MedKoo Cat#: 584919 | Name: Opc 4392

Description:

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

Opc 4392 is an agonist of presynaptic dopamine D(2) receptor.

Chemical Structure

Opc 4392
Opc 4392
CAS#111073-34-8

Theoretical Analysis

MedKoo Cat#: 584919

Name: Opc 4392

CAS#: 111073-34-8

Chemical Formula: C24H29N3O2

Exact Mass: 391.2260

Molecular Weight: 391.52

Elemental Analysis: C, 73.63; H, 7.47; N, 10.73; O, 8.17

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 #
No Data
Synonym
Opc 4392; Opc-4392; Opc4392
IUPAC/Chemical Name
2(1H)-Quinolinone, 7-(3-(4-(2,3-dimethylphenyl)-1-piperazinyl)propoxy)-
InChi Key
RRLWEQBPSAFVAS-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H29N3O2/c1-18-5-3-6-23(19(18)2)27-14-12-26(13-15-27)11-4-16-29-21-9-7-20-8-10-24(28)25-22(20)17-21/h3,5-10,17H,4,11-16H2,1-2H3,(H,25,28)
SMILES Code
O=C1NC2=C(C=CC(OCCCN3CCN(C4=CC=CC(C)=C4C)CC3)=C2)C=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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 391.52 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.

