Piperazine

Piperazine
Names
	Preferred IUPAC name Piperazine
	Systematic IUPAC name 1,4-Diazacyclohexane
	Other names Hexahydropyrazine; Piperazidine; Diethylenediamine; 1,4-Diazinane
Identifiers
CAS Number	110-85-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28568 ;
ChEMBL	ChEMBL1412 ;
ChemSpider	13835459 ;
DrugBank	DB00592 ;
ECHA InfoCard	100.003.463
KEGG	D00807 ;
PubChem CID	4837;
UNII	1RTM4PAL0V ;
CompTox Dashboard (EPA)	DTXSID1021164 ;
	InChI InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 Key: GLUUGHFHXGJENI-UHFFFAOYSA-N ; InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2;
	SMILES C1CNCCN1;
Properties
Chemical formula	C4H10N2
Molar mass	86.138 g·mol−1
Appearance	White crystalline solid
Melting point	106 °C (223 °F; 379 K)
Boiling point	146 °C (295 °F; 419 K) Sublimes
Solubility in water	Freely soluble
Acidity (pKa)	9.8
Basicity (pKb)	4.19
Magnetic susceptibility (χ)	−56.8·10−6 cm3/mol
Pharmacology
ATC code	P02CB01 (WHO)
	Pharmacokinetics:
Protein binding	60-70%
Hazards
NFPA 704 (fire diamond)	2 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Piperazine (/paɪˈpɛrəziːn/) is an organic compound with the formula (CH₂CH₂NH)₂. In term of its structure, it can be described as cyclohexane with the 1- and 4-CH₂ groups replaced by NH.^[3] Piperazine exists as deliquescent solid with a saline taste. Piperazine is freely soluble in water and ethylene glycol, but poorly soluble in diethyl ether. Piperazine is commonly available industrially is as the hexahydrate, (CH₂CH₂NH)₂·6H₂O, which melts at 44 °C and boils at 125–130 °C.^[4]

Substituted derivatives of piperazine are a broad class of chemical compounds. Many piperazines have useful pharmacological properties, prominent examples include viagra, ciprofloxacin, and ziprasidone.^[5]^[6]

^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 142. doi:10.1039/9781849733069-FP001. 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.
^ The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co.
^ Grygorenko, Oleksandr O.; Radchenko, Dmytro S.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A.; Komarov, Igor V. (2011). "Bicyclic Conformationally Restricted Diamines". Chemical Reviews. 111 (9): 5506–5568. doi:10.1021/cr100352k. PMID 21711015.
^ Gee, Paul; Schep, Leo (2013). "1-Benzylpiperazine and other Piperazine-based Derivatives". Novel Psychoactive Substances. pp. 179–209. doi:10.1016/B978-0-12-415816-0.00008-0. ISBN 978-0-12-415816-0.

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 142. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[Merck-2] Merck Index, 11th Edition, 7431

[3] PubChem. "Piperazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-03-08.

[MerckI-4] The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co.

[5] Grygorenko, Oleksandr O.; Radchenko, Dmytro S.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A.; Komarov, Igor V. (2011). "Bicyclic Conformationally Restricted Diamines". Chemical Reviews. 111 (9): 5506–5568. doi:10.1021/cr100352k. PMID 21711015.

[6] Gee, Paul; Schep, Leo (2013). "1-Benzylpiperazine and other Piperazine-based Derivatives". Novel Psychoactive Substances. pp. 179–209. doi:10.1016/B978-0-12-415816-0.00008-0. ISBN 978-0-12-415816-0.

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