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A8848

Sigma-Aldrich

Arachidonoyl dopamine

≥98% (HPLC), ethanol solution

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C28H41NO3
Poids moléculaire :
439.63
Numéro MDL:
MFCD03412031
Code UNSPSC :
12352116
ID de substance PubChem :
24891376
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

ethanol solution

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

MVVPIAAVGAWJNQ-DOFZRALJSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

57.2 °F - closed cup

Point d'éclair (°C)

14.0 °C - closed cup

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Hanine Barek et al.
Rapid communications in mass spectrometry : RCM, 31(16), 1363-1373 (2017-05-31)
N-β-Alanyldopamine (NBAD) and N-acetyldopamine (NADA) are catecholamines that are used by insects as sclerotizing precursors to harden their cuticle. They share a common pathway utilizing the same set of sclerotizing enzymes. Yet, cuticles using NBAD are brown, while cuticles using
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
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
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
Ken Sasaki et al.
PloS one, 13(10), e0206624-e0206624 (2018-10-30)
Caste-specific differences in the dopaminergic systems of social insects assist in maintaining caste-specific behavior. To determine how caste differences in the honey bee occur during metamorphosis, a number of comparative analyses between castes were performed including comprehensive quantification of: levels
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