ChemicalBook > CAS DataBase List > 6-Dimethylaminopurine

6-Dimethylaminopurine

Product Name
6-Dimethylaminopurine
CAS No.
938-55-6
Chemical Name
6-Dimethylaminopurine
Synonyms
N6;DMAPY;6 DMAP;4DAMPY;NSC 401568;Dimethyladenine;6-Dimethyladenine;TIMTEC-BB SBB008765;Dimethylaminopurine;N,N-Dimethyladenine
CBNumber
CB0421579
Molecular Formula
C7H9N5
Formula Weight
163.18
MOL File
938-55-6.mol
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6-Dimethylaminopurine Property

Melting point:
259-262 °C(lit.)
Boiling point:
162 °C (50 mmHg)
Density 
1.1407 (rough estimate)
refractive index 
1.6380 (estimate)
Flash point:
110 °C
storage temp. 
-20°C
solubility 
methanol: 0.1 g/mL, clear
form 
prilled
pka
9.38±0.20(Predicted)
color 
off-white to yellow
BRN 
7634
InChIKey
BVIAOQMSVZHOJM-UHFFFAOYSA-N
CAS DataBase Reference
938-55-6(CAS DataBase Reference)
NIST Chemistry Reference
1H-Purin-6-amine, N,N-dimethyl-(938-55-6)
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Safety

Hazard Codes 
WGK Germany 
3
RTECS 
UO7440636
HS Code 
29335990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D2629
Product name
6-(Dimethylamino)purine
Purity
≥98%
Packaging
100mg
Price
$53.6
Updated
2024/03/01
Sigma-Aldrich
Product number
D2629
Product name
6-(Dimethylamino)purine
Purity
≥98%
Packaging
1g
Price
$268
Updated
2024/03/01
TCI Chemical
Product number
D3894
Product name
6-(Dimethylamino)purine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$210
Updated
2024/03/01
TCI Chemical
Product number
D3894
Product name
6-(Dimethylamino)purine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$703
Updated
2024/03/01
Sigma-Aldrich
Product number
D2629
Product name
6-(Dimethylamino)purine
Purity
≥98%
Packaging
250mg
Price
$87.6
Updated
2024/03/01
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6-Dimethylaminopurine Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powder

Uses

6-Dimethylaminopurine is a serine threonine protein kinase inhibitor. It inhibits the germinal vesicle breakdown and the meiotic maturation of oocytes. It 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.

Definition

ChEBI: 6-Dimethylaminopurine is a tertiary amine that is adenine substituted at N-6 by geminal methyl groups. It is functionally related to an 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.
A purine antagonist.
In the benzodiazepine receptor (BZR) binding assay, it inhibits the binding of 1.5 nM [3H]diazepam at 100uM in rat brains.

Preparation

6-Dimethylaminopurine synthesis: 2-Methylmercapto-4-amino-6-dimethylaminopyrimidine (VI) was smoothly nitrosated in 10% acetic acid to the 5-nitrosopyrimidine (V) in 95% yield. Reduction of V with sodium hydrosulfite to the triamine (IV), followed by formylation gave the 5-formamidopyrimidine (VII) in 76% over-all yield for the two steps. Reductive formylation of V directly to VI1 with zinc and formic acid, although more rapid, was less efficient (50% yield). Ring closure of VII to 2-methyhercapto-6-dimethylaminopurine (X) was best done on a small scale by short fusion at 250°(99% yield), although boiling quinoline, formamide, or dilute alcoholic sodium hydroxide could also be employed. The latter reagent was most efficient on a large scale. Desulfurization of X with Raney nickel (7) in 1 N sodium hydroxide at 100° afforded the final product, 6-dimethylaminopurine (XII) in 43% yield.This compound was identical in all respects with the C7H9N5 moiety from puromycin (2).

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.

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.

Purification Methods

It is purified by recrystallisation from H2O, EtOH (0.32g in 10mL) or CHCl3. [Albert & Brown J Chem Soc 2060 1954, UV: Mason J Chem Soc 2071 1954.] The monohydrochloride crystallises from EtOH/Et2O, m 2 5 3o(dec) [Elion et al. J Am Chem Soc 74 411 1952], the dihydrochloride has m 225o(dec) and the picrate has m 245o (235-236.5o) [Fryth et al. J Am Chem Soc 80 2736 1958]. [Beilstein 26 III/IV 3566.]

