Structure Database (LMSD)
Common Name
N-arachidonoyl-dopamine-d8
Systematic Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide-5,6,8,9,11,12,14,15-d8
Synonyms
3D model of N-arachidonoyl-dopamine-d8
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
N-Arachidonoyl dopamine-d8 is intended for use as an internal standard for the quantification of N-arachidonoyl dopamine by GC- or LC-MS. 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
This information has been provided by Cayman Chemical
References
1. Randall, M., and Maxey, K.M. Personal Communication. (2003).
References
Comments
Synthetic deuterated standard
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
synthetic construct
(#32630)
Synthetic deuterated standard
String Representations
InChiKey (Click to copy)
MVVPIAAVGAWJNQ-FBFLGLDDSA-N
InChi (Click to copy)
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-/i6D,7D,9D,10D,12D,13D,15D,16D
SMILES (Click to copy)
C(/[2H])(=C(/[2H])\C/C(/[2H])=C(/[2H])\CCCC(=O)NCCC1=CC(O)=C(O)C=C1)\C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\CCCCC
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Created at
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Updated at
29th Jan 2021