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Piperazine is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystal
Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
s with a saline
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
 taste.

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

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
.

razines were originally named because of their chemical similarity with piperidine
Piperidine

Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic compound amine consists of a six-membered ring containing five methylene units and one nitrogen atom....
, a structural constituent of piperine
Piperine

Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide....
 in the black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 plant (Piper nigrum).

razine is freely soluble in water and ethylene glycol
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
, but insoluble in diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
.






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Encyclopedia


Piperazine is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystal
Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
s with a saline
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
 taste.

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

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
.

Origin and naming

Piperazines were originally named because of their chemical similarity with piperidine
Piperidine

Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic compound amine consists of a six-membered ring containing five methylene units and one nitrogen atom....
, a structural constituent of piperine
Piperine

Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide....
 in the black pepper
Black pepper

Black pepper is a flowering plant vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning....
 plant (Piper nigrum).

Chemistry

Piperazine is freely soluble in water and ethylene glycol
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
, but insoluble in diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
. It is a weak base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
 with a pKb
PKB

PKB is a three-letter abbreviation that may refer to:* Panstwowy Korpus Bezpieczenstwa, a Polish underground police force during World War II* The National Awakening Party of Indonesia, from the abbreviation for its name in Indonesian...
 of 4.19; the pH
PH

pH is a measure of the Acid or Base of a solution. It is defined as the cologarithm of the Activity of dissolved hydrogen ions . Hydrogen ion activity coefficients cannot be measured experimentally, so they are based on theoretical calculations....
 of a 10% aqueous solution is 10.8-11.8. Piperazine readily absorbs water and carbon dioxide
Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
 from the air. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
 with 1,2-dichloroethane
1,2-Dichloroethane

The chemical compound 1,2-dichloroethane, commonly known by its old name of ethylene dichloride , is a chlorinated hydrocarbon, mainly used to produce vinyl chloride monomer , the major wiktionary:Precursor for polyvinyl chloride production....
, by the action of sodium
Sodium

Sodium is an element which has the symbol Na , atomic number 11, atomic mass 23 amu , and a common oxidation number +1. Sodium is a soft, silvery white, highly reactive element and is a member of the alkali metals within "group 1" ....
 and ethylene glycol
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
 on ethylene diamine
Ethylene diamine

Ethylenediamine is the organic compound with the Chemical formula C2H42. This colorless liquid with an ammonia-like odor is a strongly base amine....
 hydrochloride
Hydrochloride

In chemistry, hydrochlorides are salt s resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic Base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....
, or by reduction of pyrazine
Pyrazine

Pyrazine is a heterocyclic aromatic organic compound.Pyrazine is a symmetrical molecule with point group D2h. It is found in folic acid in the form of pterin....
 with sodium in ethanol
Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
. Piperazine is a natural product
Natural product

A natural product is a chemical compound or substance produced by a living organism - found in nature that usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design....
.

Piperazine derivatives as drugs

Piperazine was introduced to medicine
Medicine

Medicine is the art and science of healing. It encompasses a range of health care practices evolved to maintain and restore health by the prevention and treatment of illness....
 as a solvent for uric acid
Uric acid

Uric acid is an organic compound of carbon, nitrogen, oxygen and hydrogen with the formula C5H4N4O3....
. When taken into the body the drug is partly oxidized
Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
 and partly eliminated unchanged. Outside the body, piperazine has a remarkable power to dissolve uric acid and produce a soluble urate, but in clinical experience it has not proved equally successful. Lycetol, lysidine
Lysidine (chemical)

Lysidine is an imidazoline derivative.References...
 and sidonal are compounds having similar action. Many piperazine derivatives are notably successful drugs, including:

  • Piperazine citrate
    Citrate

    A citrate can refer either to the conjugate base of citric acid, , or to the esters of citric acid. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate....
     (antiparasitic)
  • Fluphenazine
    Fluphenazine

    Fluphenazine is a typical antipsychotic medication used for the treatment of psychosis such as schizophrenia and acute manic phases of bipolar disorder....
     (phenothiazine
    Phenothiazine

    Phenothiazine is the organic compound with the formula S2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Perphenazine
    Perphenazine

    Perphenazine is a typical antipsychotic psychoactive drug. Chemically, it is classified as a piperazinyl phenothiazine. It has been in clinical use for decades....
     (phenothiazine
    Phenothiazine

    Phenothiazine is the organic compound with the formula S2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Prochlorperazine
    Prochlorperazine

    Prochlorperazine is a drug that belongs to the phenothiazine class of antipsychotic agents that are used for the treatment of nausea and vertigo ....
     (phenothiazine
    Phenothiazine

