SKF-38393 free base| CAS# 62717-42-4

MedKoo Cat#: 531300 | Name: SKF-38393 free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SKF-38393, aslo 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 free base

CAS#67287-49-4 (free base)

Theoretical Analysis

MedKoo Cat#: 531300

Name: SKF-38393 free base

CAS#: 67287-49-4 (free base)

Chemical Formula: C16H17NO2

Exact Mass: 255.1259

Molecular Weight: 255.32

Elemental Analysis: C, 75.27; H, 6.71; N, 5.49; O, 12.53

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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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

SKF38393; SKF-38393; SKF 38393; SKF38393 free base

IUPAC/Chemical Name

(±)-1-Phenyl-2,3,4,5-tetrahydro-(1H)-3-benzazepine-7,8-diol

InChi Key

JUDKOGFHZYMDMF-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H17NO2/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

SMILES Code

OC1=C(O)C=C2C(C3=CC=CC=C3)CNCCC2=C1

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

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 255.32 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

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.