Synonym
SKF 83566 hydrobromide, SKF83566 hydrobromide, SKF-83566 hydrobromide, SKF 83566 HBr, SKF83566 HBr, SKF-83566 HBr
IUPAC/Chemical Name
8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol, monohydrobromide
InChi Key
SDQJYYGODYRPBR-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H18BrNO.BrH/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;1H
SMILES Code
OC1=C(Br)C=C2CCN(C)CC(C3=CC=CC=C3)C2=C1.[H]Br
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
SKF-83566 HBr is a D1DR antagonist and an antagonist at the vascular 5-HT2 receptor (Ki=11 nM). SKF-83566 competively inhibits DAT 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.
In vitro activity:
SKF-83566 could potentially mitigate cocaine effects in vivo due to its higher potency at the cocaine binding site compared to the dopamine binding site of the DAT. This study confirmed that SKF-83566 is a competitive DAT inhibitor with an IC50 of 5.7 μM. Binding studies with [(3)H]CFT, a cocaine analog, showed even more potent action of SKF-83566 at the DAT cocaine binding site (IC50 = 0.51 μM).
Reference: J Neurochem. 2011 Sep;118(5):714-20. https://pubmed.ncbi.nlm.nih.gov/21689106/
In vivo activity:
SKF 83566 has potential in morphine withdrawal syndrome treatment. In mice, when administered alone, SKF 83566 produced inhibitory effects on naloxone-induced morphine withdrawal symptoms. Pretreatment with SKF 83566 reinforced the inhibitory action of higher doses of bromocriptine. Also, pretreatment with sulpiride and SKF 83566 markedly decreased the potentiating effects of
l-dopa and bromocriptine, reinforcing the inhibitory action of bromocriptine on naloxone-induced morphine withdrawal syndrome.
Reference: Hum Psychopharmacol. 2000 Mar;15(2):95-101. https://pubmed.ncbi.nlm.nih.gov/12404338/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
41.3 |
100.00 |
|
| Ethanol |
10.3 |
25.00 |
|
| Water |
2.1 |
5.00 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.15
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Cheng F, Twardowski L, Fehr S, Aner C, Schaeffeler E, Joos T, Knorpp T, Dorweiler B, Laufer S, Schwab M, Torzewski M. Selective p38α MAP kinase/MAPK14 inhibition in enzymatically modified LDL-stimulated human monocytes: implications for atherosclerosis. FASEB J. 2017 Feb;31(2):674-686. doi: 10.1096/fj.201600669R. Epub 2016 Nov 8. PMID: 27871059.
2. Stouffer MA, Ali S, Reith ME, Patel JC, Sarti F, Carr KD, Rice ME. SKF-83566, a D1-dopamine receptor antagonist, inhibits the dopamine transporter. J Neurochem. 2011 Sep;118(5):714-20. doi: 10.1111/j.1471-4159.2011.07357.x. Epub 2011 Jul 21. PMID: 21689106; PMCID: PMC3337772.
3. Jacoby SM, Currie PJ. SKF 83566 attenuates the effects of ghrelin on performance in the object location memory task. Neurosci Lett. 2011 Oct 31;504(3):316-20. doi: 10.1016/j.neulet.2011.09.056. Epub 2011 Oct 1. PMID: 21982806.
4. Samini M, Fakhrian R, Mohagheghi M, Dehpour AR. Comparison of the effect of levodopa and bromocriptine on naloxone-precipitated morphine withdrawal symptoms in mice. Hum Psychopharmacol. 2000 Mar;15(2):95-101. doi: 10.1002/(SICI)1099-1077(200003)15:2<95::AID-HUP148>3.0.CO;2-A. PMID: 12404338.
In vitro protocol:
1. Cheng F, Twardowski L, Fehr S, Aner C, Schaeffeler E, Joos T, Knorpp T, Dorweiler B, Laufer S, Schwab M, Torzewski M. Selective p38α MAP kinase/MAPK14 inhibition in enzymatically modified LDL-stimulated human monocytes: implications for atherosclerosis. FASEB J. 2017 Feb;31(2):674-686. doi: 10.1096/fj.201600669R. Epub 2016 Nov 8. PMID: 27871059.
2. Stouffer MA, Ali S, Reith ME, Patel JC, Sarti F, Carr KD, Rice ME. SKF-83566, a D1-dopamine receptor antagonist, inhibits the dopamine transporter. J Neurochem. 2011 Sep;118(5):714-20. doi: 10.1111/j.1471-4159.2011.07357.x. Epub 2011 Jul 21. PMID: 21689106; PMCID: PMC3337772.
In vivo protocol:
1. Jacoby SM, Currie PJ. SKF 83566 attenuates the effects of ghrelin on performance in the object location memory task. Neurosci Lett. 2011 Oct 31;504(3):316-20. doi: 10.1016/j.neulet.2011.09.056. Epub 2011 Oct 1. PMID: 21982806.
2. Samini M, Fakhrian R, Mohagheghi M, Dehpour AR. Comparison of the effect of levodopa and bromocriptine on naloxone-precipitated morphine withdrawal symptoms in mice. Hum Psychopharmacol. 2000 Mar;15(2):95-101. doi: 10.1002/(SICI)1099-1077(200003)15:2<95::AID-HUP148>3.0.CO;2-A. PMID: 12404338.
1: Pinheiro T, Otrocka M, Seashore-Ludlow B, Rraklli V, Holmberg J, Forsberg- Nilsson K, Simon A, Kirkham M. Reprint of: A chemical screen identifies trifluoperazine as an inhibitor of glioblastoma growth. Biochem Biophys Res Commun. 2018 May 5;499(2):136-142. doi: 10.1016/j.bbrc.2018.03.001. Epub 2018 Mar 23. PMID: 29580626.
2: Pinheiro T, Otrocka M, Seashore-Ludlow B, Rraklli V, Holmberg J, Forsberg- Nilsson K, Simon A, Kirkham M. A chemical screen identifies trifluoperazine as an inhibitor of glioblastoma growth. Biochem Biophys Res Commun. 2017 Dec 16;494(3-4):477-483. doi: 10.1016/j.bbrc.2017.10.106. Epub 2017 Oct 21. PMID: 29066348.
3: Witkin JM, Newman AH, Nowak G, Katz JL. Role of dopamine D1 receptors in the lethal effects of cocaine and a quaternary methiodide analog. J Pharmacol Exp Ther. 1993 Oct;267(1):266-74. PMID: 7901394.
4: Ono H, Ito H, Fukuda H. 2-phenylethylamine and methamphetamine enhance the spinal monosynaptic reflex by releasing noradrenaline from the terminals of descending fibers. Jpn J Pharmacol. 1991 Mar;55(3):359-66. doi: 10.1254/jjp.55.359. PMID: 1830350.
5: Capasso A, Carginale V, Madonna L, Mancaniello D, Scudiero R, Paolo De Prisco P, De Petrocellis B, Parisi E. A dopamine- and octopamine-sensitive adenylate cyclase in the nervous system of Octopus vulgaris. Comp Biochem Physiol B. 1991;100(4):805-8. doi: 10.1016/0305-0491(91)90294-n. PMID: 1782763.
