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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
Molecular Weight:
163.18
MDL Number:
MFCD00005573
MOL File:
938-55-6.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

6-Dimethylaminopurine Properties

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)
EWG's Food Scores 1
FDA UNII 649SA4S2CV
NIST Chemistry Reference 1H-Purin-6-amine, N,N-dimethyl-(938-55-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes 
WGK Germany  3
RTECS  UO7440636
HS Code  29335990

6-Dimethylaminopurine price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D2629 6-(Dimethylamino)purine ≥98% 938-55-6 100mg $53.6 2024-03-01 Buy
Sigma-Aldrich D2629 6-(Dimethylamino)purine ≥98% 938-55-6 1g $268 2024-03-01 Buy
TCI Chemical D3894 6-(Dimethylamino)purine >98.0%(HPLC)(T) 938-55-6 1g $210 2024-03-01 Buy
TCI Chemical D3894 6-(Dimethylamino)purine >98.0%(HPLC)(T) 938-55-6 5g $703 2024-03-01 Buy
Sigma-Aldrich D2629 6-(Dimethylamino)purine ≥98% 938-55-6 250mg $87.6 2024-03-01 Buy
Product number Packaging Price Buy
D2629 100mg $53.6 Buy
D2629 1g $268 Buy
D3894 1g $210 Buy
D3894 5g $703 Buy
D2629 250mg $87.6 Buy

6-Dimethylaminopurine Chemical Properties,Uses,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.

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).
synthesis of 6-Dimethylaminopurine

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.

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.]

68-94-0
938-55-6
Synthesis of 6-Dimethylaminopurine from 6-Hydroxypurine
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View Lastest Price from 6-Dimethylaminopurine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
6-(Dimethylamino)purine pictures 2024-11-19 6-(Dimethylamino)purine
938-55-6
US $29.00 / mg 99.49% 10g TargetMol Chemicals Inc.
6-Dimethylaminopurine pictures 2023-04-12 6-Dimethylaminopurine
938-55-6
US $0.00 / kg 25kg 99% 1000MT Hefei TNJ Chemical Industry Co.,Ltd.
6-Dimethylaminopurine pictures 2021-08-12 6-Dimethylaminopurine
938-55-6
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
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> 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