SKF-83566

SKF-83566 is a potent, blood-brain permeable and orally active D1-like dopamine receptor (D1DR) antagonist and a weaker competitive antagonist at the vascular 5-HT2 receptor (Ki=11 nM). SKF-83566 is a competitive DAT (dopamine transporter) inhibitor with an IC50 of 5.7 μM. SKF-83566 also shows selective inhibition for adenylyl cyclase 2 (AC2) over AC1 and AC5 in the isolated rabbit thoracic aorta. SKF-83566 can be used for research of parkinson’s disease and nicotine craving alleviation.

Product information

CAS Number: 99295-33-7

Molecular Weight: 332.23

Formula: C17H18BrNO

Chemical Name: 8-bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol

Smiles: CN1CC(C2=CC(O)=C(Br)C=C2CC1)C1C=CC=CC=1

InChiKey: XFTVOHWWEQGXLS-UHFFFAOYSA-N

InChi: InChI=1S/C17H18BrNO/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12/h2-6,9-10,15,20H,7-8,11H2,1H3

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 33.33 mg/mL (100.32 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

SKF-83566 (0.1 μM-10 μM) causes a concentration-dependent increase in peak evoked extracellular DA concentration ([DA]o) evoked by single-pulse stimulation, with a maximum 65% increase in peak evoked [DA]o with 5 μM. The EC50 value of this effect of SKF-83566 is 1.3 μM. SKF-83566 inhibited [3H]DA uptake with an IC50 of 5.73 μM. Moreover, SKF-83566 more potently inhibits the binding of [3H]CFT, a cocaine analog, with an IC50 of 0.51 μM in [3H]DA uptake and [3H]CFT binding studies. Similarly, in LLc-PK-rDAT cell, SKF-83566 also inhibits [3H]CFT binding with an IC50 of 0.77 μM in LLc-PK-rDAT cell membrane preparations.

In Vivo:

SKF 83566 hydrobromide (oral administration; 20 µg/mL; 7 days) alone has no effects on altering LTP (115%). However, combinnation of SKF 83566 and nicotine significantly blocks the enhancement of long-term synaptic potentiation (LTP) induced by pretreatment with nicotine (SKF 83566+nicotine+cocaine, 120%; nicotine+cocaine, 143%).

References:

1. Yan-You Huang, et al.D1/D5 Receptors and Histone Deacetylation Mediate the Gateway Effect of LTP in Hippocampal Dentate Gyrus.
2. Melissa A Stouffer, et al. SKF-83566, a D1-dopamine Receptor Antagonist, Inhibits the Dopamine Transporter. J Neurochem. 2011 Sep;118(5):714-20.
3. E H Ohlstein, et al. SCH 23390 and SK&F 83566 are antagonists at vascular dopamine and serotonin receptors. Eur J Pharmacol. 1985 Jan 22;108(2):205-8.
4. Jason M Conley, et al. Development of a high-throughput screening paradigm for the discovery of small-molecule modulators of adenylyl cyclase: identification of an adenylyl cyclase 2 inhibitor. J Pharmacol Exp Ther. 2013 Nov;347(2):276-87

Products are for research use only. Not for human use.