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| UNII = 1RTM4PAL0V |
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|ChEMBL = 1412 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|InChI = 1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 |
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| ChEMBL = <!-- blanked - oldvalue: 1412 --> |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| InChI = 1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 |
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|StdInChIKey = GLUUGHFHXGJENI-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey = <!-- blanked - oldvalue: GLUUGHFHXGJENI-UHFFFAOYSA-N --> |
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|CASNo = 110-85-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| CASNo = 110-85-0 |
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|ChemSpiderID = 13835459 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PubChem = 4837 |
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| ChemSpiderID = 4671 |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| PubChem = 4837 |
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|DrugBank = DB00592 |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| DrugBank = DB00592 |
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|ChEBI = 28568 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| ChEBI = <!-- blanked - oldvalue: 28568 --> |
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|StdInChI = 1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|SMILES = C1CNCCN1 |
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| StdInChI = <!-- blanked - oldvalue: 1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 --> |
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| SMILES = C1CNCCN1 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| ATCCode_prefix = P02 |
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|KEGG = D00807}} |
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|Section2={{Chembox Properties |
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|C=4 |H=10 |N=2 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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|Appearance = White crystalline solid |
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| KEGG = D00807 }} |
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|Density = |
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|MeltingPtC = 106 |
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| C=4 | H=10 | N=2 |
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|MeltingPt_ref = <ref name=Merck>'']'', 11th Edition, '''7431'''</ref> |
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| MolarMass = 86.136 g/mol |
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|BoilingPtC = 146 |
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| Appearance = White crystalline solid |
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|BoilingPt_notes = Sublimates |
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| MeltingPtC = 106 |
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| Melting_notes = <ref name=Merck>'']'', 11th Edition, '''7431'''</ref> |
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|Solubility = Freely soluble<ref name=Merck/> |
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| BoilingPtC = 146 |
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|pKa = 9.8 |
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| Boiling_notes = <ref name=Merck/> |
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|pKb = 4.19<ref name=Merck/> |
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|MagSus = -56.8·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Solubility = Freely soluble<ref name=Merck/> |
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| pKa = 4.19<ref name=Merck/> |
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| NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0 | NFPA-O = |
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|Section6={{Chembox Pharmacology |
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'''Piperazine''' ({{IPAc-en|p|aɪ|ˈ|p|ɛr|ə|z|iː|n}}) is an ] that consists of a six-membered ring containing two ] ] at opposite positions in the ring.<ref>{{Cite web |last=PubChem |title=Piperazine |url=https://pubchem.ncbi.nlm.nih.gov/compound/4837 |access-date=2024-03-08 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> Piperazine exists as small ] ] ]s with a ] taste. |
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The piperazines are a broad class of ]s, many with important pharmacological properties, which contain a core piperazine ].<ref>{{cite book |doi=10.1016/B978-0-12-415816-0.00008-0 |chapter=1-Benzylpiperazine and other Piperazine-based Derivatives |title=Novel Psychoactive Substances |date=2013 |last1=Gee |first1=Paul |last2=Schep |first2=Leo |pages=179–209 |isbn=978-0-12-415816-0 }}</ref> |
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==Origin and naming== |
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Piperazines were originally named because of their chemical similarity with ], part of the structure of ] in the ] plant (''Piper nigrum'').<ref>{{cite book |first=Alexander |last=Senning |title=Elsevier's Dictionary of Chemoetymology |year=2006 |isbn=978-0-444-52239-9 |location=Amsterdam |publisher=Elsevier}}</ref> 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 '']'' ]. |
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==Chemistry== |
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Piperazine is freely soluble in water and ], but insoluble in ]. It is a weak ] with two ] of 5.35 and 9.73 at 25 °C.; the ] of a 10% aqueous solution of piperazine is 10.8–11.8. Piperazine readily absorbs water and ] from the air. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ] with ], by the action of ] and ] on ] ], or by reduction of ] with sodium in ]. |
