Synonym
SKF-81297 HBr; SKF-81297; SKF 81297; SKF81297;
IUPAC/Chemical Name
6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
InChi Key
GHWJEDJMOVUXEC-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16ClNO2/c17-15-11-6-7-18-9-13(10-4-2-1-3-5-10)12(11)8-14(19)16(15)20/h1-5,8,13,18-20H,6-7,9H2
SMILES Code
OC1=C(O)C=C2C(C3=CC=CC=C3)CNCCC2=C1Cl
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, DMF, and ethanol
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
2934.99.03.00
Biological target:
SKF-81297 is a selective agonist of the dopamine D1-like receptor (Ki = 1.9 nM). It demonstrates comparatively lower binding affinity for the dopamine D2, dopamine D3, serotonin 5-HT2A, and adrenergic α2 receptors (Kis = 1,272, >10,000, 955, and 509 nM, respectively).
In vitro activity:
This study suggests that dopamine D1R activation and ensuing cAMP production dynamically regulates the efficiency and timing of IP(3)-mediated intracellular Ca(2+) store mobilization. In D1HEK293 cells, SKF 81297 evoked a robust dose-dependent increase in Ca(2+)(i) following 'priming' of endogenous G(q/11)-coupled muscarinic or purinergic receptors. In neurons, SKF81297 and SKF83959 promoted Ca(2+) oscillations in response to G(q/11)-coupled metabotropic glutamate receptor (mGluR) stimulation.
Reference: Neurosignals. 2008;16(2-3):112-23. https://pubmed.ncbi.nlm.nih.gov/18253052/
In vivo activity:
Chronic systemic administration of SKF-81297 alters glutamic acid decarboxylase (GAD) mRNA levels in striatonigral neurons in rats with a unilateral 6-OHDA lesion. After a single injection of SKF-81297, striatal GAD65 mRNA levels were significantly increased at 3 but not 72 h. In contrast, striatal GAD67 mRNA levels were increased and nigral alpha1 mRNA levels were decreased at 72 but not 3 h. The results suggest that different signaling pathways are involved in the modulation by dopamine D1/D5 receptors of GAD65 and GAD67 mRNA levels in striatonigral neurons.
Reference: Neuroscience. 2008 Jun 26;154(3):1088-99. https://pubmed.ncbi.nlm.nih.gov/18495353/
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Solvent |
mg/mL |
mM |
comments |
| Solubility |
| To be determined |
0.0 |
0.00 |
|
|
0.0 |
0.00 |
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|
0.0 |
0.00 |
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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
289.76
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. Guha S, Baltazar GC, Tu LA, Liu J, Lim JC, Lu W, Argall A, Boesze-Battaglia K, Laties AM, Mitchell CH. Stimulation of the D5 dopamine receptor acidifies the lysosomal pH of retinal pigmented epithelial cells and decreases accumulation of autofluorescent photoreceptor debris. J Neurochem. 2012 Aug;122(4):823-33. doi: 10.1111/j.1471-4159.2012.07804.x. Epub 2012 Jun 27. PMID: 22639870; PMCID: PMC3408960.
2. Dai R, Ali MK, Lezcano N, Bergson C. A crucial role for cAMP and protein kinase A in D1 dopamine receptor regulated intracellular calcium transients. Neurosignals. 2008;16(2-3):112-23. doi: 10.1159/000111557. Epub 2008 Feb 5. PMID: 18253052.
3. Yamamoto N, Soghomonian JJ. Time-course of SKF-81297-induced increase in glutamic acid decarboxylase 65 and 67 mRNA levels in striatonigral neurons and decrease in GABA(A) receptor alpha1 subunit mRNA levels in the substantia nigra, pars reticulata, in adult rats with a unilateral 6-hydroxydopamine lesion. Neuroscience. 2008 Jun 26;154(3):1088-99. doi: 10.1016/j.neuroscience.2008.04.015. Epub 2008 Apr 16. PMID: 18495353; PMCID: PMC2483836.
4. Chausmer AL, Katz JL. Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents. Psychopharmacology (Berl). 2002 Jan;159(2):145-53. doi: 10.1007/s002130100896. Epub 2001 Sep 22. PMID: 11862342.
In vitro protocol:
1. Guha S, Baltazar GC, Tu LA, Liu J, Lim JC, Lu W, Argall A, Boesze-Battaglia K, Laties AM, Mitchell CH. Stimulation of the D5 dopamine receptor acidifies the lysosomal pH of retinal pigmented epithelial cells and decreases accumulation of autofluorescent photoreceptor debris. J Neurochem. 2012 Aug;122(4):823-33. doi: 10.1111/j.1471-4159.2012.07804.x. Epub 2012 Jun 27. PMID: 22639870; PMCID: PMC3408960.
