1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone 4-methylbenzenesulfonate (1:1)
[CAS# 1187020-80-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone 4-methylbenzenesulfonate (1:1)
• Synonyms: ITI 007
• Molecular Formula: C₂₄H₂₈FN₃O.C₇H₈O₃S
• Molecular Weight: 565.70
• CAS Registry Number: 1187020-80-9
• EC Number: 827-249-5
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.CN1CCN2[C@H]3CCN(C[C@H]3C4=C2C1=CC=C4)CCCC(=O)C5=CC=C(C=C5)F

Properties

• Solubility: 2 mg/mL (DMSO)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H336-H361f
• Safety Statements: P202-P261-P271-P280-P304+P340+P312-P308+P313

Discovery and Applications

1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone 4-methylbenzenesulfonate (1:1) is a complex small-molecule compound that has garnered significant attention in pharmaceutical research due to its structural novelty and potential therapeutic applications. This compound belongs to a class of heterocyclic quinoxaline derivatives that are known to exhibit a broad spectrum of biological activity, making them promising candidates for drug development.

The initial discovery of this compound stemmed from efforts to develop new therapeutic agents targeting central nervous system disorders. Researchers focused on modifying the quinoxaline core to improve selectivity and potency against specific receptor subtypes implicated in neurological diseases. The incorporation of the pyrido[3',4':4,5]pyrrolo moiety resulted in enhanced binding affinity and favorable pharmacokinetics, which are critical for achieving therapeutic efficacy.

The synthesis of this compound typically involves a multi-step process that begins with the construction of the quinoxaline scaffold. This is followed by the introduction of the pyrrolo moiety through cyclization reactions, leading to the formation of the fused ring system. The final steps involve the selective fluorination of the phenyl group and the attachment of the butanone side chain, culminating in the production of the tosylate salt form to improve solubility and stability.

In preclinical studies, 1-(4-fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone demonstrated potent activity in models of neurodegenerative diseases. Its ability to modulate neurotransmitter systems has been linked to potential benefits in treating conditions such as schizophrenia, depression, and cognitive deficits. Additionally, its unique mechanism of action distinguishes it from existing treatments, offering the potential for improved patient outcomes and reduced side effects.

Clinical trials are underway to evaluate the safety, efficacy, and tolerability of this compound in human subjects. Preliminary results suggest promising pharmacological activity and a favorable safety profile, positioning it as a candidate for further development.

References

2024. Efficacy and safety of lumateperone for bipolar depression and schizophrenia: a systematic review and meta-analysis. The international journal of neuropsychopharmacology.
DOI: 10.1093/ijnp/pyae052

2021. A review of the pharmacology and clinical profile of lumateperone for the treatment of schizophrenia. Advances in pharmacology (San Diego, Calif.).
DOI: 10.1016/bs.apha.2020.09.001

2014. Discovery of a Tetracyclic Quinoxaline Derivative as a Potent and Orally Active Multifunctional Drug Candidate for the Treatment of Neuropsychiatric and Neurological Disorders. Journal of Medicinal Chemistry.
DOI: 10.1021/jm401958n