Related CAS #
67287-95-0(SKF-83959 HBr)
Synonym
SKF-83959 HBr; SKF-83959; SKF83959; SKF 83959.
IUPAC/Chemical Name
6-Chloro-2,3,4,5-tetrahydro-3-methyl-1-(3-methylphenyl)-1H-3-benzazepine-7,8-diol Hydrobromide
InChi Key
FHYWNBUFNGHNCP-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H20ClNO2.BrH/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19;/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3;1H
SMILES Code
OC1=C(O)C=C2C(C3=CC=CC(C)=C3)CN(C)CCC2=C1Cl.[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
>2 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-83959 HBr is a dopamine D1-like receptor partial agonist (Ki values are 1.18, 7.56, 920 and 399 nM for rat D1, D5, D2 and D3 receptors respectively). SKF-83959 HBr has been shown to potentiate agonist binding of the σ1 receptor.
In vitro activity:
This pharmacological characterization study demonstrates that SKF-83959 is not a highly-biased, functionally selective D1 ligand. Its reported behavioral effects are attributed to its partial D1 agonism in conventional signaling pathways, resembling the well-known partial agonist SKF38393. SKF-83959 exhibits partial agonism (not antagonism) at adenylate cyclase and D1-mediated β-arrestin recruitment, but does not affect phospholipase C signaling in heterologous systems.
Reference: Neuropharmacology. 2014 Nov;86:145-54. https://pubmed.ncbi.nlm.nih.gov/24929112/
In vivo activity:
This study indicates that SKF-83959 might have complex effects on the brain and that its specific mechanisms and potential applications in cognitive disorders must be further investigated. In a rat model of schizophrenia, repeated SKF-83959 treatment increased signal amplitude and enhanced the spectral power of low frequency delta and theta oscillations in the hippocampus. In MAM rats, SKF-83959 inhibited spatial learning and induced a significant increase in thigmotactic behaviour.
Reference: Eur J Neurosci. 2017 Aug;46(4):2015-2025. https://pubmed.ncbi.nlm.nih.gov/28677227/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
15.9 |
50.00 |
|
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
398.73
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. Lee SM, Kant A, Blake D, Murthy V, Boyd K, Wyrick SJ, Mailman RB. SKF-83959 is not a highly-biased functionally selective D1 dopamine receptor ligand with activity at phospholipase C. Neuropharmacology. 2014 Nov;86:145-54. doi: 10.1016/j.neuropharm.2014.05.042. Epub 2014 Jun 12. PMID: 24929112; PMCID: PMC4188748.
2. Andringa G, Drukarch B, Leysen JE, Cools AR, Stoof JC. The alleged dopamine D1 receptor agonist SKF 83959 is a dopamine D1 receptor antagonist in primate cells and interacts with other receptors. Eur J Pharmacol. 1999 Jan 1;364(1):33-41. doi: 10.1016/s0014-2999(98)00825-5. PMID: 9920182.
3. Perreault ML, Fan T, Banasikowski TJ, Grace AA, George SR. The atypical dopamine receptor agonist SKF 83959 enhances hippocampal and prefrontal cortical neuronal network activity in a rat model of cognitive dysfunction. Eur J Neurosci. 2017 Aug;46(4):2015-2025. doi: 10.1111/ejn.13635. Epub 2017 Aug 1. PMID: 28677227.
4. Tomiyama K, Song L, Kobayashi M, Kinsella A, Kanematsu T, Hirata M, Koshikawa N, Waddington JL. Orofacial movements in phospholipase C-related catalytically inactive protein-1/2 double knockout mice: Effect of the GABAergic agent diazepam and the D(1) dopamine receptor agonist SKF 83959. Synapse. 2010 Sep;64(9):714-20. doi: 10.1002/syn.20798. PMID: 20340178.
In vitro protocol:
1. Lee SM, Kant A, Blake D, Murthy V, Boyd K, Wyrick SJ, Mailman RB. SKF-83959 is not a highly-biased functionally selective D1 dopamine receptor ligand with activity at phospholipase C. Neuropharmacology. 2014 Nov;86:145-54. doi: 10.1016/j.neuropharm.2014.05.042. Epub 2014 Jun 12. PMID: 24929112; PMCID: PMC4188748.
2. Andringa G, Drukarch B, Leysen JE, Cools AR, Stoof JC. The alleged dopamine D1 receptor agonist SKF 83959 is a dopamine D1 receptor antagonist in primate cells and interacts with other receptors. Eur J Pharmacol. 1999 Jan 1;364(1):33-41. doi: 10.1016/s0014-2999(98)00825-5. PMID: 9920182.
