Piperazine

Piperazine[1]
Identifiers
CAS number 110-85-0 YesY
PubChem 4837
ChemSpider 13835459 YesY
UNII 1RTM4PAL0V
DrugBank DB00592
KEGG D00807 N
ChEBI CHEBI:28568 N
ChEMBL CHEMBL1412 N
ATC code P02CB01
Jmol-3D images Image 1
Properties
Molecular formula C4H10N2
Molar mass 86.14 g mol−1
Appearance White crystalline solid
Melting point

106 °C, 379 K, 223 °F ([2])

Boiling point

146 °C, 419 K, 295 °F ([2])

Solubility in water Freely soluble[2]
Acidity (pKa) 4.19[2]
Pharmacology
Protein binding 60-70%
Hazards
NFPA 704
NFPA 704.svg
2
2
0
 N (verify) (what is: YesY/N?)
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

Origin and naming

Piperazines were originally named because of their chemical similarity with piperidine, a constituent of piperine in the black pepper plant (Piper nigrum). It is important to note, however, that piperazines are not derived from plants in the Piper genus.

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.

Industrial Production

Piperazine is formed as a co-product in the ammoniation of 1,2-dichloroethane or ethanolamine. These are the only routes to the chemical used commercially.[3] The piperazine is separated from the product stream, which contains ethylenediamine, diethylenetriamine and other related linear and cyclic chemicals of this type.

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. Piperazines, especially BZP and TFMPP have become an extremely common adulterant 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 methyl diethanolamine (MDEA).

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 notable successful drugs, including:

Antianginals
Antidepressants
Antihistamines
Antipsychotics
Recreational Drugs
  • 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)
  • 4-Chlorophenylpiperazine (pCPP)
  • 4-Fluorophenylpiperazine (pFPP)
  • 3-Trifluoromethylphenylpiperazine (TFMPP)
Urologicals
Others

Most of these agents can be classified as either phenylpiperazines, benzylpiperazines, diphenylmethylpiperazines (benzhydrylpiperazines), pyridinylpiperazines, pyrimidinylpiperazines, or tricyclics (with the piperazine ring attached to the heterocyclic moiety via a side chain).

See also

References

  1. ^ Merck Index, 11th Edition, 7431.
  2. ^ a b c d Merck Index, 11th Edition, 7431
  3. ^ Ashford’s Dictionary of Industrial Chemicals, 3rd edition, 7332

External links


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Look at other dictionaries:

  • Piperazine — Pipérazine Pipérazine Structure de la pipérazine Général Nom IUPAC Pipérazine …   Wikipédia en Français

  • Pipérazine — Structure de la pipérazine Général Nom IUPAC Pipérazine …   Wikipédia en Français

  • pipérazine — ● pipérazine nom féminin Dénomination courante de l hexahydropyrazine. (Longtemps employée dans le traitement de la goutte et de la lithiase urique, la pipérazine est utilisée actuellement pour le traitement des parasitoses intestinales dues aux… …   Encyclopédie Universelle

  • Piperazine — Pi*per a*zine, n. Also zin zin . [Piperidine + azote + ine.] (Chem.) A crystalline substance, {(C2H4NH)2}, formed by action of ammonia on ethylene bromide, by reduction of pyrazine, etc. It is a strong base, and is used as a remedy for gout.… …   The Collaborative International Dictionary of English

  • piperazine — [pi per′ə zēn΄, pīper′ə zēn΄; pi per′əzin, pī per′əzin; pip′ər əzēn, pip′ər əzin] n. [ PIPER(INE) + AZ + INE3] a crystalline compound, (C2H4NH) 2, used in treating worm infestations, in insecticides, etc …   English World dictionary

  • piperazine — piperazinas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė Formulę žr. priede. priedas( ai) Grafinis formatas atitikmenys: angl. piperazine rus. пиперазин ryšiai: sinonimas – heksahidropirazinas …   Chemijos terminų aiškinamasis žodynas

  • piperazine — noun Etymology: International Scientific Vocabulary piperidine + azine Date: 1889 a crystalline heterocyclic base C4H10N2 used especially as an anthelmintic …   New Collegiate Dictionary

  • piperazine — /pi per euh zeen , zin, puy , pip euhr euh /, n. Chem. 1. Also called piperazidine /pip euh raz i deen , din, puy peuh /. a colorless, crystalline, deliquescent ring compound, C4H10N2, prepared by the reaction of ethylene bromide or ethylene… …   Universalium

  • piperazine — noun /pɪˈpɛɹəziːn/ a) A saturated heterocyclic compound, CHN, containing two nitrogen atoms in a six membered ring; it is used as an anthelmintic. b) Any derivative of this compound …   Wiktionary

  • piperazine — Its former use in gout was based upon its property of dissolving uric acid in vitro, but it is ineffective in increasing uric acid excretion; its compounds are now used as anthelmintics in oxyuriasis and ascariasis. SYN: diethylenediamine. p.… …   Medical dictionary


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