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20-September-2008 09:55:56 - Piperazine Redirected from Piperazines Piperazine IUPAC name piperazine Other names Hexahydropyrazine Piperazidine Diethylenediamine Identifiers CAS number 110-85-0 PubChem 4837 ATC code P02CB01 SMILES C1CNCCN1 Properties Molecular formula C4H10N2 Molar mass 86.14 g mol-1 Melting point 106°C Boiling point 146°C Acidity pKa 5.68, 9.82 Pharmacology Protein binding 60-70% Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references 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 Piperazine Derivatives as Drugs 4 As an anthelmintic 5 Other uses 6 References 7 See also 8 External links Origin and naming Piperazines were originally named because of their chemical similarity with piperidine, a structural constituent of piperine in the black pepper plant Piper nigrum. Chemistry Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with a pKb 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 Derivatives as Drugs Piperazine was introduced to 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 notably successful drugs, including: Piperazine citrate antiparasitic Fluphenazine phenothiazine antipsychotic drug Perphenazine phenothiazine antipsychotic drug Prochlorperazine phenothiazine antipsychotic drug Trifluoperazine phenothiazine antipsychotic drug Flupentixol thioxanthene antipsychotic drug Thiothixene thioxanthene antipsychotic drug Zuclopenthixol thioxanthene antipsychotic drug Clozapine antipsychotic drug Olanzapine antipsychotic drug Aripiprazole antipsychotic drug Ziprasidone antipsychotic drug Bifeprunox antipsychotic drug Sildenafil impotence drug Vardenafil 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 hallucinogen mCPP stimulant MeOPP stimulant pFPP hallucinogen 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. Other uses Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials. Piperazine ferulate tablets are used as a Chinese herb and in one patient resulted in elevated liver enzymes when taken during treatment for latent tuberculosis infection with isoniazid INH. Stopping both Chinese herb and INH brought liver enzymes back to normal range within 1 month. References Merck Index, 11th ion, 7431. See also Piperidine External links Erowid piperazine vault Piperazine Reviews and Information This article incorporates text from the Encyclopædia Britannica Eleventh ion, a publication now in the public domain. v d e Antiparasitic - Anthelmintics P02 Antitrematodals benzimidazole Triclabendazole - quinoline Praziquantel, Oxamniquine - Metrifonate Antinematodals benzimidazole Mebendazole, Thiabendazole, Albendazole, Fenbendazole - Piperazine - Diethylcarbamazine - Levamisole - Ivermectin Anticestodals Taeniacide Niclosamide Retrieved from http://en..org/wiki/Piperazine Categories: Amines | Piperazines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano Lietuvių Nederlands 日本語 Polski Suomi This page was last modified on 17 August 2008, at 18:32
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