Synonym: 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
Linear Formula: C28H41NO3
Product Type: Chemical
| assay |
≥98% (HPLC) |
| drug control |
regulated under CDSA - not available from Sigma-Aldrich Canada |
| form |
ethanol solution |
| 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 |
| Quality Level |
200  |
| shipped in |
wet ice |
| SMILES string |
CCCCCC=C/CC=C/CC=C/CC=C/CCCC(=O)NCCc1ccc(O)c(O)c1 |
| storage temp. |
−20°C |
| 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. |
| 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. |
| Symbol |
  GHS02,GHS07 |
| Signal word |
Danger |
| Hazard statements |
H225 - H319 |
| Precautionary statements |
P210 - P305 + P351 + P338 |
| Hazard Codes |
F |
| Risk Statements |
11 |
| Safety Statements |
16 |
| 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 |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352116 |
