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Piperazine
Systematic (IUPAC) name
piperazine
Identifiers
CAS number	110-85-0
ATC code	P02CB01
PubChem	4837
DrugBank	APRD00225
Chemical data
Formula	C4H10N2
Mol. mass	86.1357 g/mol
SMILES	search in eMolecules, PubChem
Synonyms	Hexahydropyrazine Piperazidine Diethylenediamine
Physical data
Melt. point	106 °C (223 °F)
Boiling point	146 °C (295 °F)
Pharmacokinetic data
Bioavailability	?
Protein binding	60-70%
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

The piperazines are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group.

Contents 1 Origin and naming 2 Chemistry 3 Medicinal Use 4 As an anthelmintic 5 Other uses 6 References 7 See Also 8 External links

Piperazines were originally named because of their chemical similarity with piperidine, a constituent of piperine in the black pepper plant (Piper nigrum).

Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a strong base with a pK_b 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; by the action of sodium and ethylene glycol on ethylene diamine hydrochloride; or by reduction of pyrazine with sodium in ethanol.

Piperazine was originally introduced into medicine as a solvent for uric acid. When taken into the body the drug is partly 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:

• Piperazine citrate (antiparasitic)
• Viagra (impotence drug)
• Levitra (impotence drug)
• Imatinib (leukemia drug)
• Meclizine (motion sickness drug)
• Cyclizine (antiemetic antihistamine)
• Niaprazine (sedating antihistamine)
• Trazodone (sedating antidepressant)
• Nefazodone (analgesic antidepressant)
• Antrafenine (analgesic)
• Befuraline (stimulant antidepressant)
• Trelibet (stimulant antidepressant)
• Fipexide (nootropic)
• Trimetazidine (anti-angina drug)
• Ranolazine (anti-angina drug)
• BZP (recreational stimulant)
• TFMPP (recreational hallucinogen)
• mCPP (recreational stimulant)
• MeOPP (recreational stimulant)
• pFPP (recreational hallucinogen)

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 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.

Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials.

• Merck Index, 11th Edition, 7431.

piperazine citrate is the main ingredient in most over-the-counter pet de-wormers.

• Piperidine

• Erowid piperazine vault
• Links to external chemical sources

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.