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
- MOL File:
- 938-55-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/9/4 16:42:00
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  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(6)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | D2629 | 6-(Dimethylamino)purine ≥98% | 938-55-6 | 100MG | ₹4871.25 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | D2629 | 6-(Dimethylamino)purine ≥98% | 938-55-6 | 250MG | ₹8346.08 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | D2629 | 6-(Dimethylamino)purine ≥98% | 938-55-6 | 500MG | ₹12351.33 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | D2629 | 6-(Dimethylamino)purine ≥98% | 938-55-6 | 1G | ₹25200.6 | 2022-06-14 | Buy |
| TCI Chemicals (India) | D3894 | 6-(Dimethylamino)purine | 938-55-6 | 1G | ₹6200 | 2022-05-26 | 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.
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
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| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4542 | 58 | Inquiry |
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| Clearsynth Labs | 91-22-45045900 | Maharashtra, India | 3889 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Molecraft LifeSciences Pvt Ltd | +91 (91) 6018-8881 | New Delhi, India | 760 | 0 | Inquiry |
| Corey Organics Private Ltd. | 91-40-23715528 | Andhra Pradesh, India | 211 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Manus Aktteva Biopharma LLP | +91 79 26463394 | Gujarat, India | 275 | 58 | Inquiry |
| B R D H SCIENTIFIC SUPPLIERS | 08047642302 | Nagpur, India | 46 | 58 | Inquiry |
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