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SML2866

Sigma-Aldrich

Lumateperone tosylate

≥98% (HPLC)

Synonym(s):

1-(4-Fluorophenyl)-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]butan-1-one 4-methylbenzenesulfonate, 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

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About This Item

Empirical Formula (Hill Notation):
C24H28FN3O · C7H8O3S
CAS Number:
1187020-80-9
Molecular Weight:
565.70
MDL number:
MFCD29922434
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -10 to -14, c = 1 in DMSO

color

white to very dark gray

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(C1=CC=C(F)C=C1)CCCN2CC[C@]([C@@]3([H])C2)([H])N4CCN(C)C5=C4C3=CC=C5.O=S(C6=CC=C(C)C=C6)(O)=O

InChI

1S/C24H28FN3O.C7H8O3S/c1-26-14-15-28-21-11-13-27(16-20(21)19-4-2-5-22(26)24(19)28)12-3-6-23(29)17-7-9-18(25)10-8-17;1-6-2-4-7(5-3-6)11(8,9)10/h2,4-5,7-10,20-21H,3,6,11-16H2,1H3;2-5H,1H3,(H,8,9,10)/t20-,21-;/m0./s1

InChI key

LHAPOGAFBLSJJQ-GUTACTQSSA-N

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H336,H361f

Hazard Classifications

Repr. 2 - STOT SE 3

Target Organs

Central nervous system

WGK

WGK 3

Regulatory Information

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Robert E Davis et al.
Psychopharmacology, 232(15), 2863-2872 (2015-04-07)
Central modulation of serotonin and dopamine underlies efficacy for a variety of psychiatric therapeutics. ITI-007 is an investigational new drug in development for treatment of schizophrenia, mood disorders, and other neuropsychiatric disorders. The purpose of this study was to determine
Gretchen L Snyder et al.
Psychopharmacology, 232(3), 605-621 (2014-08-15)
Schizophrenia remains among the most prevalent neuropsychiatric disorders, and current treatment options are accompanied by unwanted side effects. New treatments that better address core features of the disease with minimal side effects are needed. As a new therapeutic approach, 1-(4-fluoro-phenyl)-4-((6bR
Kimberly E Vanover et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 44(3), 598-605 (2018-11-20)
Dopamine D2 receptor occupancy (D2RO) is a key feature of all currently approved antipsychotic medications. However, antipsychotic efficacy associated with high D2RO is often limited by side effects such as motor disturbances and hyperprolactinemia. Lumateperone (ITI-007) is a first-in-class selective
Peng Li et al.
Journal of medicinal chemistry, 57(6), 2670-2682 (2014-02-25)
We report the synthesis and structure-activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT(2A) 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

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