A potent endocannabinoid uptake inhibitor
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WOBE437

Item No. 23506

Technical Information
Formal Name
(2E,4E)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2,4-dodecadienamide
CAS Number
2108100-73-6
Molecular Formula
C22H33NO3
Formula Weight
Purity
≥97%
Formulation
A crystalline solid
DMF: 2.5 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 1 mg/ml
λmax
254 nm
SMILES
COC1=CC=C(CCNC(/C=C/C=C/CCCCCCC)=O)C=C1OC
InChi Code
InChI=1S/C22H33NO3/c1-4-5-6-7-8-9-10-11-12-13-22(24)23-17-16-19-14-15-20(25-2)21(18-19)26-3/h10-15,18H,4-9,16-17H2,1-3H3,(H,23,24)/b11-10+,13-12+
InChi Key
LAHLFCSEHHJQRN-AQASXUMVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    WOBE437 is a potent endocannabinoid uptake inhibitor with IC50 values of 10 and 283 nM for arachidonoyl ethanolamide (AEA; Item No. 90050) and 2-arachidonoyl glycerol (2-AG; Item No. 62160) uptake, respectively, in U937 cells.1 It is greater than 1,000-fold selective for endocannabinoid transporters over fatty acid amide hydrolase (FAAH; Item No. 10010183) and the 2-AG hydrolyzing enzymes MAGL, ABHD6, and ABHD12. WOBE437 inhibits AEA uptake in FAAH-deficient HMC-1 human mast cells and Neuro2a mouse neuroblastoma cells (IC50s = 137 and 55 nM, respectively) and reduces AEA uptake by 50% in rat cortical neurons when used at a concentration of 1 μM. It also reduces 2-AG uptake by 40% in Neuro2a cells at a concentration of 5 μM. In vivo, WOBE437 increases AEA and 2-AG levels by 1.5-fold in mouse brain but not peripheral tissues after intraperitoneal administration of a 10 mg/kg dose for seven days. WOBE437 (10 mg/kg) also induces a typical tetrad of hypothermia, catalepsy, analgesia, and hypomotility in mice, indicating it also acts as an indirect cannabinoid (CB) receptor 1 agonist.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chicca, A., Nicolussi, S., Bartholomäus, R., et alChemical probes to potently and selectively inhibit endocannabinoid cellular reuptake. Proc. Natl. Acad. Sci. USA 114(25), E5006-E5015 (2017).