A selective anandamide uptake inhibitor
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VDM11

Item No. 10006731

Technical Information
Formal Name
N-(4-hydroxy-2-methylphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
313998-81-1
Molecular Formula
C27H39NO2
Formula Weight
Purity
≥98%
Formulation
A 25 mg/ml solution in ethanol
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:2): .25 mg/ml
λmax
202, 231 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)Nc1ccc(O)cc1C
InChi Code
InChI=1S/C27H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-27(30)28-26-22-21-25(29)23-24(26)2/h7-8,10-11,13-14,16-17,21-23,29H,3-6,9,12,15,18-20H2,1-2H3,(H,28,30)/b8-7-,11-10-,14-13-,17-16-
InChi Key
WUZWFRWVRHLXHZ-ZKWNWVNESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    VDM11 is an AEA transport inhibitor with essentially no activity on either the central cannabinoid receptor (CB1), peripheral cannabinoid receptor (CB2), or the vanilloid receptor 1 (VR1).1 However, VDM11 inhibits FAAH and monoacylglycerol lipase (MAGL) and may act as an alternative FAAH substrate.2 At a concentration of 3 µM, VDM11, like AM404, inhibits glutamergic synaptic transmission between hippocampal neurons.3 The mechanism of this effect may be a direct action on sodium channels. Thus, the use of anandamide analogs as uptake inhibitors and interpretation of the results must be undertaken with care.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. De Petrocellis, L., Bisogno, T., Davis, B.J., et alOverlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett. 483, 52-56 (2000).

    2. Vandervoorde, S., and Fowler, C.J. Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: Evidence that VDM11 acts as an FAAH substrate. Br. J. Pharmacol. 145, 885-893 (2005).

    3. Kelley, B.G., and Thayer, S.A. Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors. Eur. J. Pharmacol. 496, 33-39 (2004).