    Phenothiazine is the organic compound with the formula S2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Trifluoperazine
    Trifluoperazine

    Trifluoperazine is a typical antipsychotic medication of the phenothiazine group. It has a central antiadrenergic, antidopaminergic, and minimal anticholinergic effects....
     (phenothiazine
    Phenothiazine

    Phenothiazine is the organic compound with the formula S2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Flupentixol
    Flupentixol

    Flupentixol or flupenthixol , marketed as Depixol and Fluanxol, is a typical antipsychotic drug. It is a thioxanthene, and therefore closely related to the phenothiazines....
     (thioxanthene
    Thioxanthene

    Thioxanthene is a molecule in which the oxygen atom in xanthene is replaced with a sulfur atom. Various thioxanthene derivatives are used in the treatment of schizophrenia and psychosis....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Thiothixene
    Thiothixene

    Thiothixene is a thioxanthene Medication used as a typical antipsychotic medication. It is a thioxanthene derivative and is the cis isomer of N,Ndimethyl-...
     (thioxanthene
    Thioxanthene

    Thioxanthene is a molecule in which the oxygen atom in xanthene is replaced with a sulfur atom. Various thioxanthene derivatives are used in the treatment of schizophrenia and psychosis....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Zuclopenthixol
    Zuclopenthixol

    Zuclopenthixol is a typical antipsychotic neuroleptic drug of the thioxanthene group. It mainly acts by Receptor antagonist of D1 and D2 dopamine dopamine receptor, though it also has some antihistamine activity....
     (thioxanthene
    Thioxanthene

    Thioxanthene is a molecule in which the oxygen atom in xanthene is replaced with a sulfur atom. Various thioxanthene derivatives are used in the treatment of schizophrenia and psychosis....
     antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Clozapine
    Clozapine

    Clozapine is an antipsychotic and benzodiazepine medication used in the treatment of schizophrenia. The first of the atypical antipsychotics to be developed, it was first introduced in Europe in 1971, but was voluntarily withdrawn by the manufacturer in 1975 after it was shown to cause agranulocytosis that led to death in some patients....
     (antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Olanzapine
    Olanzapine

    Olanzapine is an atypical antipsychotic, approved by the Food and Drug Administration for the treatment of: schizophrenia on September 6, 1996; depressive episodes associated with bipolar disorder, as part of the Symbyax formulation, on December 24, 2003; acute manic episodes and maintenance treatment in bipolar disorder on January 14, 2004...
     (antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Aripiprazole
    Aripiprazole

    Aripiprazole was approved by the Food and Drug Administration on November 15, 2002 for the treatment of schizophrenia, the sixth atypical antipsychotic medication of its kind....
     (antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Ziprasidone
    Ziprasidone

    Ziprasidone was the fifth atypical antipsychotic to gain FDA approval . In the United States, Ziprasidone is Food and Drug Administration approved for the treatment of schizophrenia, and the intramuscular injection form of ziprasidone is approved for acute agitation in schizophrenic patients....
      (antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Bifeprunox
    Bifeprunox

    Bifeprunox is a novel atypical antipsychotic agent which, along with SLV313, aripiprazole and SSR-181507 combines minimal D2 receptor agonism with 5-HT receptor agonism....
     (antipsychotic
    Antipsychotic

    Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
     drug)
  • Sildenafil
    Sildenafil

    Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a Medication used to treat erectile dysfunction and pulmonary hypertension ....
     (impotence drug)
  • Vardenafil
    Vardenafil

    Vardenafil is a PDE5 inhibitor used for treating impotence that is sold under the trade name Levitra , , ....
     (impotence drug)
  • Imatinib
    Imatinib

    Imatinib is a medication used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec or Glivec as its mesylate salt, imatinib mesilate ....
     (leukemia drug)
  • Meclizine
    Meclizine

    Meclizine is an antihistamine considered to be an antiemetic. It is sold under the brand names of Bonine, Bonamine, Antivert and Postafen and is most commonly used to inhibit nausea and vomiting....
     (motion sickness drug)
  • Cyclizine
    Cyclizine

    Cyclizine is an antihistamine drug used to treat nausea, vomiting and dizziness associated with motion sickness, Vertigo and post-operative following administration of general anaesthesia and opioids....
     (antiemetic antihistamine)
  • Niaprazine
    Niaprazine

    Niaprazine is a piperazine derivative drug which acts as a sedating antihistamine. It was invented in the 1970s , and is used in France, Italy and other European countries....
     (sedating antihistamine)
  • Trazodone
    Trazodone

