SKF-38393 HBr| SKF-38,393 | CAS# 62717-42-4 | dopamine D1 receptor agonist

SKF-38393 HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522581

CAS#: 62717-42-4 (HCl)

Description: SKF-38393, also known as (+/-)-SKF-38393, is a synthetic compound of the benzazepine chemical class which acts as a selective D1/D5 receptor partial agonist. It has stimulant and anorectic effects. SKF-38393 improves temporal order memory performance in maternally deprived rats. SKF-38393 reverses cocaine-conditioned place preference in mice. SKF-38393 induces GAP-43 expression and long-term potentiation in hippocampus in vivo.

Chemical Structure

SKF-38393 HCl

CAS# 62717-42-4 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522581
Name: SKF-38393 HCl
CAS#: 62717-42-4 (HCl)
Chemical Formula: C16H18ClNO2
Exact Mass: 0.00
Molecular Weight: 291.780
Elemental Analysis: C, 65.86; H, 6.22; Cl, 12.15; N, 4.80; O, 10.97

Price and Availability

Size	Price	Availability
200mg	USD 250	2 Weeks
500mg	USD 550
1g	USD 950
2g	USD 1650
5g	USD 3450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 67287-49-4 (free base) 62717-42-4 (HCl) 81702-42-3 (R-isomer HCl) 62751-59-1 (R-isomer) 20012-10-6 (HBr),

Synonym: SKF-38393; SKF 38393; SKF38393; SKF-38,393; SKF 38,393; SKF38,393; SKF-38393 Cl; SKF-38393 hydrochloride

IUPAC/Chemical Name: 1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol hydrochloride

InChi Key: YEWHJCLOUYPAOH-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H17NO2.ClH/c18-15-8-12-6-7-17-10-14(13(12)9-16(15)19)11-4-2-1-3-5-11;/h1-5,8-9,14,17-19H,6-7,10H2;1H

SMILES Code: OC1=C(O)C=C2C(C3=CC=CC=C3)CNCCC2=C1.[H]Cl

Appearance: Solid powder

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: To be determined

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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	SKF-38393 HBr is a partial agonist of the dopamine D1-like receptors D1 and D5 (Kis = 1 and ~0.5 nM, respectively). It less potently binds D2, D3, and D4 receptors (Kis = ~150, 5,000, and 1,000 nM, respectively).
In vitro activity:	This study implies that SKF-38393 selectively inhibited the growth of MCF-7 cells, highlighting its potential as a targeted therapeutic agent for this specific breast cancer cell line. After 1 day, various breast cancer cell lines were exposed to SKF-38393 for 2 days. The results indicated that SKF-38393 caused a significant decrease in proliferation of MCF-7 cells. The IC50 value was 0.1 +/- 0.03 microM. There was no significant effect on MDA-MB231 and MCF-10 cells. Reference: Anticancer Drugs. 1995 Jun;6(3):471-4. https://pubmed.ncbi.nlm.nih.gov/7670147/
In vivo activity:	SKF-38393 has neurotoxic effects on dopaminergic neurons by activating of the sustained ERK-Bad-Bax system. In a rat model of Parkinson's disease, SKF-38393 administration for 8 weeks induced phosphorylation of sustained ERK1/2 and Bad at Ser155 (BadSer155), and augmented Bax expression. However, SKF-38393 only increased Bad phosphorylation at Ser112 (BadSer112) when administered for 4 weeks. Reference: Behav Brain Res. 2019 Jul 23;367:166-175. https://pubmed.ncbi.nlm.nih.gov/30930179/

