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A8973

Sigma-Aldrich

2-Arachidonyl glycerol

~10 mg/mL, ≥98% (HPLC)

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
MDL number:
MFCD01862600
UNSPSC Code:
12352200
PubChem Substance ID:
24891388
NACRES:
NA.77

description

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

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)

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Biochem/physiol Actions

Endogenous cannabinoid receptor agonist.

Caution

Air sensitive

Physical form

acetonitrile solution

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

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_germany

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

U4133

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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.
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
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
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
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
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