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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:52 UTC
HMDB IDHMDB0000473
Secondary Accession Numbers
  • HMDB00473
Metabolite Identification
Common Name6-Dimethylaminopurine
Description6-Dimethylaminopurine, also known as 6,6-dimethyladenine or 6-DMAP, belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines 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. 6-Dimethylaminopurine is a puromycin analog that was first identified in the spores of Streptomyces alboniger (PMID: 5019066 ). It has subsequently been identified in several algae species (PMID: 4206669 ). 6-DMAP is widely used in the lab as a cell cycle inhibitor and a cyclin dependent kinase inhibitor. It also induces cell apoptosis. 6-DMAP is widely used for oocyte activation in eukaryotic cloning experiments (PMID: 29467049 ).
Structure
Data?1676999692
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-DMAPHMDB
DimethylaminopurineHMDB
N(6),N(6)-DimethyladenineHMDB
6-DimethylaminopurineChEBI
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
Description Belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP0.53ALOGPS
logP0.36ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)3.35ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.99331661259
DarkChem[M-H]-131.62431661259
AllCCS[M+H]+135.48332859911
AllCCS[M-H]-133.46832859911
DeepCCS[M+H]+132.55330932474
DeepCCS[M-H]-130.06130932474
DeepCCS[M-2H]-166.45630932474
DeepCCS[M+Na]+141.44830932474
AllCCS[M+H]+135.532859911
AllCCS[M+H-H2O]+131.032859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-133.532859911
AllCCS[M+Na-2H]-134.332859911
AllCCS[M+HCOO]-135.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-DimethylaminopurineCN(C)C1=NC=NC2=C1NC=N22061.4Standard polar33892256
6-DimethylaminopurineCN(C)C1=NC=NC2=C1NC=N21819.8Standard non polar33892256
6-DimethylaminopurineCN(C)C1=NC=NC2=C1NC=N21933.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Dimethylaminopurine,1TMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N21813.1Semi standard non polar33892256
6-Dimethylaminopurine,1TMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N21735.4Standard non polar33892256
6-Dimethylaminopurine,1TMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N22588.0Standard polar33892256
6-Dimethylaminopurine,1TBDMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22018.3Semi standard non polar33892256
6-Dimethylaminopurine,1TBDMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N21914.0Standard non polar33892256
6-Dimethylaminopurine,1TBDMS,isomer #1CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22657.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Dimethylaminopurine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pc-3900000000-b36f8c9c927f8edaa0262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Dimethylaminopurine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Dimethylaminopurine 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 - 6-Dimethylaminopurine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0300-2900000000-3190d18e3cc2e66cc97d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Dimethylaminopurine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03di-0900000000-aab2d716306424dc07652012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Dimethylaminopurine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-9500000000-91620b9504a7308b12e62012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Positive-QTOFsplash10-03di-0900000000-93fb9b2f222378a415d72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Positive-QTOFsplash10-03di-0900000000-c6797046cc77d63cba062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Positive-QTOFsplash10-014i-0900000000-55b592d8f334e4afae802015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Negative-QTOFsplash10-03di-0900000000-266255a5066deb62d1342015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Negative-QTOFsplash10-03di-0900000000-716bd3f65c301c7559b12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Negative-QTOFsplash10-014i-1900000000-e5e0a5fa678fabe408c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Negative-QTOFsplash10-03di-0900000000-b97707ac300bd819a7b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Negative-QTOFsplash10-03di-0900000000-6839a2c33d8f3a09762d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Negative-QTOFsplash10-014j-2900000000-9a0db3b19e645c7456222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Positive-QTOFsplash10-03di-0900000000-9cc41a9352cce06edd8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Positive-QTOFsplash10-03di-0900000000-9cc41a9352cce06edd8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Positive-QTOFsplash10-0gbc-9100000000-958df0634af1082fff3f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022062
KNApSAcK IDC00032053
Chemspider ID3022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5460
PubChem Compound3134
PDB IDNot Available
ChEBI ID60281
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  3. Sarngadharan MG, Pogell BM, Kariya M: Occurrence of new metabolites containing N 6 ,N 6 -dimethyladenine in spores of Streptomyces alboniger. Biochim Biophys Acta. 1972 Apr 12;262(4):405-9. doi: 10.1016/0005-2787(72)90483-2. [PubMed:5019066 ]
  4. Pakhomova MV: [N6-dimethylaminopurine in DNA of algae species]. Dokl Akad Nauk SSSR. 1974 Feb 11;214(5):1202-5. [PubMed:4206669 ]
  5. Kochan J, Nowak A, Nizanski W, Prochowska S, Migdal A, Mlodawska W, Partyka A, Witkowski M: Developmental competence of cat (Felis domesticus) oocytes and embryos after parthenogenetic stimulation using different methods. Zygote. 2018 Feb 22:1-8. doi: 10.1017/S0967199418000011. [PubMed:29467049 ]