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| | 6-Dimethylaminopurine Basic information |
| | 6-Dimethylaminopurine Chemical Properties |
| Melting point | 259-262 °C(lit.) | | Boiling point | 162 °C (50 mmHg) | | density | 1.1407 (rough estimate) | | refractive index | 1.6380 (estimate) | | Fp | 110 °C | | storage temp. | -20°C | | solubility | methanol: 0.1 g/mL, clear | | pka | 9.38±0.20(Predicted) | | form | prilled | | 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) |
| Hazard Codes | | | WGK Germany | 3 | | RTECS | UO7440636 | | HS Code | 29335990 |
| | 6-Dimethylaminopurine Usage And Synthesis |
| 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 |
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