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A form in which piperazine is commonly available industrially is as the hexa], C<sub>4</sub>H<sub>10</sub>N<sub>2</sub>·6H<sub>2</sub>O, which melts at 44 °C and boils at 125–130 °C.<ref name = MerckI>''The Merck index, 10th Ed.'' (1983), p. 1076, Rahway:Merck & Co.</ref> |
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Two common salts in the form of which piperazine is usually prepared for pharmaceutical or ] purposes are the citrate, 3C<sub>4</sub>H<sub>10</sub>N<sub>2</sub>·2C<sub>6</sub>H<sub>8</sub>O<sub>7</sub> (i.e. containing 3 molecules of piperazine to 2 molecules of ]), and the adipate, C<sub>4</sub>H<sub>10</sub>N<sub>2</sub>·C<sub>6</sub>H<sub>10</sub>O<sub>4</sub> (containing 1 molecule each of piperazine and ]).<ref name = MerckI/> |
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==Industrial production== |
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Piperazine is formed as a co-product in the ammoniation of ] or ]. These are the only routes to the chemical used commercially.<ref>''Ashford's Dictionary of Industrial Chemicals'', 3rd edition, 7332</ref> The piperazine is separated from the product stream, which contains ], ], ] and other related linear and cyclic chemicals of this type. |
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==As an anthelmintic== |
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Piperazine was marketed by Bayer as an ] in the early 20th century, and was featured in print ads alongside other popular Bayer products at the time, including ].<ref>{{Cite web|last=Imgur|title=imgur.com|url=https://imgur.com/a/gVIqE64|access-date=2021-03-04|website=Imgur|language=en}}</ref> In fact, a large number of piperazine compounds have an anthelmintic action. Their mode of action is generally by ] ], which allows the host body to easily expel the invasive organism. The neuromuscular effects are thought to be caused by blocking ] at the myoneural junction. This action is mediated by its ] effects upon the inhibitory ]. Its selectivity for ] is because ] use ] only in the ], and the GABA receptor of helminths is of a different isoform from that of vertebrates.<ref>{{Cite journal|vauthors = Martin RJ|date=31 July 1997|title=Modes of action of anthelmintic drugs|journal=The Veterinary Journal|volume=154 |issue = 1 |doi=10.1016/S1090-0233(05)80005-X|pages=11–34|pmid=9265850 }}</ref> |
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''Piperazine hydrate'', ''piperazine adipate'' and ''piperazine citrate'' (used to treat ] and ]<ref>{{Cite web|url=http://apps.who.int/medicinedocs/en/d/Jh2922e/3.2.4.html|archive-url=https://web.archive.org/web/20100715113324/http://apps.who.int/medicinedocs/en/d/Jh2922e/3.2.4.html|url-status=dead|archive-date=July 15, 2010|title=Helminths: Intestinal nematode infection: Piperazine|date=1995|website=WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition|publisher=]|access-date=2015-08-29}}</ref>) are the most common anthelmintic piperazine compounds. These drugs are often referred to simply as "piperazine" which may cause confusion between the specific anthelmintic drugs, the entire class of piperazine-containing compounds, and the compound itself. |
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], a derivative of piperazine, is used to treat some types of ]. |
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==Other uses== |
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Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials. Piperazines, especially ] and ] were extremely common adulterants in the club and rave scene, often being passed off as ], although they do not share many similarities in their effects. |
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Piperazine is also a fluid used for CO<sub>2</sub> and H<sub>2</sub>S scrubbing in association with ] (MDEA). |
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===Carbon capture and storage=== |
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] |
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Amine blends that are activated by concentrated piperazine are used extensively in commercial CO<sub>2</sub> removal for ] (CCS) because piperazine advantageously allows for protection from significant thermal and oxidative degradation at typical coal ] conditions. The thermal degradation rates for ] (MDEA) and piperazine (PZ) are negligible, and PZ, unlike other metals, protect MDEA from oxidative degradation.<ref>{{cite journal|last1=Closmann|first1=Fred|last2=Nguyen|first2=Thu|last3=Rochelle|first3=Gary T.|title=MDEA/Piperazine as a solvent for CO2 capture|journal=Energy Procedia|date=February 2009|volume=1|issue=1|pages=1351–1357|doi=10.1016/j.egypro.2009.01.177|doi-access=free}}</ref> This increased stability of the MDEA/PZ solvent blend over MDEA and other amine solvents provides for greater capacity for and requires less work to capture a given amount of CO<sub>2</sub>. |
