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313998-81-1

313998-81-1 Structure

313998-81-1 Structure
IdentificationBack Directory
[Name]

(5Z,8Z,11Z,14Z)-N-(4-HYDROXY-2-METHYLPHENYL)-5,8,11,14-EICOSATETRAENAMIDE
[CAS]

313998-81-1
[Synonyms]

VDM 11
VDM 11 (in Tocrisolve 100)
VDM-11 (Solution in Ethanol)
VDM 11 (in Tocrisolve(TM) 100)
N-ARACHIDONYL-4-HYDROXY-2-METHYLANILIN
N-ARACHIDONOYL-4-HYDROXY-2-METHYLANILIN
N-(4-HYDROXY-2-METHYLPHENYL)ARACHIDONYLAMIDE
N-(4-HYDROXY-2-METHYLPHENYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
(5Z,8Z,11Z,14Z)-N-(4-hydroxy-2-methylphenyl)icosa-5,8,11,14-tetraenamide
(5Z,8Z,11Z,14Z)-N-(4-HYDROXY-2-METHYLPHENYL)-5,8,11,14-EICOSATETRAENAMIDE
5,8,11,14-Eicosatetraenamide, N-(4-hydroxy-2-methylphenyl)-, (5Z,8Z,11Z,14Z)-
N-(4-Hydroxy-2-methylphenyl)arachidonylamide, (5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide
[Molecular Formula]

C27H39NO2
[MDL Number]

MFCD04037552
[MOL File]

313998-81-1.mol
[Molecular Weight]

409.6
Chemical PropertiesBack Directory
[storage temp. ]

−20°C
[solubility ]

DMSO: >5 mg/mL, soluble
[form ]

oil
[color ]

gold
[Stability:]

Light Sensitive
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

20/21/22-42
[Safety Statements ]

23-36-45
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

Numerous analogs of arachidonoyl ethanolamide (AEA) potentiate its biological activity. This potentiation is ascribed either to inhibition of AEA reuptake into neurons, or inhibition of fatty amide acyl hydrolase (FAAH) within the neurons. 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). However, VDM11 inhibits FAAH and monoacylglycerol lipase (MAGL) and may act as an alternative FAAH substrate. At a concentration of 3 μM, VDM11, like AM404, inhibits glutamergic synaptic transmission between hippocampal neurons. 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.
[Uses]

VDM-11 is a selective inhibitor of the anandamide membrane transporter.
[Biological Activity]

A potent and selective inhibitor of the anandamide membrane transporter (AMT), in water-soluble emulsion (for details see TocrisolveTM 100). IC 50 values for inhibition of AMT are 4-11 mM. Displays negligible agonist activity at the hVR1 receptor and very weak action at CB 1 and CB 2 receptors. K i values are > 5-10 mM at CB 1 and CB 2 . Active in vivo . Also available as pure oil dissolved in ethanol ((5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide ).
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