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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:17:07 UTC
HMDB IDHMDB0000473
Secondary Accession Numbers
  • HMDB00473
Metabolite Identification
Common Name6-Dimethylaminopurine
Description6-Dimethylaminopurine is a serine threonine protein kinase inhibitor. It inhibits the germinal vesicle breakdown and the meiotic maturation of oocytes. (PMID 2540051 ). 6-Dimethylaminopurine can be used to rtificially lengthen the pre-maturation period of oocyte growth, in vitro, by inhibiting germinal vesicle breakdown in mouse and human oocytes. (PMID: 10655310 ).
Structure
Thumb
Synonyms
ValueSource
6-(dimethylamino)PurineChEBI
6-DimethyladenineChEBI
N,N-Dimethyl-1H-purin-6-amineChEBI
N,N-Dimethyl-6-aminopurineChEBI
N,N-DimethyladenineChEBI
N(6)-DimethyladenineChEBI
6,6-DimethyladenineHMDB
6-(dimethylamino)-PurineHMDB
6-Dimethylamine purineHMDB
DimethyladenineHMDB
DMAPHMDB
N,N-Dimethyl-adenineHMDB
N6,N6-Dimethyl-adenineHMDB
N6,N6-DimethyladenineHMDB
6-DMAPMeSH
DimethylaminopurineMeSH
N(6),N(6)-DimethyladenineMeSH
Chemical FormulaC7H9N5
Average Molecular Weight163.1799
Monoisotopic Molecular Weight163.085795313
IUPAC NameN,N-dimethyl-7H-purin-6-amine
Traditional Name6-(dimethylamino)-purine
CAS Registry Number938-55-6
SMILES
CN(C)C1=NC=NC2=C1NC=N2
InChI Identifier
InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11)
InChI KeyBVIAOQMSVZHOJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 6-alkylaminopurines. These are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct Parent6-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Dialkylarylamine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP0.53ALOGPS
logP0.36ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.7 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.95 m³·mol⁻¹ChemAxon
Polarizability16.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pc-3900000000-b36f8c9c927f8edaa026View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0300-2900000000-3190d18e3cc2e66cc97dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-aab2d716306424dc0765View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9500000000-91620b9504a7308b12e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-93fb9b2f222378a415d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-c6797046cc77d63cba06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-55b592d8f334e4afae80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-266255a5066deb62d134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-716bd3f65c301c7559b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e5e0a5fa678fabe408c6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    Not Available
    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 IDFDB022062
    KNApSAcK IDNot Available
    Chemspider ID3022
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkDMAP
    METLIN ID5460
    PubChem Compound3134
    PDB ID42C
    ChEBI ID60281
    References
    Synthesis ReferenceBaker, B. R.; Joseph, Joseph P.; Schaub, Robert E. Puromycin. Synthetic studies. I. Synthesis of 6-dimethylaminopurine, a hydrolytic fragment. Journal of Organic Chemistry (1954), 19 631-7.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Rime H, Neant I, Guerrier P, Ozon R: 6-Dimethylaminopurine (6-DMAP), a reversible inhibitor of the transition to metaphase during the first meiotic cell division of the mouse oocyte. Dev Biol. 1989 May;133(1):169-79. [PubMed:2540051 ]
    2. Anderiesz C, Fong CY, Bongso A, Trounson AO: Regulation of human and mouse oocyte maturation in vitro with 6-dimethylaminopurine. Hum Reprod. 2000 Feb;15(2):379-88. [PubMed:10655310 ]