N-Arachidonoyl Dopamine (CAS 199875-69-9) | Cayman Chemical
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N-Arachidonoyl Dopamine

Item № 90057
CAS № 199875-69-9
Purity ≥98%
product image
                (CAS 199875-69-9)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $42.00 0.00
     10 mg $80.00 0.00
     50 mg $336.00 0.00
     100 mg $529.00 0.00

Pricing updated 2018-11-16. Prices are subject to change without notice.

Description
Synonyms
  • NADA

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

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Technical Information
Formal Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
199875-69-9
Synonyms
  • NADA
Molecular Formula
C28H41NO3
Formula Weight
439.6
Purity
≥98%
Formulation
A solution in ethanol
λmax
211, 284 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCc1ccc(O)c(O)c1
InChI Code
InChI=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
MVVPIAAVGAWJNQ-DOFZRALJSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 1 year
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Additional Information

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References & Product Citations
Product Description References

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 The Journal of Biological Chemisty 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 Biochemistry Journal 351, 817-824 (2001).

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

Product Citations

Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS J. Lipid. Res. 58(3), 615-624 (2017).

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