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Arachidonoyl dopamine

Name: Arachidonoyl dopamine
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24891376

UNSPSC Code:

12352116

MDL number:

MFCD03412031

Assay:

≥98% (HPLC)

Form:

ethanol solution

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Properties

Quality Segment

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

Description

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 (K_i = 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.

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This Item	870430O	A1987	870432P
Sigma-Aldrich A8848 Arachidonoyl dopamine	Avanti 870430O C20:4 anandamide (AEA)	Sigma-Aldrich A1987 AM6545	Avanti 870432P C18:1 anandamide
description ≥98% (HPLC), ethanol solution	description Avanti Research^™ - A Croda Brand 870430O	description ≥98% (HPLC)	description Avanti Research^™ - A Croda Brand 870432P, powder
assay ≥98% (HPLC)	assay >99% (TLC)	assay ≥98% (HPLC)	assay >99% (TLC)
form ethanol solution	form liquid	form powder	form powder
drug control regulated under CDSA - not available from Sigma-Aldrich Canada	drug control -	drug control -	drug control -
Quality Level 200	Quality Level -	Quality Level 100	Quality Level -
storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C
shipped in wet ice	shipped in dry ice	shipped in -	shipped in dry ice