2. Dai R, Ali MK, Lezcano N, Bergson C. A crucial role for cAMP and protein kinase A in D1 dopamine receptor regulated intracellular calcium transients. Neurosignals. 2008;16(2-3):112-23. doi: 10.1159/000111557. Epub 2008 Feb 5. PMID: 18253052.
In vivo protocol:
1. Yamamoto N, Soghomonian JJ. Time-course of SKF-81297-induced increase in glutamic acid decarboxylase 65 and 67 mRNA levels in striatonigral neurons and decrease in GABA(A) receptor alpha1 subunit mRNA levels in the substantia nigra, pars reticulata, in adult rats with a unilateral 6-hydroxydopamine lesion. Neuroscience. 2008 Jun 26;154(3):1088-99. doi: 10.1016/j.neuroscience.2008.04.015. Epub 2008 Apr 16. PMID: 18495353; PMCID: PMC2483836.
2. Chausmer AL, Katz JL. Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents. Psychopharmacology (Berl). 2002 Jan;159(2):145-53. doi: 10.1007/s002130100896. Epub 2001 Sep 22. PMID: 11862342.
1: Yamamoto N, Soghomonian JJ. Time-course of SKF-81297-induced increase in glutamic acid decarboxylase 65 and 67 mRNA levels in striatonigral neurons and decrease in GABA(A) receptor alpha1 subunit mRNA levels in the substantia nigra, pars reticulata, in adult rats with a unilateral 6-hydroxydopamine lesion. Neuroscience. 2008 Jun 26;154(3):1088-99. doi: 10.1016/j.neuroscience.2008.04.015. Epub 2008 Apr 16. PubMed PMID: 18495353; PubMed Central PMCID: PMC2483836.
2: Schwartz RA, Greenwald ER, Fletcher PJ, Houle S, DaSilva JN. Up-regulated dopamine D1 receptor binding can be detected in vivo following repeated SCH 23390, but not SKF 81297 or 6-hydroxydopamine, treatments. Eur J Pharmacol. 2003 Jan 17;459(2-3):195-201. PubMed PMID: 12524146.
3: Chausmer AL, Katz JL. Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents. Psychopharmacology (Berl). 2002 Jan;159(2):145-53. Epub 2001 Sep 22. PubMed PMID: 11862342.
4: Andringa G, Vermeulen RJ, Drukarch B, Renier WO, Stoof JC, Cools AR. The validity of the pretreated, unilaterally MPTP-treated monkeys as a model of Parkinson's disease: a detailed behavioural analysis of the therapeutic and undesired effects of the D2 agonist quinpirole and the D1 agonist SKF 81297. Behav Pharmacol. 1999 Mar;10(2):163-73. PubMed PMID: 10780829.
5: Abrahams BS, Rutherford JD, Mallet PE, Beninger RJ. Place conditioning with the dopamine D1-like receptor agonist SKF 82958 but not SKF 81297 or SKF 77434. Eur J Pharmacol. 1998 Feb 19;343(2-3):111-8. PubMed PMID: 9570457.
6: Vermeulen RJ, Drukarch B, Sahadat MC, Goosen C, Wolters EC, Stoof JC. The dopamine D1 agonist SKF 81297 and the dopamine D2 agonist LY 171555 act synergistically to stimulate motor behavior of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned parkinsonian rhesus monkeys. Mov Disord. 1994 Nov;9(6):664-72. PubMed PMID: 7845408.
7: Rosenzweig-Lipson S, Bergman J. Dopamine D1 receptor involvement in the discriminative-stimulus effects of SKF 81297 in squirrel monkeys. J Pharmacol Exp Ther. 1993 Nov;267(2):765-75. PubMed PMID: 7902432.
8: Vermeulen RJ, Drukarch B, Sahadat MC, Goosen C, Wolters EC, Stoof JC. The selective dopamine D1 receptor agonist, SKF 81297, stimulates motor behaviour of MPTP-lesioned monkeys. Eur J Pharmacol. 1993 Apr 22;235(1):143-7. PubMed PMID: 8100193.
9: Reavill C, B Bond, Overend P, Hunter AJ. Pharmacological characterization of the discriminative stimulus properties of the dopamine D1 agonist, SKF 81297. Behav Pharmacol. 1993 Apr;4(2):135-146. PubMed PMID: 11224180.
10: Weed MR, Vanover KE, Woolverton WL. Reinforcing effect of the D1 dopamine agonist SKF 81297 in rhesus monkeys. Psychopharmacology (Berl). 1993;113(1):51-2. PubMed PMID: 7862828.