In vivo protocol:
1. Perreault ML, Fan T, Banasikowski TJ, Grace AA, George SR. The atypical dopamine receptor agonist SKF 83959 enhances hippocampal and prefrontal cortical neuronal network activity in a rat model of cognitive dysfunction. Eur J Neurosci. 2017 Aug;46(4):2015-2025. doi: 10.1111/ejn.13635. Epub 2017 Aug 1. PMID: 28677227.
2. Tomiyama K, Song L, Kobayashi M, Kinsella A, Kanematsu T, Hirata M, Koshikawa N, Waddington JL. Orofacial movements in phospholipase C-related catalytically inactive protein-1/2 double knockout mice: Effect of the GABAergic agent diazepam and the D(1) dopamine receptor agonist SKF 83959. Synapse. 2010 Sep;64(9):714-20. doi: 10.1002/syn.20798. PMID: 20340178.
1: Lee SM, Kant A, Blake D, Murthy V, Boyd K, Wyrick SJ, Mailman RB. SKF-83959 is not a highly-biased functionally selective D1 dopamine receptor ligand with activity at phospholipase C. Neuropharmacology. 2014 Nov;86:145-54. doi: 10.1016/j.neuropharm.2014.05.042. Epub 2014 Jun 12. PubMed PMID: 24929112; PubMed Central PMCID: PMC4188748.
2: Tomiyama K, Song L, Kobayashi M, Kinsella A, Kanematsu T, Hirata M, Koshikawa N, Waddington JL. Orofacial movements in phospholipase C-related catalytically inactive protein-1/2 double knockout mice: Effect of the GABAergic agent diazepam and the D(1) dopamine receptor agonist SKF 83959. Synapse. 2010 Sep;64(9):714-20. doi: 10.1002/syn.20798. PubMed PMID: 20340178.
3: Fujita S, Kiguchi M, Kobayashi M, Kinsella A, Koshikawa N, Waddington JL. Assessment of jaw movements by magnetic sensor in relation to topographies of orofacial behaviour in freely moving rats: Studies with the dopamine D(1)-like receptor agonists SKF 83822 vs SKF 83959. Eur J Pharmacol. 2010 Apr 25;632(1-3):39-44. doi: 10.1016/j.ejphar.2010.01.018. Epub 2010 Feb 1. PubMed PMID: 20122923.
4: Desai RI, Neumeyer JL, Paronis CA, Nguyen P, Bergman J. Behavioral effects of the R-(+)- and S-(-)-enantiomers of the dopamine D(1)-like partial receptor agonist SKF 83959 in monkeys. Eur J Pharmacol. 2007 Mar 8;558(1-3):98-106. Epub 2006 Dec 1. Erratum in: Eur J Pharmacol. 2007 Dec 1;575(1-3):187. PubMed PMID: 17207791; PubMed Central PMCID: PMC2447824.
5: Wirtshafter D, Osborn CV. The atypical dopamine D1 receptor agonist SKF 83959 induces striatal Fos expression in rats. Eur J Pharmacol. 2005 Dec 28;528(1-3):88-94. Epub 2005 Dec 1. PubMed PMID: 16324697.
6: Cools AR, Lubbers L, van Oosten RV, Andringa G. SKF 83959 is an antagonist of dopamine D1-like receptors in the prefrontal cortex and nucleus accumbens: a key to its antiparkinsonian effect in animals? Neuropharmacology. 2002 Feb;42(2):237-45. PubMed PMID: 11804620.
7: Platt DM, Rowlett JK, Spealman RD. Dissociation of cocaine-antagonist properties and motoric effects of the D1 receptor partial agonists SKF 83959 and SKF 77434. J Pharmacol Exp Ther. 2000 Jun;293(3):1017-26. PubMed PMID: 10869406.
8: Andringa G, Stoof JC, Cools AR. Sub-chronic administration of the dopamine D(1) antagonist SKF 83959 in bilaterally MPTP-treated rhesus monkeys: stable therapeutic effects and wearing-off dyskinesia. Psychopharmacology (Berl). 1999 Oct;146(3):328-34. PubMed PMID: 10541734.
9: Andringa G, Drukarch B, Leysen JE, Cools AR, Stoof JC. The alleged dopamine D1 receptor agonist SKF 83959 is a dopamine D1 receptor antagonist in primate cells and interacts with other receptors. Eur J Pharmacol. 1999 Jan 1;364(1):33-41. PubMed PMID: 9920182.
