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A8848

Sigma-Aldrich

Arachidonoyl dopamine

≥98% (HPLC), ethanol solution

Synonym(s):

AA-DA, Arachidonyl dopamine, N-[2,3-(4-Dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide, NADA

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About This Item

Empirical Formula (Hill Notation):
C28H41NO3
Molecular Weight:
439.63
MDL number:
MFCD03412031
UNSPSC Code:
12352116
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

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

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Alcohols
Hazardous rank II

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

A8848-5MG:4548173358871
A8848-BULK:
A8848-5MG-PW:
A8848-VAR:

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’.

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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
Julie Loisel et al.
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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
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