1187020-80-9

Basic information

• Product Name: lumateperone (Tosylate)
• Synonyms: lumateperone (Tosylate);ITI 007;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);Lumateperone(ITI-007)
• CAS NO: 1187020-80-9
• Molecular Formula: C₇H₈O₃S*C₂₄H₂₈FN₃O
• Molecular Weight: 565.6986432
• Mol File: 1187020-80-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: lumateperone (Tosylate)(CAS DataBase Reference)
• NIST Chemistry Reference: lumateperone (Tosylate)(1187020-80-9)
• EPA Substance Registry System: lumateperone (Tosylate)(1187020-80-9)

Safety Data

• Hazardous Substances Data: 1187020-80-9(Hazardous Substances Data)

Usage

Biochem/physiol Actions

Lumateperone tosylate (ITI-007) is an orally active, potent 5-HT2A antagonist, postsynaptic D2 antagonist, and serotonin transporter SERT inhibitor (Ki = 0.5, 32, 62 nM, respectively) with in vivo antipsychotic efficacy and no effect toward receptors associated with cognitive and metabolic side effects of antipsychotic drugs (e.g., H1, 5-HT2C, muscarinic). ITI-007 blocks DOI-induced headtwitch (ID50 = 0.09 mg/kg, po.) and D-AMPH-induced hyperlocomotion in mice (ID50 = 0.95 mg/kg, po.), while also acting as a partial agonist at presynaptic striatal D2 receptors.

Upstream product

• 313368-91-1 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone 
• 104-15-4 toluene-4-sulfonic acid 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 53374-52-0 1-nitroso-3-keto-1,2,3,4-tetrahydroquinoxaline 
• 313544-31-9 2-oxo-2,3,9,10-tetrahydro-1H,7H-pyrido-[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-8-carboxylic acid ethyl ester 
• 87973-61-3 1-amino-3-keto-1,2,3,4-tetrahydroquinoxaline 
• 50709-33-6 2-bromophenylhydrazine hydrochloride 
• 1059630-11-3 6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloric acid salt 
• 40862-32-6 1-iodo-3-(p-fluorophenylcarbonyl)propane 
• 313368-85-3 (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 1059630-08-8 (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 
• 2098497-32-4 (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate 

Relevant articles and documents

SUBSTITUTED HETEROCYCLE FUSED GAMMA-CARBOLINES SYNTHESIS

The present invention provides improved methods for the preparation of substituted heterocycle fused gamma-carbolines, intermediates useful in producing them and methods for producing such intermediates and such heterocycle fused gamma-carbolines.

NOVEL SALTS AND CRYSTALS

The disclosure provides a new, stable, pharmaceutically acceptable bis-tosylate salt form of 1-(4-fluoro-phenyl)-4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl)-butan-1-one, together with methods of making and using them, and pharmaceutical compositions comprising them.

Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders

We report the synthesis and structure-activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT2A and dopamine D2 receptors. This work has led to the discovery of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl) -1-(4-fluorophenyl)-butan-1-one 4-methylbenzenesulfonate (ITI-007), which is a potent 5-HT2A antagonist, postsynaptic D2 antagonist, and inhibitor of serotonin transporter. This multifunctional drug candidate is orally bioavailable and exhibits good antipsychotic efficacy in vivo. Currently, this investigational new drug is under clinical development for the treatment of neuropsychiatric and neurological disorders.