A CB1 receptor agonist
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Arachidonoyl Serinol

Item No. 62170

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2-hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
183718-70-9
Molecular Formula
C23H39NO3
Formula Weight
377.6
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (2:1): 1 mg/ml
SMILES
O=C(NC(CO)CO)CCC\C=C/C/C=C\C/C=C\C/C=C\CCCCC
InChi Code
InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-
InChi Key
QHELXIATGZYOIB-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $46

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    10 mg

    $86

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    50 mg

    $355

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    100 mg

    $618

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    Product Description

    2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol.3 Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (1996).

    2. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

    3. Khanolkar, A.D., Abadji, V., Lin, S., et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J. Med. Chem. 39(22), 4515-4519 (1996).