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Piperazine's ] is low, so it is often used in relatively small amounts to supplement another amine solvent. One or more of piperazine's performance advantages are often compromised in practice due to its low concentration; nonetheless, the CO<sub>2</sub> absorption rate, heat of absorption, and solvent capacity are increased through the addition of piperazine to ] solvents, the most common of which is ] due to its unmatched high rate and capacity efficiency. For example, a 5 m PZ/5 m MDEA blend yields an 11% larger difference in CO<sub>2</sub> concentration than 8 m PZ between the lean (inlet absorbent) and rich (outlet absorbent) amine solvent streams, or in other words, more CO<sub>2</sub> is removed from the sour (flue) gas stream per unit mass of solvent, and an almost 100% larger concentration difference than 7 m ].<ref>{{cite journal|last1=Li|first1=Le|last2=Voice|first2=Alexander K.|last3=Li|first3=Han|last4=Namjoshi|first4=Omkar|last5=Nguyen|first5=Thu|last6=Du|first6=Yang|last7=Rochelle|first7=Gary T.|title=Amine blends using concentrated piperazine|journal=Energy Procedia|date=2013|volume=37|pages=353–369|doi=10.1016/j.egypro.2013.05.121|doi-access=free}}</ref> |
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Given that typical amine-based absorption processes run at temperatures from 45 °C to 55 °C, the capabilities of piperazine are well within the bounds of and thus favored for carbon capture. Piperazine can be thermally regenerated through ] and other methods after being used in operating temperatures up to 150 °C and recycled back into the absorption process, providing for higher overall energy performance in amine gas treating processes.<ref name="rochelle2011">{{cite journal|last1=Rochelle|first1=Gary|last2=Chen|first2=Eric|last3=Freeman|first3=Stephanie|last4=Wagener|first4=David V.|last5=Xu|first5=Qing|last6=Voice|first6=Alexander|title=Aqueous piperazine as the new standard for CO2 capture technology|journal=Chemical Engineering Journal|date=15 July 2011|volume=171|issue=3|pages=725–733|doi=10.1016/j.cej.2011.02.011}}</ref> |
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The advantages to using concentrated piperazine (CPZ) as an additive had been confirmed through, for example, three pilot plants in Australia that are operated by ]. This program was launched to explore remedies to the high costs of post-combustion carbon capture, and the results were positive. Using CPZ, which is more reactive and thermally stable than standard MEA solutions, capital and compression (energy) costs were lowered through size reductions in absorber columns and solvent regeneration at higher temperatures.<ref>{{Cite report |last1=Cottrell|first1=Aaron|last2=Cousins|first2=Ashleigh|last3=Huang|first3=Sanger|last4=Dave|first4=Narendra|last5=Do|first5=Thong|last6=Feron|first6=Paul H.M.|last7=McHugh|first7=Stephen|last8=Sinclair|first8=Michael|date= September 2013|title= Concentrated Piperazine based Post-Combustion Capture for Australian coal-fired power plants|url=https://www.globalccsinstitute.com/publications/concentrated-piperazine-based-post-combustion-capture-australian-coal-fired-power|publisher= Australian National Low Emissions Coal Research & Development|pages= 9–31|access-date=3 May 2016}}</ref> |
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====Chemistry==== |
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The amine groups on piperazine react readily with carbon dioxide to produce PZ carbamate at a low loading (mol CO<sub>2</sub>/equiv PZ) range and PZ bicarbamate at an operating range of 0.31-0.41 mol CO<sub>2</sub>/equiv PZ, enhancing the rate of overall CO<sub>2</sub> absorbed under operating conditions (refer to Figure 1 below). Due to these reactions, there is limited free piperazine present in the solvent, resulting in its low volatility and rates of precipitation as PZ-6H<sub>2</sub>O.<ref name="rochelle2011"/> |
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==Piperazine derivatives as drugs== |
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{{See also|Substituted piperazine}} |
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Many currently notable drugs contain a piperazine ring as part of their molecular structure. They may be used as antiparasitic drugs.<ref>{{cite book |doi=10.1016/b978-070202858-8.50012-9 |chapter=Antiparasitic drugs |title=Small Animal Clinical Pharmacology |date=2008 |last1=Page |first1=Stephen W. |pages=198–260 |isbn=978-0-7020-2858-8 }}</ref> Other examples include:<ref>{{Cite web |last=PubChem |title=Piperazine |url=https://pubchem.ncbi.nlm.nih.gov/compound/4837 |access-date=2023-05-03 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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* ] (2C-B-BZP) |
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* ] (DCPP) |
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* ] (DBZP) |
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'''Others''' |
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* Piperazine (itself) |
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* ] (antineoplastic agent) |
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Most of these agents can be classified as either ]s, ]s, ]s (benzhydrylpiperazines), ]s, ]s, or ]s (with the piperazine ] attached to the ] ] via a ]). |
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==See also== |
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==References== |
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{{reflist}} |
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==External links== |
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{{EB1911 poster|Piperazin}} |
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* {{Cite web|url=http://www.chemicalland21.com/lifescience/UH/PIPERAZINE%20CITRATE.htm|title=PIPERAZINE CITRATE|website=Сhemicalland21.com|access-date=2015-08-29}} |
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{{Piperazines}} |
|
|
{{Adrenergics}} |
|
|
{{Dopaminergics}} |
|
|
{{Serotonergics}} |
|
|
{{Antihistamines}} |
|
|
{{Anthelmintics}} |
|
|
{{antipsychotics}} |
|
|
{{Hallucinogens}} |
|
|
{{stimulants}} |
|
|
|
|
|
{{Authority control}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |