(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide
- CAS No.
- 313998-81-1
- Chemical Name:
- (5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide
- 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
- CBNumber:
- CB4164533
- Molecular Formula:
- C27H39NO2
- Molecular Weight:
- 409.6
- MDL Number:
- MFCD04037552
- MOL File:
- 313998-81-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| storage temp. | −20°C |
|---|---|
| solubility | DMSO: >5 mg/mL, soluble |
| form | oil |
| color | gold |
| Stability | Light Sensitive |
| FDA UNII | SQF3UL3Q4C |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H312-H332-H334 | |||||||||
| Precautionary statements | P261-P280-P342+P311 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 20/21/22-42 | |||||||||
| Safety Statements | 23-36-45 | |||||||||
| WGK Germany | 3 | |||||||||
| NFPA 704 |
|
(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide price More Price(17)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | V3264 | VDM 11 Light-sensitive; store under argon. | 313998-81-1 | 5mg | $92.7 | 2022-05-15 | Buy |
| Cayman Chemical | 10006731 | VDM11 ≥98% | 313998-81-1 | 5mg | $46 | 2026-04-30 | Buy |
| Cayman Chemical | 10006731 | VDM11 ≥98% | 313998-81-1 | 10mg | $86 | 2026-04-30 | Buy |
| Cayman Chemical | 10006731 | VDM11 ≥98% | 313998-81-1 | 25mg | $202 | 2026-04-30 | Buy |
| Cayman Chemical | 10006731 | VDM11 ≥98% | 313998-81-1 | 50mg | $355 | 2026-04-30 | Buy |
(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide Chemical Properties, Uses, Production
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 ).
References
[1] LUCIANO DE PETROCELLIS . Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity[J]. FEBS Letters, 2000, 483 1: Pages 52-56. DOI: 10.1016/s0014-5793(00)02082-2
[2] SéVERINE VANDEVOORDE Christopher J F. Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: evidence that VDM11 acts as an FAAH substrate[J]. British Journal of Pharmacology, 2009, 145 7: 885-893. DOI: 10.1038/sj.bjp.0706253
[3] BROOKE G KELLEY Stanley A T. Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors[J]. European journal of pharmacology, 2004, 496 1: Pages 33-39. DOI: 10.1016/j.ejphar.2004.06.011
(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-2-methylphenyl)-5,8,11,14-eicosatetraenamide Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354; +1-00000000000 | marketing@targetmol.com | United States | 32431 | 58 |
| ChemeGen(Shanghai) Biotechnology Co.,Ltd. | 18818260767 | sales@chemegen.com | China | 11123 | 58 |
| MedBioPharmaceutical Technology Inc | 021-69568360 18916172912 | order@med-bio.cn | China | 8137 | 58 |
| Energy Chemical | 021-58432009 400-005-6266 | marketing@energy-chemical.com | China | 44871 | 58 |
| TargetMol Chemicals Inc. | 4008200310 15002144251 | marketing@tsbiochem.com | China | 24951 | 58 |
| Shaanxi Didu Pharmaceutical Co., Ltd. | 029-81124775 17791530730 | 1079@dideu.com | China | 10000 | 58 |
| Guangzhou Ruidi Biotechnology Co., Ltd. | 020-82099279 18988941402 | sales@ubiochem.com | China | 9998 | 58 |
