Arachidonoyl dopamine, (HPLC), ethanol solution, 5MG

SKU:
A8848-5MG
  • $132.00

    • Description

    Arachidonoyl dopamine ≥98% (HPLC), ethanol solution, 5MG

    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:
    MFCD03412031
    PubChem Substance ID:
    24891376
    NACRES:
    NA.77

    Quality Level

    200

    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

    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.

    Other Notes

    Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A8848.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. 

    SAFETY INFORMATION

    Pictograms

    GHS02,GHS07

    Signal Word

    Danger

    Hazard Statements

    H225 - H319

    Precautionary Statements

    P210 - P305 + P351 + P338

    RIDADR

    UN1170 - class 3 - PG 2 - Ethanol, solution

    WGK Germany

    WGK 3

    Flash Point(F)

    57.2 °F - closed cup

    Flash Point(C)

    14.0 °C - closed cup