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Showing NP-Card for 6-Dimethylaminopurine (NP0001483)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:06 UTC
NP-MRD IDNP0001483
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001483 (6-Dimethylaminopurine)

6-Dimethylaminopurine.mol
  Mrv1652305271900002D          

 12 13  0  0  0  0            999 V2000
    0.8643    0.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -1.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for NP0001483 (6-Dimethylaminopurine)

HMDB0000473
     RDKit          3D
6-Dimethylaminopurine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.9879    0.1943   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.0353    0.3297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049    0.5185    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -0.5604    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -1.6744    1.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.2457    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -1.6706    0.5283 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.5494   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775    0.2283   -0.9609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.2520   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    1.1305   -1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0367   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.1700   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583    1.2394   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -0.4377   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.5042    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    0.6422    2.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -0.1323    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.1506    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7155    2.0531   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    1.7567   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  4  1  0
 12  8  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0001483 (6-Dimethylaminopurine)

6-Dimethylaminopurine.mol
  Mrv1652305271900002D          

 12 13  0  0  0  0            999 V2000
    0.8643    0.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -1.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001483

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
BVIAOQMSVZHOJM-UHFFFAOYSA-N

> <FORMULA>
C7H9N5

> <MOLECULAR_WEIGHT>
163.1799

> <EXACT_MASS>
163.085795313

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.31681816805774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-7H-purin-6-amine

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.3634995819999999

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.185405008874447

> <JCHEM_PKA_STRONGEST_BASIC>
3.352502039178554

> <JCHEM_POLAR_SURFACE_AREA>
57.7

> <JCHEM_REFRACTIVITY>
47.9477

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(dimethylamino)-purine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001483 (6-Dimethylaminopurine)

HMDB0000473
     RDKit          3D
6-Dimethylaminopurine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.9879    0.1943   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.0353    0.3297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049    0.5185    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -0.5604    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -1.6744    1.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.2457    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -1.6706    0.5283 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.5494   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775    0.2283   -0.9609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.2520   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    1.1305   -1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0367   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.1700   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583    1.2394   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -0.4377   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.5042    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    0.6422    2.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -0.1323    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.1506    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7155    2.0531   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    1.7567   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  4  1  0
 12  8  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

PDB for NP0001483 (6-Dimethylaminopurine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6-Dimethylaminopurine.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       1.613   0.091   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.519  -1.155   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.613  -2.401   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.149  -1.925   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.185  -2.695   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.519  -1.925   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.519  -0.385   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.185   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.149  -0.385   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.185   1.925   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.519   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.149   2.695   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    1    4                                                  
CONECT   10   11   12    8                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for NP0001483 (6-Dimethylaminopurine)

COMPND    HMDB0000473
HETATM    1  C1  UNL     1      -1.988   0.194  -0.945  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.298   0.035   0.330  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.005   0.518   1.506  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.008  -0.560   0.405  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.239  -1.674   1.119  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.454  -2.246   1.198  1.00  0.00           C  
HETATM    7  N3  UNL     1       2.466  -1.671   0.528  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.277  -0.549  -0.206  1.00  0.00           C  
HETATM    9  N4  UNL     1       3.077   0.228  -0.961  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.379   1.252  -1.492  1.00  0.00           C  
HETATM   11  N5  UNL     1       1.087   1.130  -1.066  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.026   0.037  -0.285  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.051  -0.170  -0.837  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.058   1.239  -1.265  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.528  -0.438  -1.730  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.456   1.504   1.200  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.317   0.642   2.379  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.877  -0.132   1.757  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.578  -3.151   1.798  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.715   2.053  -2.141  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.285   1.757  -1.292  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4
CONECT    3   16   17   18
CONECT    4    5    5   12
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8
CONECT    8    9   12   12
CONECT    9   10   10
CONECT   10   11   20
CONECT   11   12   21
END
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SMILES for NP0001483 (6-Dimethylaminopurine)

CN(C)C1=NC=NC2=C1NC=N2
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INCHI for NP0001483 (6-Dimethylaminopurine)

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)
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View in JSmol
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 Mass163.1799 Da
Monoisotopic Mass163.08580 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Spiraea formosanaKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
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)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
HMDB IDHMDB0000473
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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. Grupen CG, Mau JC, McIlfatrick SM, Maddocks S, Nottle MB: Effect of 6-dimethylaminopurine on electrically activated in vitro matured porcine oocytes. Mol Reprod Dev. 2002 Jul;62(3):387-96. doi: 10.1002/mrd.10126. [PubMed:12112604 ]
  4. Schwalb NK, Temps F: A modified four-state model for the "dual fluorescence" of N(6),N(6)-dimethyladenine derived from femtosecond fluorescence spectroscopy. J Phys Chem A. 2009 Nov 26;113(47):13113-23. doi: 10.1021/jp9021773. [PubMed:19569655 ]
  5. Pitner TP, Glickson JD: H nuclear magnetic resonance study of restricted internal rotation of N-6,N-6-dimethyladenine in aqueous solution. Biochemistry. 1975 Jul 15;14(14):3083-7. doi: 10.1021/bi00685a007. [PubMed:238583 ]
  6. 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 ]
  7. Pakhomova MV: [N6-dimethylaminopurine in DNA of algae species]. Dokl Akad Nauk SSSR. 1974 Feb 11;214(5):1202-5. [PubMed:4206669 ]
  8. 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 ]