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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 02:46:53 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003661
Secondary Accession Numbers
  • HMDB0060258
  • HMDB03661
  • HMDB60258
Metabolite Identification
Common NameN-Methylputrescine
DescriptionN-Methylputrescine is a byproduct of putrescine (a diamine), via methylation by putrescine N-methyltransferase (PMT; EC 2.1.1.53). N-methylputrescine is able to affect protein synthesis to a small extent in stimulated H-35 hepatoma cells, being an inhibitor of cellular insulin-induced ornithine decarboxylase activity. (PMID: 2051998 ). Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. N-Methylputrescine is a microbial metabolite.
Structure
Data?1582752285
Synonyms
ValueSource
1-Amino-4-methylaminobutaneHMDB
N-Methyl-1,4-butanediamineHMDB
N-Methyl-1,4-diaminobutaneHMDB
N-Methylbutane-1,4-diamineHMDB
N-MethylputresciniumHMDB
N1-Methyl-1,4-butanediamineHMDB
Chemical FormulaC5H14N2
Average Molecular Weight102.1781
Monoisotopic Molecular Weight102.115698458
IUPAC Name(4-aminobutyl)(methyl)amine
Traditional NameN-methylputrescine
CAS Registry Number14475-60-6
SMILES
CNCCCCN
InChI Identifier
InChI=1S/C5H14N2/c1-7-5-3-2-4-6/h7H,2-6H2,1H3
InChI KeyRMIVMBYMDISYFZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.051Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility274 g/LALOGPS
logP-0.46ALOGPS
logP-0.41ChemAxon
logS0.43ALOGPS
pKa (Strongest Basic)10.71ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area38.05 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.15 m³·mol⁻¹ChemAxon
Polarizability13.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.16431661259
DarkChem[M-H]-117.04731661259
DeepCCS[M+H]+124.81330932474
DeepCCS[M-H]-122.87330932474
DeepCCS[M-2H]-158.33530932474
DeepCCS[M+Na]+132.92230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethylputrescineCNCCCCN1469.3Standard polar33892256
N-MethylputrescineCNCCCCN927.6Standard non polar33892256
N-MethylputrescineCNCCCCN894.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methylputrescine,1TMS,isomer #1CNCCCCN[Si](C)(C)C1146.8Semi standard non polar33892256
N-Methylputrescine,1TMS,isomer #1CNCCCCN[Si](C)(C)C1209.9Standard non polar33892256
N-Methylputrescine,1TMS,isomer #1CNCCCCN[Si](C)(C)C1453.3Standard polar33892256
N-Methylputrescine,1TMS,isomer #2CN(CCCCN)[Si](C)(C)C1170.1Semi standard non polar33892256
N-Methylputrescine,1TMS,isomer #2CN(CCCCN)[Si](C)(C)C1206.5Standard non polar33892256
N-Methylputrescine,1TMS,isomer #2CN(CCCCN)[Si](C)(C)C1779.4Standard polar33892256
N-Methylputrescine,2TMS,isomer #1CN(CCCCN[Si](C)(C)C)[Si](C)(C)C1347.3Semi standard non polar33892256
N-Methylputrescine,2TMS,isomer #1CN(CCCCN[Si](C)(C)C)[Si](C)(C)C1410.4Standard non polar33892256
N-Methylputrescine,2TMS,isomer #1CN(CCCCN[Si](C)(C)C)[Si](C)(C)C1394.8Standard polar33892256
N-Methylputrescine,2TMS,isomer #2CNCCCCN([Si](C)(C)C)[Si](C)(C)C1364.9Semi standard non polar33892256
N-Methylputrescine,2TMS,isomer #2CNCCCCN([Si](C)(C)C)[Si](C)(C)C1407.4Standard non polar33892256
N-Methylputrescine,2TMS,isomer #2CNCCCCN([Si](C)(C)C)[Si](C)(C)C1434.1Standard polar33892256
N-Methylputrescine,3TMS,isomer #1CN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1606.2Semi standard non polar33892256
N-Methylputrescine,3TMS,isomer #1CN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1605.1Standard non polar33892256
N-Methylputrescine,3TMS,isomer #1CN(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1441.2Standard polar33892256
N-Methylputrescine,1TBDMS,isomer #1CNCCCCN[Si](C)(C)C(C)(C)C1366.0Semi standard non polar33892256
N-Methylputrescine,1TBDMS,isomer #1CNCCCCN[Si](C)(C)C(C)(C)C1398.8Standard non polar33892256
N-Methylputrescine,1TBDMS,isomer #1CNCCCCN[Si](C)(C)C(C)(C)C1561.3Standard polar33892256
N-Methylputrescine,1TBDMS,isomer #2CN(CCCCN)[Si](C)(C)C(C)(C)C1400.0Semi standard non polar33892256
N-Methylputrescine,1TBDMS,isomer #2CN(CCCCN)[Si](C)(C)C(C)(C)C1393.2Standard non polar33892256
N-Methylputrescine,1TBDMS,isomer #2CN(CCCCN)[Si](C)(C)C(C)(C)C1852.9Standard polar33892256
N-Methylputrescine,2TBDMS,isomer #1CN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1797.8Semi standard non polar33892256
N-Methylputrescine,2TBDMS,isomer #1CN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1791.8Standard non polar33892256
N-Methylputrescine,2TBDMS,isomer #1CN(CCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1663.2Standard polar33892256
N-Methylputrescine,2TBDMS,isomer #2CNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1785.8Semi standard non polar33892256
N-Methylputrescine,2TBDMS,isomer #2CNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1795.4Standard non polar33892256
N-Methylputrescine,2TBDMS,isomer #2CNCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1637.8Standard polar33892256
N-Methylputrescine,3TBDMS,isomer #1CN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2216.1Semi standard non polar33892256
