N-Arachidonoyl Dopamine

Cayman Chemical Item Number 90057

NADA (CAS 199875-69-9)

N-Arachidonoyl Dopamine (CAS 199875-69-9)

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Description

Several different arachidonoyl amino acids, including N-arachidonoyl dopamine (NADA), have been isolated and characterized from bovine brain.1 NADA is the amide of the neurotransmitter dopamine and arachidonic acid. NADA is a CB1-selective agonist, inducing the typical tetrad of hypothermia, analgesia, catalepsy, and hypomotility in rats which exceeds that of anandamide (AEA).2 NADA is a full agonist at the vanilloid receptor 1, but is inactive on the dopaminergic D1 and D2 receptors. NADA is also a potent inhibitor (IC50 = 0.25 µM) of the proliferation of MCF-7 breast carcinoma cells. Recent reports of NADA’s endothelium-dependent vasodilation indicate that some of its cannabinergic activities antagonized by SR141716A may be non-CB1/CB2 dependent.3

1 Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276(46) 42639-42644 (2001).

2 Bisogno, T., Melck, D., Bobrov, M.Y., et al. N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351 817-824 (2001).

3 Randall, M., and Maxey, K.M. Personal Communication. (2003).

Synonyms
  • NADA
Formal Name N-​[2-​(3,​4-​dihydroxyphenyl)ethyl]-​5Z,​8Z,​11Z,​14Z-​eicosatetraenamide
CAS Number 199875-69-9
Molecular Formula C28H41NO3
Formula Weight 439.6
Formulation A solution in ethanol
Purity >98%
λmax 211, 284 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​NCCc1ccc(O)​c(O)​c1
InCHI Code
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​1S/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)​29-23-22-25-20-21-26(30)​27(31)​24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)​/b7-6-,10-9-,13-12-,16-15-
InCHI Key
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MVVPIAAVGAWJNQ-DOFZRALJSA-N

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N-Arachidonoyl Dopamine is available in the following screening library:

Size Price Quantity Subtotal
5 mg $42.00 $0.00
10 mg $80.00 $0.00
50 mg $336.00 $0.00
100 mg $529.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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