Piperazine
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Names | |||
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Preferred IUPAC name
Piperazine[1] | |||
Systematic IUPAC name
1,4-Diazacyclohexane | |||
Other names
Hexahydropyrazine
Piperazidine Diethylenediamine 1,4-Diazinane | |||
Identifiers | |||
3D model (
JSmol ) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.003.463 | ||
KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C4H10N2 | |||
Molar mass | 86.138 g·mol−1 | ||
Appearance | White crystalline solid | ||
Melting point | 106 °C (223 °F; 379 K)[2] | ||
Boiling point | 146 °C (295 °F; 419 K)[2] Sublimates | ||
Freely soluble[2] | |||
Acidity (pKa) | 9.8 | ||
Basicity (pKb) | 4.19[2] | ||
-56.8·10−6 cm3/mol | |||
Pharmacology | |||
P02CB01 (WHO) | |||
Pharmacokinetics: | |||
60-70% | |||
Hazards | |||
NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Piperazine ( taste.
The piperazines are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group.[4]
Origin and naming
Piperazines were originally named because of their chemical similarity with
Chemistry
Piperazine is freely soluble in water and
.A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44 °C and boils at 125–130 °C.[6]
Two common salts in the form of which piperazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2.2C6H8O7 (i.e. containing 3 molecules of piperazine to 2 molecules of citric acid), and the adipate, C4H10N2.C6H10O4 (containing 1 molecule each of piperazine and adipic acid).[6]
Industrial production
Piperazine is formed as a co-product in the ammoniation of
As an anthelmintic
Piperazine was marketed by Bayer as an
Piperazine hydrate, piperazine adipate and piperazine citrate (used to treat
Diethylcarbamazine, a derivative of piperazine, is used to treat some types of filariasis.
Other uses
Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials. Piperazines, especially BZP and TFMPP were extremely common adulterants in the club and rave scene, often being passed off as MDMA, although they do not share many similarities in their effects.
Piperazine is also a fluid used for CO2 and H2S scrubbing in association with
Carbon capture and storage
Amine blends that are activated by concentrated piperazine are used extensively in commercial CO2 removal for
Piperazine's
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 multi-stage flash distillation 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.[13]
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
Chemistry
The amine groups on piperazine react readily with carbon dioxide to produce PZ carbamate at a low loading (mol CO2/equiv PZ) range and PZ bicarbamate at an operating range of 0.31-0.41 mol CO2/equiv PZ, enhancing the rate of overall CO2 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-6H2O.[13]
Piperazine derivatives as drugs
Many currently notable drugs contain a piperazine ring as part of their molecular structure. They may be used as antiparasitic drugs.[15] Other examples include:[16]
- 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)
- Methoxypiperamide (MeOP or MEXP)
- 4-Chlorophenylpiperazine(pCPP)
- 4-Fluorophenylpiperazine(pFPP)
- 3-Trifluoromethylphenylpiperazine(TFMPP)
Others
- 6-Nitroquipazine
- Antrafenine
- Diethylcarbamazine
- Diphenazin
- Fipexide
- Imatinib
- NSI-189
- Piperazine (itself)
- Pipobroman (antineoplastic agent)
- Quipazine
- Sunifiram (nootropic)
- Tolpiprazole (tranquilizer)
Most of these agents can be classified as either
See also
- Amine gas treating
- Methyl diethanolamine
- Piperidine
- Pyrazine
- Pyridine
References
- ISBN 978-0-85404-182-4.
- ^ a b c d Merck Index, 11th Edition, 7431
- ^ PubChem. "Piperazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-03-08.
- ^ "Piperazine - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2023-05-03.
- ISBN 978-0-444-52239-9.
- ^ a b The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co.
- ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 7332
- ^ Imgur. "imgur.com". Imgur. Retrieved 2021-03-04.
- PMID 9265850.
- WHO. 1995. Archived from the originalon July 15, 2010. Retrieved 2015-08-29.
- .
- .
- ^ .
- ^ Cottrell, Aaron; Cousins, Ashleigh; Huang, Sanger; Dave, Narendra; Do, Thong; Feron, Paul H.M.; McHugh, Stephen; Sinclair, Michael (September 2013). Concentrated Piperazine based Post-Combustion Capture for Australian coal-fired power plants (Report). Australian National Low Emissions Coal Research & Development. pp. 9–31. Retrieved 3 May 2016.
- ISBN 978-0-7020-2858-8, retrieved 2023-05-03
- ^ PubChem. "Piperazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-05-03.
External links
- "PIPERAZINE CITRATE". Сhemicalland21.com. Retrieved 2015-08-29.