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
LM ID
LMFA08020139
Formula
Exact Mass
Calculate m/z
447.358858
Status
Curated

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

Other Databases

PubChem CID
Cayman ID

Admin

Created at
-
Updated at
29th Jan 2021