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D2629

Sigma-Aldrich

6-(Dimethylamino)purine

≥98%

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Synonym(s):
6-DMAP, N6,N6-Dimethyladenine
Empirical Formula (Hill Notation):
C7H9N5
CAS Number:
938-55-6
Molecular Weight:
163.18
Beilstein:
7634
EC Number:
213-344-3
MDL number:
MFCD00005573
PubChem Substance ID:
24893701

biological source

synthetic (organic)

Quality Level

100

Assay

≥98%

form

powder

mp

259-262 °C (lit.)

solubility

water: 50 mg/mL, clear to hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

CN(C)c1ncnc2[nH]cnc12

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

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General description

6-(Dimethylamino)purine (6-DMAP) is a purine-based metabolite with two condensed heterocyclic rings and two methyl groups linked to the amino group of the purine unit of adenine.

Application

6-(Dimethylamino)purine has been used:
  • as a supplement in GR-1 aa medium (bovine medium) for parthenogenetic activation of bovine oocytes to study its potential for embryo development
  • in the activation step during the production of nuclear transfer embryos
  • as a supplement in HCR2aa medium to activate interspecies embryos derived from interspecies somatic cell nuclear transfer (iSCNT) technique

Biochem/physiol Actions

6-(Dimethylamino)purine (6-DMAP) is a protein kinase and cyclin-dependent kinase inhibitor. It acts as a secondary metabolite and mediates RNA modification. 6-DMAP is a potent cytokinetic inhibitor and is used in parthenogenesis and meiosis studies. It is also used to promote pronuclei formation in mammalian oocytes. 6-DMAP is a dual fluorescence molecule according to femtosecond fluorescence up-conversion spectroscopy studies.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Wiebke Garrels et al.
PloS one, 6(8), e23573-e23573 (2011-09-08)
Genetic engineering can expand the utility of pigs for modeling human diseases, and for developing advanced therapeutic approaches. However, the inefficient production of transgenic pigs represents a technological bottleneck. Here, we assessed the hyperactive Sleeping Beauty (SB100X) transposon system for
Patrick Imesch et al.
Journal of ovarian research, 6, 30-30 (2013-04-20)
Oocyte in vitro maturation (IVM) and cryopreservation at the time of routine ovarian tissue freezing may be offered to cancer patients as an additional option for fertility preservation. This study aimed to investigate the developmental capacity of oocytes isolated from
Justine Collier
Current opinion in microbiology, 12(6), 722-729 (2009-09-29)
N(6)-methyl-adenines can serve as epigenetic signals for interactions between regulatory DNA sequences and regulatory proteins that control cellular functions, such as the initiation of chromosome replication or the expression of specific genes. Several of these genes encode master regulators of
Gaid Le Beux et al.
Theriogenology, 60(6), 1049-1058 (2003-08-26)
Improvement of the ability to maintain germinal vesicle stage oocytes in vitro is important for the acquisition of developmental competence. Maintaining oocytes at this stage without damaging their quality would allow synchronization of maturation and homogenization of the oocytes population.
FTIR and FT-Raman spectra of 6-(dimethylamino) purine and its theoretical studies of anharmonic vibrational analysis using quantum chemical calculations
Faizan M and Ahmad S
Vibrational Spectroscopy, 113, 103224-103224 (2021)
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