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Record Information
Version3.6
Creation Date2012-09-11 19:06:26 UTC
Update Date2016-02-11 02:25:50 UTC
HMDB IDHMDB34301
Secondary Accession NumbersNone
Metabolite Identification
Common NamePiperidine
DescriptionPiperidine is found in barley. Piperidine is present in black pepper (Piper nigrum). Piperidine is a flavouring agent Piperidine (Azinane after the Hantzsch Widman nomenclature) is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like; the name comes from the genus name Piper, which is the Latin word for pepper. Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. Piperidine is a widely used secondary amine. It is widely used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents. Piperidine has been shown to exhibit anti-platelet, antibiotic, vasodilator, anti-hypertensive and excitant functions (PMID 15158900 , 16459921 , 4010086 , 16179488 , 421736 ). Piperidine belongs to the family of Piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
Structure
Thumb
Synonyms
ValueSource
AzacyclohexaneChEBI
AzinaneChEBI
CyclopentimineChEBI
HexahydropyridineChEBI
PentamethyleneamineChEBI
PentamethyleneimineChEBI
PentamethylenimineChEBI
pipChEBI
CypentilHMDB
FEMA 2908HMDB
hexahydro-PyridineHMDB
HexazaneHMDB
PerhydropyridineHMDB
PiperidinHMDB
Piperidine ON rasta resinHMDB
Chemical FormulaC5H11N
Average Molecular Weight85.1475
Monoisotopic Molecular Weight85.089149357
IUPAC Namepiperidine
Traditional Namepiperidine
CAS Registry Number110-89-4
SMILES
C1CCNCC1
InChI Identifier
InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
InChI KeyInChIKey=NQRYJNQNLNOLGT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Food
  • Microbial
Biofunction
  • Nutrient
  • anti-hypertensive
  • anti-platelet
  • excitant
  • vasodilator
Application
  • Flavoring Agent
  • Laboratory Chemical
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP0.84Not Available
Predicted Properties
PropertyValueSource
Water Solubility124.0 mg/mLALOGPS
logP0.97ALOGPS
logP0.66ChemAxon
logS0.16ALOGPS
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.84 m3·mol-1ChemAxon
Polarizability10.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-053u-9000000000-9b296a6ad56d186eee6fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPeriodontal diseases details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012644
KNApSAcK IDNot Available
Chemspider ID7791
KEGG Compound IDC01746
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperidine
NuGOwiki LinkHMDB34301
Metagene LinkHMDB34301
METLIN IDNot Available
PubChem Compound8082
PDB IDPIP
ChEBI ID18049
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. De Marco A, De Candia M, Carotti A, Cellamare S, De Candia E, Altomare C: Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides. Eur J Pharm Sci. 2004 Jun;22(2-3):153-64. [15158900 ]
  2. Dembitsky VM: Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides. Lipids. 2005 Nov;40(11):1081-105. [16459921 ]
  3. Aisaka K, Hattori Y, Ishihara T, Morita M, Kase Y, Miyata T: The effects of piperidine and its related substances on blood vessels. Jpn J Pharmacol. 1985 Apr;37(4):345-53. [4010086 ]
  4. Patel K, Chen Y, Dennehy K, Blau J, Connors S, Mendonca M, Tarpey M, Krishna M, Mitchell JB, Welch WJ, Wilcox CS: Acute antihypertensive action of nitroxides in the spontaneously hypertensive rat. Am J Physiol Regul Integr Comp Physiol. 2006 Jan;290(1):R37-43. Epub 2005 Sep 22. [16179488 ]
  5. Nishi K, Iwasaki K, Kase Y: Actions of piperidine and dimethylphenylpiperazinium (DMPP) on afferent discharges of the cat's carotid body. Eur J Pharmacol. 1979 Feb 15;54(1-2):141-52. [421736 ]
  6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.