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Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image).
The piperazines are a broad class of chemical compounds, all of which contain a piperazine functional group. Piperazine is a substance formed by the action of sodium glycol on ethylene-diamine hydrochloride, consisting of small alkaline deliquescent crystals with a saline taste and soluble in water.
Origin and naming
Piperazines were originally named because of their chemical similarity with piperidine, a constiuent of piperine in the black pepper plant (Piper nigrum). Piperazines are naturally derived from black pepper. Although piperazines occur naturally; they are occasionally artificially synthesized by reacting alcoholic ammonia with 1,2-dichloroethane.
Medicinal Use
It 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 piperazin has a remarkable power of dissolving uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Lycetol, lysidine and sidonal are bodies having similar action. Many piperazines are successful drugs. Notable piperazine drugs include:
- BZP (recreational drug)
- TFMPP (recreational drug)
- Meclizine (motion sickness drug)
- Viagra (impotence drug)
- Imatinib (leukemia drug)
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 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, and other industrial materials.
External links
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