Piperazine

Basic Info

Common NamePiperazine(F05921)
2D Structure
FRCD IDF05921
CAS Number110-85-0
PubChem CID4837
FormulaC4H10N2
IUPAC Name

piperazine

InChI Key

GLUUGHFHXGJENI-UHFFFAOYSA-N

InChI

InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2

Canonical SMILES

C1CNCCN1

Isomeric SMILES

C1CNCCN1

Synonyms
        
            piperazine
        
            110-85-0
        
            Diethylenediamine
        
            Piperazin
        
            Hexahydropyrazine
        
            1,4-Diazacyclohexane
        
            Piperazidine
        
            Antiren
        
            1,4-Piperazine
        
            Diethyleneimine
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazinanes
SubclassPiperazines
Intermediate Tree NodesNot available
Direct ParentPiperazines
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsPiperazine - Azacycle - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as piperazines. These are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.

Properties

Property NameProperty Value
Molecular Weight86.138
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Complexity26.5
Monoisotopic Mass86.084
Exact Mass86.084
XLogP-1.5
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8549
Human Intestinal AbsorptionHIA+0.7652
Caco-2 PermeabilityCaco2+0.6029
P-glycoprotein SubstrateSubstrate0.7537
P-glycoprotein InhibitorNon-inhibitor0.9851
Non-inhibitor0.9960
Renal Organic Cation TransporterNon-inhibitor0.5620
Distribution
Subcellular localizationLysosome0.6869
Metabolism
CYP450 2C9 SubstrateNon-substrate0.9243
CYP450 2D6 SubstrateNon-substrate0.5478
CYP450 3A4 SubstrateNon-substrate0.8425
CYP450 1A2 InhibitorNon-inhibitor0.9165
CYP450 2C9 InhibitorNon-inhibitor0.9681
CYP450 2D6 InhibitorNon-inhibitor0.9632
CYP450 2C19 InhibitorNon-inhibitor0.9805
CYP450 3A4 InhibitorNon-inhibitor0.9928
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9900
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.5571
Non-inhibitor0.7868
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.9171
Fish ToxicityLow FHMT0.8567
Tetrahymena Pyriformis ToxicityHigh TPT0.5196
Honey Bee ToxicityLow HBT0.7202
BiodegradationNot ready biodegradable0.9436
Acute Oral ToxicityIII0.8265
Carcinogenicity (Three-class)Non-required0.6959
Model Value Unit
Absorption
Aqueous solubility1.0734LogS
Caco-2 Permeability1.0580LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6247LD50, mol/kg
Fish Toxicity3.4830pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1855pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Edible Tissues Of SwineUnited States0.1ppm
Edible Tissues Of PoultryUnited States0.1ppm
HoneyJapan0.05ppm
Other Aquatic AnimalJapan0.05ppm
CrustaceansJapan0.05ppm
Shelled MolluscasJapan0.05ppm
Other FishJapan0.05ppm
PerciformesJapan0.05ppm
AnguilliformesJapan0.05ppm
SalmoniformesJapan0.05ppm
Other Poultry,EggsJapan2ppm
Chicken,EggsJapan2ppm
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm

References

TitleJournalDatePubmed ID
Systemic Contact Dermatitis.Clin Rev Allergy Immunol2018 May 1529766368
Biotransformation of ciprofloxacin by Xylaria longipes: structure elucidation andresidual antibacterial activity of metabolites.Appl Microbiol Biotechnol2018 Jul 2130030566
Berberine-piperazine conjugates as potent influenza neuraminidase blocker.Int J Biol Macromol2018 Aug 930099043
In silico prediction and characterization of secondary metabolite biosynthetic gene clusters in the wheat pathogen Zymoseptoria tritici.BMC Genomics2017 Aug 1728818040
Crystal Structure of the Fab Fragment of an Anti-ofloxacin Antibody andExploration of Its Specific Binding.J Agric Food Chem2016 Mar 3026963935
Novel levocetirizine HCl tablets with enhanced palatability: synergistic effectof combining taste modifiers and effervescence technique.Drug Des Devel Ther2015 Sep 726379426
Preparative resolution of gatifloxacin enantiomers with pre-column esterificationstrategy and comparing their enantioselectivity to bacteria and antibody.Biomed Environ Sci2015 Feb25716569
Biotransformation of the Antibiotic Danofloxacin by Xylaria longipes Leads to an Efficient Reduction of Its Antibacterial Activity.J Agric Food Chem2015 Aug 1226189577
Determination of methyl isocyanate in outdoor residential air near metam-sodium soil fumigations.J Agric Food Chem2014 Sep 1025144617
Discovery of the highly potent fluoroquinolone-basedbenzothiazolyl-4-thiazolidinone hybrids as antibacterials.Chem Biol Drug Des2014 Jul24524270
The influences of aconitine, an active/toxic alkaloid from aconitum, on the oral pharmacokinetics of CYP3A probe drug buspirone in rats.Drug Metab Lett201425434398
An evolving role of piperazine moieties in drug design and discovery.Mini Rev Med Chem2013 Oct23895191
The exposure of highly toxic aconitine does not significantly impact the activity and expression of cytochrome P450 3A in rats determined by a novel ultra performance liquid chromatography-tandem mass spectrometric method of a specific probe buspirone.Food Chem Toxicol2013 Jan23085095
Direct fluorimetric sensing of UV-excited analytes in biological andenvironmental samples using molecularly imprinted polymer nanoparticles andfluorescence polarization.Biosens Bioelectron2012 Jun-Jul22541891
Evaluation of the extent of protein binding by means of NMR diffusion andrelaxation experiments, and automated continuous ultrafiltration.Eur J Pharm Sci2009 Jun 2819491005
Acaricidal properties of piperazine and its derivatives against house-dust and stored-food mites.Pest Manag Sci2009 Jun19253419
Blockade of hindbrain NMDA receptors containing NR2 subunits increases sucrose intake.Am J Physiol Regul Integr Comp Physiol2009 Apr19193935
Care, husbandry and diseases of the African giant rat (Cricetomys gambianus).J S Afr Vet Assoc2008 Jun18846849
Medial parabrachial nucleus neurons modulate d-fenfluramine-induced anorexia through 5HT2C receptors.Brain Res2006 Jan 516343451
The impact of natural helminth infections and supplementary protein on growthperformance of free-range chickens on smallholder farms in El Sauce, Nicaragua.Prev Vet Med2005 Jul 1215907572