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A8973

Sigma-Aldrich

2-Arachidonyl glycerol

~10 mg/mL, ≥98% (HPLC)

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

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)

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Biochem/physiol Actions

Endogenous cannabinoid receptor agonist.

Caution

Air sensitive

Physical form

acetonitrile solution

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

35.6 °F

Flash Point(C)

2 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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
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
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
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
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