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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

N-Arachidonoyl Dopamine-d8

Cayman Chemical Item Number 10007431

NADA-d8

N-Arachidonoyl Dopamine-d8

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Description

N-Arachidonoyl dopamine-d8 contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of N-arachidonoyl dopamine by GC- or LC-mass spectrometry. Several different arachidonoyl amino acids, including 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 cannabinoid 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-d8
Formal Name N-​[2-​(3,​4-​dihydroxyphenyl)ethyl]-​5Z,​8Z,​11Z,​14Z-​eicosatetraenamide-​5,​6,​8,​9,​11,​12,​14,​15-​d8
Molecular Formula C28H33D8NO3
Formula Weight 447.6
Formulation A solution in ethanol
Purity ≥99% deuterated product
λmax 205, 283 nm
Stability 1 year
Storage -20°C
Shipping Wet ice 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

Background Reading

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).

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).

Randall, M., and Maxey, K.M. Personal Communication. (2003).
Size Price Quantity Subtotal
100 µg $43.00 $0.00
500 µg $194.00 $0.00
1 mg $344.00 $0.00
5 mg $1,505.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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N-Arachidonoyl Dopamine

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