Synonym
SCH-23390; SCH23390; SCH 23390; SCH-23390 maleate;
IUPAC/Chemical Name
(R)-8-chloro-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol maleate
InChi Key
FGHVSEXHEAUJBT-HFNHQGOYSA-N
InChi Code
InChI=1S/C17H18ClNO.C4H4O4/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12;5-3(6)1-2-4(7)8/h2-6,9-10,15,20H,7-8,11H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m1./s1
SMILES Code
OC1=C(Cl)C=C2CCN(C)C[C@H](C3=CC=CC=C3)C2=C1.O=C(O)/C=C\C(O)=O
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
Biological target:
SCH 23390 maleate is a dopamine D1-like receptor antagonist with Kis of 0.2 nM and 0.3 nM for the D1 and D5 receptor, respectively. SCH 23390 maleate is a human 5-HT2C receptor agonist with a Ki of 9.3 nM. SCH 23390 maleate inhibits GIRK channels with an IC50 of 268 nM.
In vitro activity:
In this study, SCH 23390 was discovered to inhibit GIRK channels, independent of receptor activation. The inhibition is selective, affecting GIRK currents induced by somatostatin or D3 dopamine receptors. SCH 23390 can depolarize membrane potential and induce action potentials in cells.
Reference: Mol Pharmacol. 2002 Jul;62(1):119-26. https://pubmed.ncbi.nlm.nih.gov/12065762/
In vivo activity:
SCH 23390 may have use in addiction treatment research. In a saccharin seeking rat model, systemic SCH 23390 injections reduced saccharin seeking and reduced saccharin seeking persistence.
Reference: Appetite. 2016 Oct 1;105:8-13. https://pubmed.ncbi.nlm.nih.gov/27179937/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
403.86
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. Kuzhikandathil EV, Oxford GS. Classic D1 dopamine receptor antagonist R-(+)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (SCH23390) directly inhibits G protein-coupled inwardly rectifying potassium channels. Mol Pharmacol. 2002 Jul;62(1):119-26. doi: 10.1124/mol.62.1.119. PMID: 12065762.
2. Millan MJ, Newman-Tancredi A, Quentric Y, Cussac D. The "selective" dopamine D1 receptor antagonist, SCH23390, is a potent and high efficacy agonist at cloned human serotonin2C receptors. Psychopharmacology (Berl). 2001 Jun;156(1):58-62. doi: 10.1007/s002130100742. PMID: 11465634.
3. Japarin RA, Harun N, Hassan Z, Müller CP. The dopamine D1 receptor antagonist SCH-23390 blocks the acquisition, but not expression of mitragynine-induced conditioned place preference in rats. Behav Brain Res. 2023 Sep 13;453:114638. doi: 10.1016/j.bbr.2023.114638. Epub 2023 Aug 22. PMID: 37619769.
4. Aoyama K, Barnes J, Koerber J, Glueck E, Dorsey K, Eaton L, Grimm JW. Systemic injection of the DAD1 antagonist SCH 23390 reduces saccharin seeking in rats. Appetite. 2016 Oct 1;105:8-13. doi: 10.1016/j.appet.2016.05.008. Epub 2016 May 11. PMID: 27179937; PMCID: PMC4980176.
In vitro protocol:
1. Kuzhikandathil EV, Oxford GS. Classic D1 dopamine receptor antagonist R-(+)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (SCH23390) directly inhibits G protein-coupled inwardly rectifying potassium channels. Mol Pharmacol. 2002 Jul;62(1):119-26. doi: 10.1124/mol.62.1.119. PMID: 12065762.
2. Millan MJ, Newman-Tancredi A, Quentric Y, Cussac D. The "selective" dopamine D1 receptor antagonist, SCH23390, is a potent and high efficacy agonist at cloned human serotonin2C receptors. Psychopharmacology (Berl). 2001 Jun;156(1):58-62. doi: 10.1007/s002130100742. PMID: 11465634.
In vivo protocol:
1. Japarin RA, Harun N, Hassan Z, Müller CP. The dopamine D1 receptor antagonist SCH-23390 blocks the acquisition, but not expression of mitragynine-induced conditioned place preference in rats. Behav Brain Res. 2023 Sep 13;453:114638. doi: 10.1016/j.bbr.2023.114638. Epub 2023 Aug 22. PMID: 37619769.
2. Aoyama K, Barnes J, Koerber J, Glueck E, Dorsey K, Eaton L, Grimm JW. Systemic injection of the DAD1 antagonist SCH 23390 reduces saccharin seeking in rats. Appetite. 2016 Oct 1;105:8-13. doi: 10.1016/j.appet.2016.05.008. Epub 2016 May 11. PMID: 27179937; PMCID: PMC4980176.
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