Piperazine

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Piperazine[1]
Piperazine Structural Formula V1.svg
Piperazine-3D-balls-B.png
Names
IUPAC name
piperazine
Other names
Hexahydropyrazine; Piperazidine; Diethylenediamine
Identifiers
110-85-0 YesY
ChEBI CHEBI:28568 N
ChEMBL ChEMBL1412 N
ChemSpider 13835459 N
DrugBank DB00592 YesY
Jmol 3D model Interactive image
KEGG D00807 YesY
PubChem 4837
UNII 1RTM4PAL0V YesY
  • InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2 N
    Key: GLUUGHFHXGJENI-UHFFFAOYSA-N N
  • InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
  • C1CNCCN1
Properties
C4H10N2
Molar mass 86.136 g/mol
Appearance White crystalline solid
Melting point 106 °C (223 °F; 379 K)[1]
Boiling point 146 °C (295 °F; 419 K)[1] Sublimates
Freely soluble[1]
Acidity (pKa) 9.8
Basicity (pKb) 4.19[1]
Pharmacology
ATC code P02CB01
Pharmacokinetics:
60-70%
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Piperazine is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. 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.

Origin and naming

Piperazines were originally named because of their chemical similarity with piperidine, part of the structure 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 two pKbs of 5.35 and 9.73 at 25°C.; the pH of a 10% aqueous solution of piperazine 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.

A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44°C and boils at 125-130°C.[2]

Two common salts in the form of which piperazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2.2C6H8O7 (i.e. containing 3 molecules of piperazine to 2 molecules of citric acid), and the adipate, C4H10N2.C6H10O4 (containing 1 molecule each of piperazine and adipic acid).[2]

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 anti-helmintic

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. The neuromuscular effects are thought to be caused by blocking acetylcholine at the myoneural junction. 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 vertebrates' one.

Piperazine hydrate, piperazine adipate and piperazine citrate (used to treat ascariasis and enterobiasis[4]) are the most common anthelmintic piperazine compounds. (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). Diethylcarbamazine, a derivative of piperazine, is used to treat some types of filariasis.

Other uses

Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials. Piperazines, especially BZP and TFMPP were extremely common adulterants 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

Many currently notable drugs contain a piperazine ring as part of their molecular structure. Examples include:

Antianginals

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Antidepressants

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Antihistamines

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Antiserotonergics

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Antipsychotics

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Recreational Drugs

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Urologicals

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Others

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Diphenazin: CID 94352

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. ↑ 1.0 1.1 1.2 1.3 1.4 Merck Index, 11th Edition, 7431
  2. ↑ 2.0 2.1 The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co.
  3. ↑ Ashford’s Dictionary of Industrial Chemicals, 3rd edition, 7332
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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