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
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
- biological source
- synthetic (organic)
- Water Solubility
- water: 50mg/mL, clear to hazy, colorless to light 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)
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.
N-Bromosuccinimide Price
- Product number
- D2629
- Product name
- 6-(Dimethylamino)purine
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $53.6
- Updated
- 2024/03/01
- Product number
- D2629
- Product name
- 6-(Dimethylamino)purine
- Purity
- ≥98%
- Packaging
- 1g
- Price
- $268
- Updated
- 2024/03/01
- Product number
- D3894
- Product name
- 6-(Dimethylamino)purine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $210
- Updated
- 2024/03/01
- Product number
- D3894
- Product name
- 6-(Dimethylamino)purine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $703
- Updated
- 2024/03/01
- Product number
- D2629
- Product name
- 6-(Dimethylamino)purine
- Purity
- ≥98%
- Packaging
- 250mg
- Price
- $87.6
- Updated
- 2024/03/01
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).
Origin
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 ).
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
Preparation Products
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View Lastest Price from 6-Dimethylaminopurine manufacturers
- Product
- 6-Dimethylaminopurine 938-55-6
- Price
- US $0.00/kg
- Min. Order
- 25kg
- Purity
- 99%
- Supply Ability
- 1000MT
- Release date
- 2019-03-08
- 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
- Product
- 6-Dimethylaminopurine 938-55-6
- Price
- US $8.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10MT
- Release date
- 2018-12-19