6-Dimethylaminopurine Preparation Products And Raw materials

Raw materials

6-Chloropurine Phosphorus oxychloride 6-Hydroxypurine N,N-Dimethylaniline Dimethylamine

Preparation Products

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View Lastest Price from 6-Dimethylaminopurine manufacturers

Hefei TNJ Chemical Industry Co.,Ltd.
Product
6-Dimethylaminopurine 938-55-6
Price
US $0.00/kg
Min. Order
25kg
Purity
99%
Supply Ability
1000MT
Release date
2019-03-08
Zhuozhou Wenxi import and Export Co., Ltd
Product
6-Dimethylaminopurine 938-55-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Career Henan Chemical Co
Product
6-Dimethylaminopurine 938-55-6
Price
US $8.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10MT
Release date
2018-12-19

938-55-6, 6-DimethylaminopurineRelated Search:

Dimethyl sulfoxide DIMETHYLAMINOPYRIDINE, POLYMER-BOUND Dimethyl phthalate ETHANE 2,6-Diaminopurine 2,6-Lutidine Dimethyl ether N,N-Dimethylformamide N,N-Dimethyl-1,4-phenylenediamine Dimethyl fumarate Dimethyl sulfide PUROMYCIN AMINONUCLEOSIDE PUROMYCIN DIHYDROCHLORIDE PUROMYCIN DIHYDROCHLORIDE 6-DIMETHYLAMINOPURINE-9-RIBOSIDE,6-Dimethylaminopurine D-riboside,6-dimethylaminopurine 9-riboside*crystalline 4-Dimethylaminopyridine Purine PUROMYCIN

  • TIMTEC-BB SBB008765
  • N,N-DIMETHYL-N-(4-PYRIDINYL)AMINE
  • N,N'-DIMETHYL-4-PYRIDINAMINE
  • N6,N6-DIMETHYLADENINE
  • N4,N4-DIMETHYLPYRIDIN-4-AMINE
  • N-(4-PYRIDYL)DIMETHYLAMINE
  • 6-Dimethyladenine
  • 6-Dimethylamino-9H-purine
  • Adenine, N,N-dimethyl-
  • Adenine, N6,N6-dimethyl-
  • Dimethyladenine
  • Dimethylaminopurine
  • N(Sup6),N(sup6)-Dimethyladenine
  • N,N-Dimethyl-6-aminopurine
  • N,N-Dimethyladenine
  • Purine, 6-(dimethylamino)-
  • 6-DIMETHYLAMINOPURINE
  • 6 DMAP
  • 4-(N,N-DIMETHYLAMINO)-PYRIDINE
  • 4DAMPY
  • DIMETHYLAMINO PYRIDINE
  • DIMETHYLAMINOPYRIDINE, 4-
  • 4-dimethylamiopryidine
  • DMAPY
  • 6-DIMETHYLAMINOPURINE CRYSTALLINE
  • N,N-dimethyl-7H-purin-6-amine
  • DIMETHYLAMINOPYRIDINE, 4-(SG)
  • 6-DIMETHYLAMINOPURINE 99%
  • N,N-Dimethyl-9H-purin-6-amine
  • 6-DiMethylaMinopurine, 98% 1GR
  • NSC 401568
  • 9H-Purin-6-amine,N,N-dimethyl-
  • N6
  • 1H-Purin-6-amine, N,N-dimethyl-
  • 6,6-Dimethyladenine
  • 6-(Dimethylamino)-7H-purine
  • N,N-Dimethyl-1H-purin-6-amine
  • 6-Dimethylaminopurine,98%
  • 6-DimethylaminopurineN6,N6-Dimethyladenine
  • 6-(Dimethylamino)purine&gt
  • 6-Dimethylaminopurine USP/EP/BP
  • 6-(Dimethylamino)purine, ≥ 98.0%
  • 938-55-6
  • 1222-58-3
  • C7H9N5
  • Reagents for Oligosaccharide Synthesis
  • Condensation & Active Esterification
  • Biochemicals and Reagents
  • BioChemical
  • Nucleosides, Nucleotides, Oligonucleotides
  • Nucleoside Analogs
  • Nitrogen cyclic compounds
  • Purine
  • Nucleotides and Nucleosides
  • Bases & Related Reagents
  • Nucleotides