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Merck
CN

A8973

2-Arachidonyl glycerol

≥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:
Molecular Weight:
378.55
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name

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

SMILES string

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

InChI key

RCRCTBLIHCHWDZ-DOFZRALJSA-N

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-

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

Quality Level

Gene Information

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

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Biochem/physiol Actions

Endogenous cannabinoid receptor agonist.

Disclaimer

Air sensitive

Physical form

acetonitrile solution

pictograms

FlameExclamation mark

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

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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Jyotpal Singh et al.
The Canadian journal of neurological sciences. Le journal canadien des sciences neurologiques, 47(3), 289-300 (2020-02-08)
Cannabidiol (CBD) has been generating increasing interest in medicine due to its therapeutic properties and an apparent lack of negative side effects. Research has suggested that high dosages of CBD can be taken acutely and chronically with little to no
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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