Recalculate based on batch purity %
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: Murasaki M, Miura S, Ishigooka J, Ishii Y, Takahashi A, Fukuyama Y. Phase 1 study of a new antipsychotic drug, OPC-4392. Prog Neuropsychopharmacol Biol Psychiatry. 1988;12(5):793-802. PubMed PMID: 2906159. 2: Yasuda Y, Kikuchi T, Suzuki S, Tsutsui M, Yamada K, Hiyama T. 7-[3-(4-[2,3-Dimethylphenyl]piperazinyl)propoxy]-2(1H)-quinolinone (OPC-4392), a presynaptic dopamine autoreceptor agonist and postsynaptic D2 receptor antagonist. Life Sci. 1988;42(20):1941-54. PubMed PMID: 3130534. 3: Kikuchi T, Tottori K, Uwahodo Y, Hirose T, Miwa T, Oshiro Y, Morita S. 7-(4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butyloxy)-3,4-dihydro-2(1H)-quinolinon e (OPC-14597), a new putative antipsychotic drug with both presynaptic dopamine autoreceptor agonistic activity and postsynaptic D2 receptor antagonistic activity. J Pharmacol Exp Ther. 1995 Jul;274(1):329-36. PubMed PMID: 7616416. 4: Duval F, Mokrani MC, Macher JP, Crocq MA, Castro JO, Bailey P, Lataste X. Neuroendocrine profile of SDZ HDC-912 and OPC-4392, two new atypical antipsychotic drugs, in schizophrenic patients. Psychopharmacology (Berl). 1993;110(1-2):177-80. PubMed PMID: 7870880. 5: Kiuchi K, Hirata Y, Minami M, Nagatsu T. Effect of 7-(3-[4-(2,3-dimethylphenyl)piperazinyl]propoxy)- 2(1H)-quinolinone (OPC-4392), a newly synthesized agonist for presynaptic dopamine D2 receptor, on tyrosine hydroxylation in rat striatal slices. Life Sci. 1988;42(3):343-9. PubMed PMID: 2892110. 6: Momiyama T, Sasa M, Takaori S. D-2 receptor-mediated inhibition by a substituted quinolinone derivative, 7-[3-(4-(2,3-dimethylphenyl)piperazinyl)propoxy]-2(1H)-quinolinone (OPC-4392), of dopaminergic neurons in the ventral tegmental area. Life Sci. 1990;47(9):761-9. PubMed PMID: 1977066. 7: Sasa M, Ohno Y, Takaori S. Presynaptic inhibition of excitatory input from the substantia nigra to caudate nucleus neurons by a substituted quinolinone derivative, 7-[3-(4-(2,3-dimethylphenyl)piperazinyl)propoxy]-2(1H)-quinolinone (OPC-4392). Life Sci. 1988;43(3):263-9. PubMed PMID: 3398698. 8: Lawler CP, Prioleau C, Lewis MM, Mak C, Jiang D, Schetz JA, Gonzalez AM, Sibley DR, Mailman RB. Interactions of the novel antipsychotic aripiprazole (OPC-14597) with dopamine and serotonin receptor subtypes. Neuropsychopharmacology. 1999 Jun;20(6):612-27. PubMed PMID: 10327430. 9: Gerbaldo H, Demisch L, Lehmann CO, Bochnik J. The effect of OPC-4392, a partial dopamine receptor agonist on negative symptoms: results of an open study. Pharmacopsychiatry. 1988 Nov;21(6):387-8. PubMed PMID: 2907646. 10: Tadori Y, Kitagawa H, Forbes RA, McQuade RD, Stark A, Kikuchi T. Differences in agonist/antagonist properties at human dopamine D(2) receptors between aripiprazole, bifeprunox and SDZ 208-912. Eur J Pharmacol. 2007 Nov 28;574(2-3):103-11. Epub 2007 Aug 10. PubMed PMID: 17692841. 11: Jordan S, Regardie K, Johnson JL, Chen R, Kambayashi J, McQuade R, Kitagawa H, Tadori Y, Kikuchi T. In vitro functional characteristics of dopamine D2 receptor partial agonists in second and third messenger-based assays of cloned human dopamine D2Long receptor signalling. J Psychopharmacol. 2007 Aug;21(6):620-7. Epub 2006 Nov 8. PubMed PMID: 17092971. 12: Benkert O, Müller-Siecheneder F, Wetzel H. Dopamine agonists in schizophrenia: a review. Eur Neuropsychopharmacol. 1995;5 Suppl:43-53. Review. PubMed PMID: 8775758. 13: Nakai S, Hirose T, Mori T, Stark A, Araki H, Kikuchi T. The effect of aripiprazole on prepulse inhibition of the startle response in normal and hyperdopaminergic states in rats. Int J Neurosci. 2008 Jan;118(1):39-57. PubMed PMID: 18041605. 14: Fujikawa M, Nagashima M, Inoue T, Yamada K, Furukawa T. Partial agonistic effects of OPC-14597, a potential antipsychotic agent, on yawning behavior in rats. Pharmacol Biochem Behav. 1996 Apr;53(4):903-9. PubMed PMID: 8801596. 15: Tadori Y, Forbes RA, McQuade RD, Kikuchi T. Characterization of aripiprazole partial agonist activity at human dopamine D3 receptors. Eur J Pharmacol. 2008 Nov 12;597(1-3):27-33. doi: 10.1016/j.ejphar.2008.09.008. Epub 2008 Sep 20. PubMed PMID: 18831971. 16: Natesan S, Reckless GE, Barlow KB, Nobrega JN, Kapur S. Partial agonists in schizophrenia--why some work and others do not: insights from preclinical animal models. Int J Neuropsychopharmacol. 2011 Oct;14(9):1165-78. doi: 10.1017/S1461145710001343. Epub 2010 Nov 19. PubMed PMID: 21087552. 17: Tadori Y, Miwa T, Tottori K, Burris KD, Stark A, Mori T, Kikuchi T. Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic. Eur J Pharmacol. 2005 May 16;515(1-3):10-9. PubMed PMID: 15894311. 18: Zhang X, Nakata Y, Kikuchi T, Segawa T. Interactions of 7-[3-(4-[2,3-dimethylphenyl]piperazinyl)-propoxy]-2(1H)-quinolinone binding in rat striatum: effects of lesions. Pharm Res. 1990 Mar;7(3):280-2. PubMed PMID: 1971105. 19: Tadori Y, Kikuchi T. [Pharmacology of antipsychotics at human dopamine D2 and D3 receptors]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2012 Feb;32(1):9-18. Review. Japanese. PubMed PMID: 22568121. 20: Jordan S, Johnson JL, Regardie K, Chen R, Koprivica V, Tadori Y, Kambayashi J, Kitagawa H, Kikuchi T. Dopamine D2 receptor partial agonists display differential or contrasting characteristics in membrane and cell-based assays of dopamine D2 receptor signaling. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Mar 30;31(2):348-56. Epub 2006 Oct 27. PubMed PMID: 17070976.