Preparing Stock Solutions

The following data is based on the product molecular weight 291.78 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. Ohta K, Kuno S, Mizuta I, Fujinami A, Matsui H, Ohta M. Effects of dopamine agonists bromocriptine, pergolide, cabergoline, and SKF-38393 on GDNF, NGF, and BDNF synthesis in cultured mouse astrocytes. Life Sci. 2003 Jun 20;73(5):617-26. doi: 10.1016/s0024-3205(03)00321-7. PMID: 12770616. 2. Johnson DE, Ochieng J, Evans SL. The growth inhibitory properties of a dopamine agonist (SKF 38393) on MCF-7 cells. Anticancer Drugs. 1995 Jun;6(3):471-4. doi: 10.1097/00001813-199506000-00017. PMID: 7670147. 3. Park HJ, Zhao TT, Park KH, Lee MK. Repeated treatments with the D1 dopamine receptor agonist SKF-38393 modulate cell viability via sustained ERK-Bad-Bax activation in dopaminergic neuronal cells. Behav Brain Res. 2019 Jul 23;367:166-175. doi: 10.1016/j.bbr.2019.03.035. Epub 2019 Mar 28. PMID: 30930179. 4. Moro H, Sato H, Ida I, Oshima A, Sakurai N, Shihara N, Horikawa Y, Mikuni M. Effects of SKF-38393, a dopamine D1 receptor agonist on expression of amphetamine-induced behavioral sensitization and expression of immediate early gene arc in prefrontal cortex of rats. Pharmacol Biochem Behav. 2007 May;87(1):56-64. doi: 10.1016/j.pbb.2007.03.020. Epub 2007 Apr 6. PMID: 17499349.
In vitro protocol:	1. Ohta K, Kuno S, Mizuta I, Fujinami A, Matsui H, Ohta M. Effects of dopamine agonists bromocriptine, pergolide, cabergoline, and SKF-38393 on GDNF, NGF, and BDNF synthesis in cultured mouse astrocytes. Life Sci. 2003 Jun 20;73(5):617-26. doi: 10.1016/s0024-3205(03)00321-7. PMID: 12770616. 2. Johnson DE, Ochieng J, Evans SL. The growth inhibitory properties of a dopamine agonist (SKF 38393) on MCF-7 cells. Anticancer Drugs. 1995 Jun;6(3):471-4. doi: 10.1097/00001813-199506000-00017. PMID: 7670147.
In vivo protocol:	1. Park HJ, Zhao TT, Park KH, Lee MK. Repeated treatments with the D1 dopamine receptor agonist SKF-38393 modulate cell viability via sustained ERK-Bad-Bax activation in dopaminergic neuronal cells. Behav Brain Res. 2019 Jul 23;367:166-175. doi: 10.1016/j.bbr.2019.03.035. Epub 2019 Mar 28. PMID: 30930179. 2. Moro H, Sato H, Ida I, Oshima A, Sakurai N, Shihara N, Horikawa Y, Mikuni M. Effects of SKF-38393, a dopamine D1 receptor agonist on expression of amphetamine-induced behavioral sensitization and expression of immediate early gene arc in prefrontal cortex of rats. Pharmacol Biochem Behav. 2007 May;87(1):56-64. doi: 10.1016/j.pbb.2007.03.020. Epub 2007 Apr 6. PMID: 17499349.

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1: Park HJ, Zhao TT, Park KH, Lee MK. Repeated treatments with the D(1) dopamine receptor agonist SKF-38393 modulate cell viability via sustained ERK-Bad-Bax activation in dopaminergic neuronal cells. Behav Brain Res. 2019 Jul 23;367:166-175. doi: 10.1016/j.bbr.2019.03.035. Epub 2019 Mar 28. PubMed PMID: 30930179.

2: Huang KC, Gopula B, Kuo TS, Chiang CW, Wu PY, Henschke JP, Wu HL. Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: formal synthesis of (S)-SKF 38393. Org Lett. 2013 Nov 15;15(22):5730-3. doi: 10.1021/ol4027599. Epub 2013 Oct 30. PubMed PMID: 24171673.

3: Lejeune S, Dourmap N, Martres MP, Giros B, Daugé V, Naudon L. The dopamine D1 receptor agonist SKF 38393 improves temporal order memory performance in maternally deprived rats. Neurobiol Learn Mem. 2013 Nov;106:268-73. doi: 10.1016/j.nlm.2013.10.005. Epub 2013 Oct 17. PubMed PMID: 24140426.

4: Sabioni P, D'Almeida V, Andersen ML, Andreatini R, Galduróz JC. SKF 38393 reverses cocaine-conditioned place preference in mice. Neurosci Lett. 2012 Apr 4;513(2):214-8. doi: 10.1016/j.neulet.2012.02.041. Epub 2012 Feb 22. PubMed PMID: 22387069.

5: Zarrindast MR, Honardar Z, Sanea F, Owji AA. SKF 38393 and SCH 23390 inhibit reuptake of serotonin by rat hypothalamic synaptosomes. Pharmacology. 2011;87(1-2):85-9. doi: 10.1159/000323232. Epub 2011 Jan 15. PubMed PMID: 21242715.

6: Chocyk A, Czyrak A, Wedzony K. Dopamine D1-like receptors agonist SKF 38393 increases cFOS expression in the paraventricular nucleus of the hypothalamus--impact of acute and chronic cocaine. J Physiol Pharmacol. 2008 Sep;59(3):425-40. PubMed PMID: 18953088.

