2-AG

한글명:2-AG

카스 번호53847-30-6

상품명:2-AG

CBNumberCB5280603

분자식C23H38O4

포뮬러 무게378.55

MOL 파일53847-30-6.mol

화학적 성질

끓는 점	508.6±50.0 °C(Predicted)
밀도	0.992±0.06 g/cm3(Predicted)
인화점	2 °C
저장 조건	-20°C
용해도	DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): ~150 μg/ml
물리적 상태	아세토니트릴 용액
산도 계수 (pKa)	13.54±0.10(Predicted)
색상	Colorless to light yellow
CAS 데이터베이스	53847-30-6(CAS DataBase Reference)

위험 및 안전 성명

위험품 표기

F,Xn

위험 카페고리 넘버

11-20/21/22-36

안전지침서

26-36/37-16

유엔번호(UN No.)

UN 1648 3/PG 2

WGK 독일

NFPA 704:

	3
2		0

그림문자(GHS)

2-AG 화학적 특성, 용도, 생산

용도
2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats.
정의
ChEBI: An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.
일반 설명
2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism. 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12.
생물학적 활성
Endogenous cannabinoid ligand that acts as a potent agonist at GPR55 (EC 50 values are 3, 519 and 618 nM at GPR55, CB 1 and CB 2 respectively; K i values are 472 and 1400 nM at CB 1 and CB 2 respectively). Found in the brain at concentrations 1000-fold higher than that of anandamide.
효소 저해제
This potent endocannabinoid (FW = 378.30 g/mol; CAS 53847-30-6; Symbol: 2-AG), also known as 1,3-dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)- 5,8,11,14-eicosatetraenoate, is an endogenous agonist of the CB1, the G- protein-coupled Cannabinoid receptor type-1 found primarily in the central and peripheral nervous system. 2-AG is found at highest concentrations in the CNS, where it exerts its cannabinoid-like neuromodulatory effects. Found in milk, 2-AG plays a role in sustaining infant suckling, and the selective CB1 receptor antagonist SR141617A (N-(piperidin-1-yl)-5-(4- chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3- carboxamide) permanently prevents milk ingestion in a dose-dependent manner, when administered to mouse pups, within 1 day of birth. 2-AG is formed by phospholipase C (PLC) and diacylglycerol lipase (DAGL) from arachidonic acid-containing diacylglycerol (DAG). In the CNS, three serine-hydrolases, monoacylglycerol lipase (MAGL), a,b-hydrolase- domain-6 (ABHD6) and a,b-hydrolase-domain 12 (ABHD12) are responsible for inactivation of the primary 2-arachidonoylglycerol. Irreversible ABHD6 inhibitors show exceptional potency and selectivity in cells (<5 nM) and, at equivalent doses in mice (1 mg/kg), acting as systemic and peripherally restricted inhibitors, respectively. Indeed, selective knockdown of ABHD6 in metabolic tissues protects mice from high-fat-diet-induced obesity, hepatic steatosis, and systemic insulin resistance.

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