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Submit ReviewNADA
Description: Endogenous CB1 agonist; also vanilloid agonist and inhibitor of FAAH and AMT
Alternative Names: N-Arachidonyldopamine,AA-DA
Chemical Name: N-[2-(3,4-Dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological Activity for NADA
NADA is a potent endogenous cannabinoid and vanilloid receptor agonist, with no action at dopamine receptors. Selective for CB1 over CB2 receptors (Ki values are 0.25 and 12 μM respectively), and potent agonist at TRPV1 (VR1) receptors (EC50 ~ 50 nM). Metabolically stable and competitively inhibits FAAH and anandamide transport. Has cannabinoid and vanilloid actions in vivo.
Technical Data for NADA
| M. Wt | 439.64 |
| Formula | C28H41NO3 |
| Storage | Desiccate at -20°C |
| CAS Number | 199875-69-9 |
| PubChem ID | 5282105 |
| InChI Key | MVVPIAAVGAWJNQ-DOFZRALJSA-N |
| Smiles | O=C(NCCC1=CC=C(O)C(O)=C1)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for NADA
References for NADA
References are publications that support the biological activity of the product.
Bisogno et al (2000) N-acyl-DAs: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem.J. 351 817 PMID: 11042139
De Petrocellis et al (2000) Overlap 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 PMID: 11033355
Huang et al (2002) An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proc.Natl.Acad.Sci.U.S.A. 99 8400 PMID: 12060783
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Keywords: NADA, NADA supplier, Endogenous, CB1, agonists, vanilloid, inhibitors, inhibits, FAAH, AMT, TRPV1, cannabinoids, Receptors, Vanillioids, VR1, Channels, Transient, Receptor, Potential, cb1r, N-Arachidonyldopamine, AA-DA, TRPV, 1568, Tocris Bioscience
2 Citations for NADA
Citations are publications that use Tocris products. Selected citations for NADA include:
Kaszás et al (2012) Small molecule positive allosteric modulation of TRPV1 activation by vanilloids and acidic pH. PLoS One 340 152 PMID: 22005042
Pitcher et al (2007) Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia. J Pharmacol Exp Ther 3 17 PMID: 17603899
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
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Cannabinoid Receptor Ligands Scientific Review
Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.
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