6-Dimethylaminopurine

6-Dimethylaminopurine 구조식 이미지
카스 번호:
938-55-6
상품명:
6-Dimethylaminopurine
동의어(영문):
N6;DMAPY;6 DMAP;4DAMPY;NSC 401568;Dimethyladenine;6-Dimethyladenine;TIMTEC-BB SBB008765;Dimethylaminopurine;N,N-Dimethyladenine
CBNumber:
CB0421579
분자식:
C7H9N5
포뮬러 무게:
163.18
MOL 파일:
938-55-6.mol
MSDS 파일:
SDS

6-Dimethylaminopurine 속성

녹는점
259-262 °C(lit.)
끓는 점
162 °C (50 mmHg)
밀도
1.1407 (rough estimate)
굴절률
1.6380 (estimate)
인화점
110 °C
저장 조건
-20°C
용해도
메탄올: 0.1 g/mL, 투명
물리적 상태
세분화된
산도 계수 (pKa)
9.38±0.20(Predicted)
색상
황백색에서 노란색까지
BRN
7634
InChIKey
BVIAOQMSVZHOJM-UHFFFAOYSA-N
CAS 데이터베이스
938-55-6(CAS DataBase Reference)
NIST
1H-Purin-6-amine, N,N-dimethyl-(938-55-6)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기
WGK 독일 3
RTECS 번호 UO7440636
HS 번호 29335990
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.

6-Dimethylaminopurine MSDS


N,N-Dimethyl-9H-purin-6-amine

6-Dimethylaminopurine C화학적 특성, 용도, 생산

화학적 성질

white to light yellow crystal powder

용도

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.

주요 응용

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.

제조 방법

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

정의

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.

일반 설명

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 준비 용품 및 원자재

원자재

준비 용품


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