For research use only. Not for therapeutic Use.
N-Docosahexaenoyl dopamine (DHA-DA) is an amine conjugate of the neurotransmitter dopamine and the polyunsaturated fatty acid docosahexaenoic acid (DHA; Item No. <span class=/itemid/>90310</span>). DHA-DA is actively transported into the brain following intraperitoneal injections in mice, resulting in reduced general locomotor activity of 35-40% at a dose of 5 mg/kg. It is theorized that the DHA portion of the molecule serves as a carrier for DA through the blood-brain barrier <em>via</em> a DHA-mediated transport system. DHA-DA exhibits immune-modulating, anti-inflammatory activity in the range of 0.1-2.5 µM, suppressing the production of nitric oxide, IL-6, CCL20, MCP-1, and PGE<sub>2</sub> (Item No. <span class=/itemid/>14010</span>) in LPS-stimulated macrophages and microglial cells without affecting NF-κB activity.
| Catalog Number | R067558 |
| CAS Number | 129024-87-9 |
| Synonyms | DHA-DA;NMI 8739 |
| Molecular Formula | C30H41NO3 |
| Purity | ≥95% |
| Target | Neuronal Signaling |
| Storage | -20°C |
| IUPAC Name | (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide |
| InChI | InChI=1S/C30H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-30(34)31-25-24-27-22-23-28(32)29(33)26-27/h3-4,6-7,9-10,12-13,15-16,18-19,22-23,26,32-33H,2,5,8,11,14,17,20-21,24-25H2,1H3,(H,31,34)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18- |
| InChIKey | HXJMZRVSTICUKC-KUBAVDMBSA-N |
| SMILES | CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)NCCC1=CC(=C(C=C1)O)O |
| Reference | 1.Shashoua, V.E., and Hesse, G.W. N-Docosahexaenoyl, 3-hydroxytyramine: A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite. Life Sciences 58(16), 1347-1357 (1996). |
