A8848

Arachidonoyl dopamine

≥98% (HPLC), ethanol solution

• 別名: AA-DA, Arachidonyl dopamine, N-[2,3-(4-Dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide, NADA
• 実験式（ヒル表記法）: C₂₈H₄₁NO₃
• 分子量: 439.63
• MDL番号: MFCD03412031
• UNSPSCコード: 12352116
• PubChem Substance ID: 24891376
• NACRES: NA.77

特性

• 品質水準: 200
• アッセイ: ≥98% (HPLC)
• フォーム: ethanol solution
• 薬剤管理: regulated under CDSA - not available from Sigma-Aldrich Canada
• 輸送温度: wet ice
• 保管温度: −20°C
• SMILES記法: 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

詳細

詳細

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.

アプリケーション

Used in studies of the endogenous cannabinoid system.

生物化学的／生理学的作用

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.

安全性情報

• ピクトグラム: GHS02,GHS07
• シグナルワード: Danger
• 危険有害性情報: H225,H319
• 注意書き: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• 危険有害性の分類: Eye Irrit. 2 - Flam. Liq. 2
• 保管分類コード: 3 - Flammable liquids
• WGK: WGK 3
• 引火点(°F): 57.2 °F - closed cup
• 引火点(℃): 14.0 °C - closed cup