WordNet
- vermifuge used to treat infestations by roundworms or pinworms
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/12 12:42:06」(JST)
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| Piperazine[1] | |||
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IUPAC name
piperazine |
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Other names
Hexahydropyrazine; Piperazidine; Diethylenediamine |
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| Identifiers | |||
| CAS number | 110-85-0 Y | ||
| PubChem | 4837 | ||
| ChemSpider | 13835459 N | ||
| UNII | 1RTM4PAL0V Y | ||
| DrugBank | DB00592 | ||
| KEGG | D00807 Y | ||
| ChEBI | CHEBI:28568 N | ||
| ChEMBL | CHEMBL1412 N | ||
| ATC code | P02CB01 | ||
| Jmol-3D images | Image 1 | ||
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SMILES
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InChI
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| Properties | |||
| Molecular formula | C4H10N2 | ||
| Molar mass | 86.14 g mol−1 | ||
| Appearance | White crystalline solid | ||
| Melting point | 106 °C (223 °F; 379 K)[2] | ||
| Boiling point | 146 °C (295 °F; 419 K)[2] | ||
| Solubility in water | Freely soluble[2] | ||
| Acidity (pKa) | 9.8 | ||
| Basicity (pKb) | 4.19[2] | ||
| Pharmacology | |||
| Protein binding | 60-70% | ||
| Hazards | |||
| NFPA 704 |
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2
0
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |||
| N (verify) (what is: Y/N?) | |||
| 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.
Contents
- 1 Origin and naming
- 2 Chemistry
- 3 Industrial production
- 4 As an anti-helmintic
- 5 Other uses
- 6 Piperazine derivatives as drugs
- 7 See also
- 8 References
- 9 External links
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.[3]
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).[3]
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.[4] 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 and piperazine citrate are the main anthelmintic 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 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
- Ranolazine
- Trimetazidine
Antidepressants
- Amoxapine
- Befuraline
- Buspirone
- Flesinoxan
- Gepirone
- Ipsapirone
- Nefazodone
- Piberaline
- Tandospirone
- Trazodone
- Vilazodone
- Zalospirone
Antihistamines
- Buclizine
- Meclozine
- Cinnarizine
- Cyclizine
- Hydroxyzine
- Cetirizine
- Levocetirizine
- Niaprazine
Antipsychotics
- Typical
- Fluphenazine
- Perphenazine
- Trifluoperazine
- Prochlorperazine
- Thiothixene
- Flupentixol
- Zuclopenthixol
- Atypical
- Amperozide
- Aripiprazole
- Lurasidone
- Clozapine
- Olanzapine
- Perospirone
- Ziprasidone
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
- Sildenafil
- Vardenafil
Others
- 6-Nitroquipazine
- Antrafenine
- Fipexide
- Imatinib
- NSI-189
- Piperazine (itself)
- Quipazine
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
- Pyridine
- Pyrazine
- Piperidine
References
- ^ Merck Index, 11th Edition, 7431.
- ^ a b c d Merck Index, 11th Edition, 7431
- ^ a b The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co.
- ^ Ashford’s Dictionary of Industrial Chemicals, 3rd edition, 7332
External links
| Wikisource has the text of the 1911 Encyclopædia Britannica article Piperazin. |
- Piperazine citrate at Chemicalland21
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UpToDate Contents
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English Journal
- Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors.
- Kaya B1, Yurttaş L1, Sağlik BN1,2, Levent S1,2, Özkay Y1,2, Kaplancikli ZA1.
- Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2017 Dec;32(1):193-202. doi: 10.1080/14756366.2016.1247054.
- PMID 28097890
- Simple one-pot aqueous synthesis of AuPd alloy nanocrystals/reduced graphene oxide as highly efficient and stable electrocatalyst for oxygen reduction and hydrogen evolution reactions.
- Lin XX1, Zhang XF1, Wang AJ1, Fang KM1, Yuan J1, Feng JJ2.
- Journal of colloid and interface science.J Colloid Interface Sci.2017 Aug 1;499:128-137. doi: 10.1016/j.jcis.2017.03.087. Epub 2017 Mar 22.
- PMID 28365438
- Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases.
- Basu S1, Barawkar DA2, Ramdas V2, Patel M2, Waman Y2, Panmand A2, Kumar S2, Thorat S2, Naykodi M2, Goswami A2, Reddy BS2, Prasad V2, Chaturvedi S2, Quraishi A2, Menon S2, Paliwal S2, Kulkarni A2, Karande V2, Ghosh I2, Mustafa S2, De S2, Jain V2, Banerjee ER2, Rouduri SR2, Palle VP2, Chugh A2, Mookhtiar KA3.
- European journal of medicinal chemistry.Eur J Med Chem.2017 Jul 7;134:218-229. doi: 10.1016/j.ejmech.2017.04.014. Epub 2017 Apr 12.
- PMID 28415011
Japanese Journal
- REACTIVITY OF 2-(1-METHYL-1H-BENZO[d]IMIDAZOL-2-YL)-2-NITROSOACETONITRILE : A FACILE ONE-POT SYNTHESIS OF BENZIMIDAZO[1,2-a]PIPERAZINE DERIVATIVES
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(4), 824-834, 2015-04-01
- NAID 40020423231
- SYNTHESIS OF UNPROTECTED CH₂-SKIPPED PIPERAZINE-PYRIDINE ALTERNATING CYCLES WITH AZIDE END-GROUP (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 90(1), 625-630, 2015-01-01
- NAID 40020330535
- in vitroにおける共培養された正常ヒト皮膚線維芽細胞および正常ヒト臍帯静脈内皮細胞に対する4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acidの影響
- 日本外傷歯学会雑誌 11(1), 36-45, 2015
- NAID 40020758058
Related Links
- piperazine 【名】 《化学》ピペラジン 【化学式】C4H10N2 天然物からは得られ... - アルクがお届けする進化するオンライン英和・和英辞書データベース。一般的な単語や連語から、イディオム、専門用語、スラングまで幅広く収録。
- Anthelmintic drug used in the treatment of intestinal roundworm infection in humans and domestic animals (including poultry) and against pinworm infection in humans. It is administered... ... Piperazine, also called hexahydropyrazine, ...
Related Pictures
★リンクテーブル★
| リンク元 | 「駆虫薬」「ピペラジン」 |
| 拡張検索 | 「piperazine adipate」「piperazine phosphate」「chlorophenylpiperazine」 |
「駆虫薬」
- 英
- anthelmintic, anthelmintics
- ラ
- anthelmintica
- 関
http://en.wikipedia.org/wiki/Anthelmintic
| antiplatyhelmintic agents | Antitrematodals (schistosomicides) |
binds tubulin | benzimidazole (Triclabendazole#) |
| acetylcholinesterase inhibitor | phosphonic acid (metrifonate) | ||
| Other/unknown | quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen) | ||
| anticestodals (taeniacides) |
binds tubulin | benzimidazole (albendazole#) | |
| Other/unknown | salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen) | ||
| antinematodal agents (macrofilaricides) |
binds tubulin | benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole) | |
| chloride channel | macrolide (ivermectin#) | ||
| NMDA | tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel) | ||
| Other/unknown | piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine | ||
「ピペラジン」
- 英
- piperazine
- 化
- アジピン酸ピペラジン piperazine adipate, piperazine phosphate リン酸ピペラジン
- 商
- [[]]
- 関
- [[]]