99295-33-7

99295-33-7 structure

Name: SKF-83566
Chemical Name: 8-Bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-olhydrobromide
CAS Number: 99295-33-7
Molecular Formula: C₁₇H₁₉BrClNO
Molecular Weight: 368.69600
Catalog: Signaling Pathways GPCR/G Protein 5-HT Receptor
Create Date: 2018-12-28 19:37:41
Modify Date: 2024-06-20 12:22:48
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)[1][3]. SKF-83566 is a competitive DAT (dopamine transporter) inhibitor with an IC50 of 5.7 μM[2]. SKF-83566 also shows selective inhibition for adenylyl cyclase 2 (AC2) over AC1 and AC5 in the isolated rabbit thoracic aorta[4]. SKF-83566 can be used for research of parkinson’s disease and nicotine craving alleviation[5].

Name	8-Bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-olhydrobromide

Description	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)[1][3]. SKF-83566 is a competitive DAT (dopamine transporter) inhibitor with an IC50 of 5.7 μM[2]. SKF-83566 also shows selective inhibition for adenylyl cyclase 2 (AC2) over AC1 and AC5 in the isolated rabbit thoracic aorta[4]. SKF-83566 can be used for research of parkinson’s disease and nicotine craving alleviation[5].
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Adenylate Cyclase Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Target	D1 Receptor D5 Receptor 5-HT2 Receptor:11 nM (Ki)
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[2]. 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[2].
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%)[1]. Animal Model: Male C57BL6/J mice (6- to 9-wk-old)[1] Dosage: 20 µg/mL (Together with nicotine for 7 d, followed by the injection of cocaine) Administration: Oral administration; 7 days Result: Blocked nicotine and cocaine-induced facilitation of LTP.
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 [5]. Yan-You Huang, et al. D1/D5 receptors and histone deacetylation mediate the Gateway Effect of LTP in hippocampal dentate gyrus. Learn Mem. 2014 Feb 18;21(3):153-60. doi: 10.1101/lm.032292.113.

Boiling Point	447.5ºC at 760mmHg
Molecular Formula	C₁₇H₁₉BrClNO
Molecular Weight	368.69600
Flash Point	224.4ºC
Exact Mass	367.03400
PSA	23.47000
LogP	4.51440

WGK Germany	3
HS Code	2933990090

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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