Related CAS #
260369-93-5 (mesylate); 145969-30-8(free base)
Synonym
OPC-14523; VPI-013; OPC14523; VPI013; OPC 14523; VPI 013
IUPAC/Chemical Name
1-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-5-methoxy-3,4-dihydroquinolin-2(1H)-one
InChi Key
TZZGTNZBLPCBIS-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H28ClN3O2/c1-29-22-8-3-7-21-20(22)9-10-23(28)27(21)12-4-11-25-13-15-26(16-14-25)19-6-2-5-18(24)17-19/h2-3,5-8,17H,4,9-16H2,1H3
SMILES Code
O=C1N(CCCN2CCN(C3=CC=CC(Cl)=C3)CC2)C4=C(C(OC)=CC=C4)CC1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.94
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: Jordan S, Chen R, Koprivica V, Hamilton R, Whitehead RE, Tottori K, Kikuchi T. In vitro profile of the antidepressant candidate OPC-14523 at rat and human 5-HT1A receptors. Eur J Pharmacol. 2005 Jul 11;517(3):165-73. PubMed PMID: 15985260.
2: Bermack JE, Debonnel G. Effects of OPC-14523, a combined sigma and 5-HT1a ligand, on pre- and post-synaptic 5-HT1a receptors. J Psychopharmacol. 2007 Jan;21(1):85-92. PubMed PMID: 16533864.
3: Tottori K, Nakai M, Uwahodo Y, Miwa T, Yamada S, Oshiro Y, Kikuchi T, Altar CA. Attenuation of scopolamine-induced and age-associated memory impairments by the sigma and 5-hydroxytryptamine(1A) receptor agonist OPC-14523 (1-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-methoxy-3,4-dihydro-2[1H]-quino linone monomethanesulfonate). J Pharmacol Exp Ther. 2002 Apr;301(1):249-57. PubMed PMID: 11907181.
4: Tottori K, Miwa T, Uwahodo Y, Yamada S, Nakai M, Oshiro Y, Kikuchi T, Altar CA. Antidepressant-like responses to the combined sigma and 5-HT1A receptor agonist OPC-14523. Neuropharmacology. 2001 Dec;41(8):976-88. PubMed PMID: 11747902.
5: Bermack JE, Haddjeri N, Debonnel G. Effects of the potential antidepressant OPC-14523 [1-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-methoxy-3,4-dihydro-2-quinolino ne monomethanesulfonate] a combined sigma and 5-HT1A ligand: modulation of neuronal activity in the dorsal raphe nucleus. J Pharmacol Exp Ther. 2004 Aug;310(2):578-83. PubMed PMID: 15044555.
6: Skuza G, Wedzony K. Behavioral pharmacology of sigma-ligands. Pharmacopsychiatry. 2004 Nov;37 Suppl 3:S183-8. Review. PubMed PMID: 15547784.
7: Skuza G. Potential antidepressant activity of sigma ligands. Pol J Pharmacol. 2003 Nov-Dec;55(6):923-34. Review. PubMed PMID: 14730086.
8: Oshiro Y, Sakurai Y, Sato S, Kurahashi N, Tanaka T, Kikuchi T, Tottori K, Uwahodo Y, Miwa T, Nishi T. 3,4-dihydro-2(1H)-quinolinone as a novel antidepressant drug: synthesis and pharmacology of 1-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-3,4- dihydro-5-methoxy-2(1H)-quinolinone and its derivatives. J Med Chem. 2000 Jan 27;43(2):177-89. PubMed PMID: 10649973.
