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870450O

Avanti

2-AG

Avanti Research™ - A Croda Brand 870450O

Synonym(s):

2-arachidonoyl glycerol

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About This Item

Empirical Formula (Hill Notation):
C23H38O4
CAS Number:
53847-30-6
Molecular Weight:
378.55
UNSPSC Code:
12352211
NACRES:
NA.25

form

liquid

packaging

pkg of 1 × 5 mg (with screw cap/argon/foil bag (870450O-5mg))

manufacturer/tradename

Avanti Research™ - A Croda Brand 870450O

lipid type

bioactive lipids
phosphoglycerides

shipped in

dry ice

storage temp.

−70°C

SMILES string

[H]C(CO)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO

InChI

1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-

InChI key

RCRCTBLIHCHWDZ-DOFZRALJSA-N

General description

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.

Packaging

5 mL PTFE Vial with Screw Cap/Argon/Foil Bag (870450O-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Certificates of Analysis (COA)

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T P Dinh et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(16), 10819-10824 (2002-07-24)
The endogenous cannabinoids (endocannabinoids) are lipid molecules that may mediate retrograde signaling at central synapses and other forms of short-range neuronal communication. The monoglyceride 2-arachidonoylglycerol (2-AG) meets several criteria of an endocannabinoid substance: (i) it activates cannabinoid receptors; (ii) it
S Kondo et al.
FEBS letters, 429(2), 152-156 (1998-07-03)
The molecular species compositions of monoacylglycerols obtained from various rat tissues were examined by reverse-phase high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) analyses. We confirmed that 2-arachidonoylglycerol, an endogenous cannabinoid receptor agonist, is one of the most abundant
Freek J Janssen et al.
Bioorganic & medicinal chemistry letters, 26(16), 3831-3837 (2016-07-11)
2-Arachidonoylglycerol (2-AG) is an endocannabinoid that activates the cannabinoid receptors type 1 and 2. It also serves as an important lipid precursor for the eicosanoid signaling pathway. Consequently, 2-AG is involved in many physiological functions, including anxiety, food intake, inflammation
Erik Keimpema et al.
Scientific reports, 3, 2093-2093 (2013-06-29)
Endocannabinoids are small signaling lipids, with 2-arachidonoylglycerol (2-AG) implicated in modulating axonal growth and synaptic plasticity. The concept of short-range extracellular signaling by endocannabinoids is supported by the lack of trans-synaptic 2-AG signaling in mice lacking sn-1-diacylglycerol lipases (DAGLs), synthesizing
Jonathan Z Long et al.
Nature chemical biology, 5(1), 37-44 (2008-11-26)
2-Arachidonoylglycerol (2-AG) and anandamide are endocannabinoids that activate the cannabinoid receptors CB1 and CB2. Endocannabinoid signaling is terminated by enzymatic hydrolysis, a process that for anandamide is mediated by fatty acid amide hydrolase (FAAH), and for 2-AG is thought to
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