A8848
Arachidonoyl dopamine
≥98% (HPLC), ethanol solution
Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
AA-DA, Arachidonyl dopamine, N-[2,3-(4-Dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide, NADA
Empirical Formula (Hill Notation):
C28H41NO3
Molecular Weight:
439.63
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
ethanol solution
drug control
regulated under CDSA - not available from Sigma-Aldrich Canada
shipped in
wet ice
storage temp.
−20°C
SMILES string
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCc1ccc(O)c(O)c1
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
General description
The endogenous cannabinoid system is comprised of two cannabinoid-receptor subtypes (CB1 and CB2 endocannabinoids (endogenous agonists of the receptors), and other supporting proteins. This system is involved in brain neuromodulation and has been reported to affect physiological processes such as appetite, pain, and movement, as well as others. Arachidonoyl Dopamine (AA-DA) is the amide of the neurotransmitter bioactive amine, dopamine, and the polyunsaturated fatty acid, arachidonic acid. AA-DA displays cannabimimetic activity in vitro and in vivo, has been shown to activate the CB1 receptor, and is a ligand for the endogenous VR1 vanilloid receptor.
Application
Used in studies of the endogenous cannabinoid system.
Biochem/physiol Actions
AA-DA competitively inhibits fatty acid amide hydrolase (IC50 = approx. 22 μM) from N18TG2 neuroblastoma cells and inhibits binding (Ki = 0.25 μM) of the selective cannabinoid receptor subtype 1 (CB1) ligand, [3H]SR141716A, to rat brain membrane. AA-DA also inhibits the anandamide membrane transporter in BL-2H3 basophilic leukemia and C6 glioma cells. AA-DA has at least a 40 fold greater selectivity for CB1 than CB2 receptors in rat brain membranes and has been shown to be more potent than anandamide as a CB1 agonist in undifferentiated N18TG2 neuroblastoma cells. AA-DA induces hypothermia and immobility, and decreases spontaneous activity and pain perception in mice and rats, which supports its action as a CB1 agonist in vivo. AA-DA has been shown to inhibit (IC50 = 0.25 μM) proliferation of human breast MCF-7 cancer cells.
related product
Product No.
Description
Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
WGK
WGK 3
Flash Point(F)
57.2 °F
Flash Point(C)
14.0 °C
Regulatory Information
危险化学品
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
V Bezuglov et al.
Bioorganic & medicinal chemistry letters, 11(4), 447-449 (2001-03-07)
New amides of different fatty acids from the C18, C20, and C22 series with dopamine were synthesized. Pharmacological characterization in binding assays with rat brain membrane preparations and in the 'tetrad' of cannabinoid behavioral tests showed that, for these compounds
Fernando Santos-Beneit et al.
Nature communications, 8(1), 1378-1378 (2017-11-11)
The central player in bacterial cell division, FtsZ, is essential in almost all organisms in which it has been tested, with the most notable exception being Streptomyces. Streptomycetes differ from many bacteria in growing from the cell tip and undergoing
Julie Loisel et al.
PloS one, 12(10), e0186282-e0186282 (2017-10-17)
The American Southwest has experienced a series of severe droughts interspersed with strong wet episodes over the past decades, prompting questions about future climate patterns and potential intensification of weather disruptions under warming conditions. Here we show that interannual hydroclimatic
Tim Ruhl et al.
Experimental cell research, 370(2), 653-662 (2018-07-24)
Multipotent mesenchymal stromal cells (MSCs) support wound healing processes. These cells express toll-like receptors (TLRs). TLRs perform important key functions when the immune system is confronted with danger signals. TLR ligation by lipopolysaccharides (LPS) activates MSCs and induces intracellular signaling
Rakesh Kumar et al.
The Journal of biological chemistry, 291(26), 13855-13863 (2016-05-05)
Vanilloids are pain evoking molecules that serve as ligands of the "heat and capsaicin receptor" TRPV1. Binding of either endogenous or exogenous vanilloids evokes channel and subsequent neuronal activation, leading to pain sensation. Despite its pivotal physiological role, the molecular
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service