7: Amico F, Spowart-Manning L, Anwyl R, Rowan MJ. Performance- and task-dependent effects of the dopamine D1/D5 receptor agonist SKF 38393 on learning and memory in the rat. Eur J Pharmacol. 2007 Dec 22;577(1-3):71-7. Epub 2007 Sep 11. PubMed PMID: 17900561.

8: Moro H, Sato H, Ida I, Oshima A, Sakurai N, Shihara N, Horikawa Y, Mikuni M. Effects of SKF-38393, a dopamine D1 receptor agonist on expression of amphetamine-induced behavioral sensitization and expression of immediate early gene arc in prefrontal cortex of rats. Pharmacol Biochem Behav. 2007 May;87(1):56-64. Epub 2007 Apr 6. PubMed PMID: 17499349.

9: Williams S, Mmbaga N, Chirwa S. Dopaminergic D1 receptor agonist SKF 38393 induces GAP-43 expression and long-term potentiation in hippocampus in vivo. Neurosci Lett. 2006 Jul 10;402(1-2):46-50. Epub 2006 May 3. PubMed PMID: 16675111.

10: Cooper SJ, Al-Naser HA. Dopaminergic control of food choice: contrasting effects of SKF 38393 and quinpirole on high-palatability food preference in the rat. Neuropharmacology. 2006 Jun;50(8):953-63. Epub 2006 Mar 20. PubMed PMID: 16549074.

11: Li GH, Guan BC, Li ZW. Effects of dopamine, SKF-38393 and R(-)-NPA on ATP-activated currents in rat DRG neurons. Can J Physiol Pharmacol. 2005 Mar;83(3):267-77. PubMed PMID: 15870841.

12: Venerosi A, Valanzano A, Puopolo M, Calamandrei G. Neurobehavioral effects of prenatal exposure to AZT: a preliminary investigation with the D1 receptor agonist SKF 38393 in mice. Neurotoxicol Teratol. 2005 Jan-Feb;27(1):169-73. PubMed PMID: 15681130.

13: Gleason SD, Witkin JM. Effects of dopamine D1 receptor full agonists in rats trained to discriminate SKF 38393. Behav Pharmacol. 2004 Feb;15(1):85-9. PubMed PMID: 15075630.

14: Marwaha A, Lokhandwala MF. Diminished natriuretic response to dopamine D1 receptor agonist, SKF-38393 in obese Zucker rats. Clin Exp Hypertens. 2003 Nov;25(8):509-15. PubMed PMID: 14649308.

15: Desai RI, Terry P, Katz JL. Comparison of the discriminative-stimulus effects of SKF 38393 with those of other dopamine receptor agonists. Behav Pharmacol. 2003 May;14(3):223-8. PubMed PMID: 12799524.

16: Ohta K, Kuno S, Mizuta I, Fujinami A, Matsui H, Ohta M. Effects of dopamine agonists bromocriptine, pergolide, cabergoline, and SKF-38393 on GDNF, NGF, and BDNF synthesis in cultured mouse astrocytes. Life Sci. 2003 Jun 20;73(5):617-26. PubMed PMID: 12770616.

17: Uzbay IT, Kayir H. Bromocriptine and quinpirole, but not 7-OH-DPAT or SKF 38393, potentiate the inhibitory effect of L-NAME on ethanol-induced locomotor activity in mice. Naunyn Schmiedebergs Arch Pharmacol. 2003 Apr;367(4):414-21. Epub 2003 Feb 21. PubMed PMID: 12690434.

18: Beck J, Biały M, Kostowski W. Effects of D(1) receptor agonist SKF 38393 on male rat sexual behavior and postcopulatory departure in the goal compartment-runway paradigm. Physiol Behav. 2002 May 1;76(1):91-7. PubMed PMID: 12175592.

19: Joel D, Avisar A, Doljansky J. Enhancement of excessive lever-pressing after post-training signal attenuation in rats by repeated administration of the D1 antagonist SCH 23390 or the D2 agonist quinpirole, but not the D1 agonist SKF 38393 or the D2 antagonist haloperidol. Behav Neurosci. 2001 Dec;115(6):1291-300. PubMed PMID: 11770060.

20: Muralikrishnan D, Ebadi M. SKF-38393, a dopamine receptor agonist, attenuates 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity. Brain Res. 2001 Feb 23;892(2):241-7. PubMed PMID: 11172770.

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SKF-38393 HCl featured