    Trazodone is a psychoactive compound with sedative, anxiolytic, and antidepressant properties. The various manufacturers claim that the antidepressant becomes active in the first week of therapy....
     (sedating antidepressant)
  • Nefazodone
    Nefazodone

    Nefazodone hydrochloride is an antidepressant drug marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries, due to the small possibility of hepatic injury, which could lead to the need for a liver transplant, or even death....
     (analgesic antidepressant)
  • Antrafenine
    Antrafenine

    Antrafenine is a piperazine derivative drug invented in 1979. It acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen, but is not widely used as it has largely been replaced by newer drugs....
     (analgesic)
  • Befuraline
    Befuraline

    Befuraline is a piperazine derivative drug invented in Germany in the 1970s. Befuraline has stimulant and antidepressant effects and has seen some use in Germany and France, although it has never become widely used....
     (stimulant antidepressant)
  • Trelibet (stimulant antidepressant)
  • Fipexide
    Fipexide

    Fipexide is a piperazine derivative drug invented in Italy in 1983.It was used as a nootropic drug in France and Italy, mainly for the treatment of senile dementia, but is no longer in common use due to the occurrence of rare adverse drug reactions including fever and hepatitis....
     (nootropic)
  • Trimetazidine
    Trimetazidine

    Trimetazidine is a drug for angina pectoris, sometimes referred to by the brand name Vastarel MR. Each tablet contains 35 mg of trimetazidine....
     (anti-angina drug)
  • Ranolazine
    Ranolazine

    Ranolazine, sold under the trade name Ranexa by CV Therapeutics, is an antianginal medication. On January 31 2006, ranolazine was approved for use in the United States by the Food and drug administration for the treatment of chronic angina pectoris....
     (anti-angina drug)
  • BZP
    Benzylpiperazine

    Benzylpiperazine is a recreational drug with Euphoria , stimulant properties. Its dopamine and serotonin agonist mechanism of action is believed to be similar to MDMA and the effects produced by BZP are comparable to those produced by amphetamine....
     (recreational stimulant)
  • TFMPP (hallucinogen)
  • mCPP
    1-(3-Chlorophenyl)piperazine

    1-piperazine is a piperazine-based 5-HT Receptor agonist. In the mid-2000s, it has shown up in legal alternatives to illegal stimulants in New Zealand, and pills sold as ecstasy in Europe and the United States....
     (stimulant)
  • MeOPP
    MeOPP

    4-methoxyphenylpiperazine is a piperazine derivative with stimulant effects which has been sold as an ingredient in "Party pills", initially in New Zealand and subsequently in other countries around the world....
     (stimulant)
  • pFPP
    PFPP

    Parafluorophenylpiperazine is a piperazine derivative with mildly hallucinogenic and euphoric effects which has been sold as an ingredient in legal recreational drugs known as "Party pills", initially in New Zealand and subsequently in other countries around the world....
     (hallucinogen)


As an anthelmintic

Piperazine was first introduced as an anthelmintic
Anthelmintic

Anthelmintics or antihelminthics are drugs that expel parasite worms from the body, by either stunning or killing them. They may also be called vermifuges or vermicides ....
 in 1953. A large number of piperazine derivatives also have anthelmintic action. Their mode of action is generally by paralysing
Paralysis

Paralysis is the complete loss of muscle function for one or more muscle groups. Paralysis can cause loss of feeling or loss of mobility in the affected area....
 parasites, which allows the host body to easily remove or expel the invading organism. This action is mediated by its agonist
Agonist

An agonist is a term used to describe a type of Ligand or drug that binds and alters the activity of a Receptor . The ability to alter the activity of a receptor, also known as the agonist's efficacy is a property that distinguishes it from receptor antagonist, a type of receptor ligand which also binds a receptor but which does not alter t...
 effects upon the inhibitory GABA
Gabā

Gab? or gabaa, for the Cebuano people , is the concept of a non-human and non-divine, imminent Retributive justice. A sort of negative karma, it is generally seen as an evil effect on a person because of their wrongdoings or transgressions....
 (?-aminobutyric acid) receptor. Its selectivity for helminths is because vertebrates only use GABA in the CNS
CNS

CNS may refer to:In science:* Cell , Nature , and Science , acronym used to describe the three most prestigious scientific journals involved in biomedical research...
 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.

See also

  • Piperidine
    Piperidine

    Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic compound amine consists of a six-membered ring containing five methylene units and one nitrogen atom....


External links