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A8973

2-Arachidonyl glycerol

Name: 2-Arachidonyl glycerol
Brand: SIGMA

≥98% (HPLC), Endogenous cannabinoid receptor agonist, solution

Synonym(s):

(all-Z)-5,8,11,14-Eicosatetraenoic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester, 2-AG, 2-Arachidonoylglycerol, 2-Monoarachidonoylglycerol

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₈O₄

CAS Number:

53847-30-6

Molecular Weight:

378.55

UNSPSC Code:

12352200

PubChem Substance ID:

24891388

NACRES:

NA.77

MDL number:

MFCD01862600

Assay:

≥98% (HPLC)

Form:

solution

Quality level:

100

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Product Name

2-Arachidonyl glycerol, ~10 mg/mL, ≥98% (HPLC)

description

9:1 mixture of 2-AG and 1-AG

Quality Level

100

assay

≥98% (HPLC)

form

solution

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

concentration

~10 mg/mL

shipped in

wet ice

storage temp.

−20°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

Gene Information

human ... FAAH(2166)
rat ... Cnr1(25248), Cnr2(57302)

Related Categories

Bioactive Small Molecules

Bioactive Small Molecule Agonists

Biochem/physiol Actions

Endogenous cannabinoid receptor agonist.

Physical form

acetonitrile solution

Disclaimer

Air sensitive

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H302 + H312 + H332,H319

pcodes

P210 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

35.6 °F - closed cup

flash_point_c

2 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品

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Membrane microdomains and metabolic pathways that define anandamide and 2-arachidonyl glycerol biosynthesis and breakdown.

Ekaterina A Placzek et al.

Neuropharmacology, 55(7), 1095-1104 (2008-09-02)

Anandamide (AEA) and 2-arachidonyl glycerol (2-AG), endogenous ligands for the CB1 and CB2 cannabinoid receptors, are referred to as endocannabinoids because they mimic the actions of delta9-tetrahydrocannabinol (Delta9-THC), a plant-derived cannabinoid. The processes by which AEA and 2-AG are biosynthesized

New insights into endocannabinoid degradation and its therapeutic potential.

M Bari et al.

Mini reviews in medicinal chemistry, 6(3), 257-268 (2006-03-07)

Endocannabinoids are amides, esters and ethers of long chain polyunsaturated fatty acids, which act as new lipidic mediators. Anandamide (N-arachidonoylethanolamine; AEA) and 2-arachidonoylglycerol (2-AG) are the main endogenous agonists of cannabinoid receptors, able to mimic several pharmacological effects of (-)-Delta9-tetrahydrocannabinol

CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release.

Katarzyna Malenczyk et al.

The Journal of biological chemistry, 288(45), 32685-32699 (2013-10-04)

Endocannabinoid signaling has been implicated in modulating insulin release from β cells of the endocrine pancreas. β Cells express CB1 cannabinoid receptors (CB1Rs), and the enzymatic machinery regulating anandamide and 2-arachidonoylglycerol bioavailability. However, the molecular cascade coupling agonist-induced cannabinoid receptor

The antinociceptive effects of intraplantar injections of 2-arachidonoyl glycerol are mediated by cannabinoid CB2 receptors.

J Guindon et al.

British journal of pharmacology, 150(6), 693-701 (2006-12-21)

2-arachidonoyl glycerol (2-AG) is an endogenous cannabinoid with central antinociceptive properties. Its degradation is catalysed by monoacylglycerol lipase (MGL) whose activity is inhibited by URB602, a new synthetic compound. The peripheral antinociceptive effects of 2-AG and URB602 in an inflammatory

Effects of putative cannabinoid receptor ligands, anandamide and 2-arachidonyl-glycerol, on immune function in B6C3F1 mouse splenocytes.

M Lee et al.

The Journal of pharmacology and experimental therapeutics, 275(2), 529-536 (1995-11-01)

Anandamide (arachidonylethanolamide), isolated from the porcine brain, and 2-arachidonyl-glycerol (2-Ara-Gl), derived from the canine gut, are two recently identified putative endogenous cannabinoid receptor ligands. Both ligands have been reported to possess binding affinity for cannabinoid receptor subtypes, CB1 and CB2.

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Global Trade Item Number

SKU	GTIN
A8973-5MG	04061833401033

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