N-Methylputrescine,3TBDMS,isomer #1CN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2175.2Standard non polar33892256
N-Methylputrescine,3TBDMS,isomer #1CN(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1809.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Methylputrescine GC-MS (3 TMS)splash10-05i0-1900000000-611dec3293e5092fcc132014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylputrescine GC-MS (Non-derivatized)splash10-05i0-1900000000-611dec3293e5092fcc132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylputrescine GC-MS (Non-derivatized)splash10-05i0-1900000000-611dec3293e5092fcc132017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylputrescine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-17d5623d1dd5dc38bdfe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylputrescine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 0V, positive-QTOFsplash10-0udi-2900000000-b1aef2556bf106e8878a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 0V, positive-QTOFsplash10-0udi-3900000000-280be8062e4e850294642020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 0V, positive-QTOFsplash10-0udi-4900000000-27a40b8b0bc2f355ca6c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 0V, positive-QTOFsplash10-0udr-7900000000-5745b4982338078e3e6e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 0V, positive-QTOFsplash10-0uki-9500000000-f2c98b93ed164139aaf82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 1V, positive-QTOFsplash10-0fe0-9300000000-c70a92917801dfa9b9442020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 1V, positive-QTOFsplash10-0079-9200000000-88e4a5f15bce37370f382020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 1V, positive-QTOFsplash10-0079-9100000000-d0b92e199bbeb93e19f22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 1V, positive-QTOFsplash10-00dr-9000000000-5ebbf2ae7f352f43be4f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 1V, positive-QTOFsplash10-00dr-9000000000-0d6037e1a0bc35af13842020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 2V, positive-QTOFsplash10-00dr-9000000000-f3dbac9f67fb540ba1022020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 2V, positive-QTOFsplash10-00dr-9000000000-5b45f22a09525a0538eb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 3V, positive-QTOFsplash10-00dr-9000000000-ee0020efe444b664566a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 3V, positive-QTOFsplash10-00dr-9000000000-57c2a3856c1ddefa14032020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 4V, positive-QTOFsplash10-00di-9000000000-77a7b30d15c2273de3ff2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 5V, positive-QTOFsplash10-00di-9000000000-9513f55842604fb1550a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine Orbitrap 6V, positive-QTOFsplash10-00di-9000000000-d4410de8da9a29a3e9232020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylputrescine n/a 7V, positive-QTOFsplash10-000i-9000000000-50dd10d55b53bfaa8c432020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 10V, Positive-QTOFsplash10-0udr-9500000000-118703080159cff02d982015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 20V, Positive-QTOFsplash10-0pi9-9100000000-96dc6cdcb55fdb839e852015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 40V, Positive-QTOFsplash10-0a4l-9000000000-e19b9027d46da50ac4062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 10V, Negative-QTOFsplash10-0udi-1900000000-77c0c0de26c9beba29ff2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 20V, Negative-QTOFsplash10-0udi-3900000000-263082eee53d13da3cf12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 40V, Negative-QTOFsplash10-059x-9000000000-e798fd30dd01862c30c12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylputrescine 10V, Negative-QTOFsplash10-0udi-0900000000-cb1f89e0456bf50d18a02021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023211
KNApSAcK IDC00034611
Chemspider ID388845
KEGG Compound IDC02723
BioCyc IDCPD-394
BiGG ID40435
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439791
PDB IDNot Available
ChEBI ID17166
Food Biomarker OntologyNot Available
VMH IDNMPTRC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDudley, 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
General References
  1. 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 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Frydman J, Ruiz O, Robetto E, Dellacha JM, Frydman RB: Modulation of insulin induced ornithine decarboxylase by putrescine and methylputrescines in H-35 hepatoma cells. Mol Cell Biochem. 1991 Jan 16;100(1):9-23. [PubMed:2051998 ]

Enzymes

General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
N-Methylputrescine + Oxygen + Hydrogen Ion → 1-Methylpyrrolinium + Hydrogen peroxide + Ammoniadetails
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
N-Methylputrescine + Oxygen + Hydrogen Ion → 1-Methylpyrrolinium + Hydrogen peroxide + Ammoniadetails