Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110686
Identification
Name: putrescine
Description:An alkane-α,ω-diammonium(2+) that is the dication of putrescine (1,4-butanediamine) arising from protonation of both primary amino groups; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • diaminobutane
  • 1,4-diaminobutane
  • 1,4-butanediamine
  • tetramethylenediamine
Chemical Formula: C4H14N2
Average Molecular Weight: 90.168
Monoisotopic Molecular Weight: 90.1156984598
InChI Key: KIDHWZJUCRJVML-UHFFFAOYSA-P
InChI: InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2/p+2
CAS number: 110-60-1
IUPAC Name:butane-1,4-bis(aminium)
Traditional IUPAC Name: putrescine
SMILES:C([N+])CCC[N+]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
Kingdom Organic compounds
Super ClassOrganic nitrogen compounds
Class Organonitrogen compounds
Sub ClassAmines
Direct Parent Monoalkylamines
Alternative Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:+2
Melting point: 27.5 °C
Experimental Properties:
PropertyValueReference
Melting Point27.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.70SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility236.0 mg/mLALOGPS
logP-0.98ALOGPS
logP-0.85ChemAxon
logS0.43ALOGPS
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.38 m3·mol-1ChemAxon
Polarizability11.07 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-1910000000-5694141cafbe39951441View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1900000000-eeb4354250406805ebe6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-8910000000-af71049ab8358b0042ffView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-8900000000-0ba23327cabd9b2815f5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-234e1b62f4e830226779View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-e29f1004e27fcb9cfe7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-f718a117761c1c7ea80dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-47752c8c65e2d83e78fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00du-9000000000-3603b20551e892ad6c5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-001i-9000000000-224d3a5d3fbe7e1c6bd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-9000000000-5759f91b24f2e27cc466View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-00di-9000000000-226a78b715ff64ec7067View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00dr-9000000000-0b342438cba3ac71bccbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-8add450cd915232f7353View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-7a496471bdf7e391fdc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-84da87b521647b4f42abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9000000000-3ca1e2cd5a7e125ac52eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-830221d5ea74a91c32e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9000000000-896934367d7bc245c8b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9000000000-96d51f0aa46b0ab332d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-de02b50a4b8a279875e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-73c448854a91ad5a9644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-c600a93b8d737a254884View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-ce7ae61a17ef7cb9b2c2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2b410aa72c9bb951a79dView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Gimelli G, Giglio S, Zuffardi O, Alhonen L, Suppola S, Cusano R, Lo Nigro C, Gatti R, Ravazzolo R, Seri M: Gene dosage of the spermidine/spermine N(1)-acetyltransferase ( SSAT) gene with putrescine accumulation in a patient with a Xp21.1p22.12 duplication and keratosis follicularis spinulosa decalvans (KFSD). Hum Genet. 2002 Sep;111(3):235-41. Epub 2002 Aug 1. [12215835 ]
  • Janne J, Alhonen L, Pietila M, Keinanen TA: Genetic approaches to the cellular functions of polyamines in mammals. Eur J Biochem. 2004 Mar;271(5):877-94. [15009201 ]
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  • Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. [11419735 ]
  • El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. [6625645 ]
  • Reeben M, Arbatova J, Palgi J, Miettinen R, Halmekyto M, Alhonen L, Janne J, Riekkinen P Sr, Saarma M: Induced expression of neurotrophins in transgenic mice overexpressing ornithine decarboxylase and overproducing putrescine. J Neurosci Res. 1996 Sep 1;45(5):542-8. [8875319 ]
  • Takagi K, Tatsumi Y, Kitaichi K, Iwase M, Shibata E, Nakao M, Matsumoto T, Takagi K, Hasegawa T: A sensitive colorimetric assay for polyamines in erythrocytes using oat seedling polyamine oxidase. Clin Chim Acta. 2004 Feb;340(1-2):219-27. [14734216 ]
  • Harik SI, Sutton CH: Putrescine as a biochemical marker of malignant brain tumors. Cancer Res. 1979 Dec;39(12):5010-5. [227593 ]
  • Halmekyto M, Alhonen L, Alakuijala L, Janne J: Transgenic mice over-producing putrescine in their tissues do not convert the diamine into higher polyamines. Biochem J. 1993 Apr 15;291 ( Pt 2):505-8. [8484731 ]
  • Goldman SS, Volkow ND, Brodie J, Flamm ES: Putrescine metabolism in human brain tumors. J Neurooncol. 1986;4(1):23-9. [3746382 ]
  • Yamazaki H, Tsukahara T, Uki J, Matsuzaki S: Elevated levels of free putrescine and N1-acetylspermidine in cyst fluids of malignant brain tumours. J Neurol Neurosurg Psychiatry. 1986 Feb;49(2):209-10. [3950641 ]
  • Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]
  • Janne J, Alhonen L, Keinanen TA, Pietila M, Uimari A, Pirinen E, Hyvonen MT, Jarvinen A: Animal disease models generated by genetic engineering of polyamine metabolism. J Cell Mol Med. 2005 Oct-Dec;9(4):865-82. [16364196 ]
Synthesis Reference: Dudley, H. W.; Thorpe, W. V. Synthesis of N-methylputrescine and of putrescine. Biochemical Journal (1925), 19 845-9.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS110-60-1
ChEBI326268
ChemSpider2695170
HMDBHMDB01414
IAF126033980
KEGGC00134
MetaboLightsMTBLC326268
PubChem3452892