Lumateperone PTSA salt | ITI-722 | ITI007 | CAS#1187020-80-9 | 313368-91-1 | 5HT2A antagonist

MedKoo Cat#: 319582 | Name: Lumateperone tosylate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lumateperone toluenesulfonic acid or Lumateperone PTSA salt, also known as ITI-722 or ITI-007, is a highly potent 5HT2A antagonist for the treatment of sleep maintenance insomnia. Preclinical data has shown that ITI-722 is not sedating and should not exhibit next day hangover effects that are commonly associated with other sleep medications. ITI-722 is expected to have a strong safety profile with no addiction liability.

Chemical Structure

Lumateperone tosylate

CAS#1187020-80-9 (tosylate)

Theoretical Analysis

MedKoo Cat#: 319582

Name: Lumateperone tosylate

CAS#: 1187020-80-9 (tosylate)

Chemical Formula: C31H36FN3O4S

Exact Mass: 393.2216

Molecular Weight: 565.70

Elemental Analysis: C, 65.82; H, 6.41; F, 3.36; N, 7.43; O, 11.31; S, 5.67

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 weeks
50mg	USD 450.00	2 weeks
100mg	USD 750.00	2 weeks
200mg	USD 1,050.00	2 weeks
500mg	USD 1,850.00	2 weeks
1g	USD 2,650.00	2 weeks
2g	USD 4,650.00	2 weeks

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Related CAS #

1187020-80-9 (tosylate) 313368-91-1 (free base)

Synonym

ITI-722; ITI722; ITI 722; ITI-007; ITI007; ITI 007; Lumateperone, Caplyta,

IUPAC/Chemical Name

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 toluenesulfonic acid

InChi Key

LHAPOGAFBLSJJQ-GUTACTQSSA-N

InChi Code

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

SMILES Code

O=C(C1=CC=C(F)C=C1)CCCN2CC[C@@](N3CCN(C)C4=C3C5=CC=C4)([H])[C@@]5([H])C2.CC6=CC=C(S(=O)(O)=O)C=C6

Appearance

Solid powder

Purity

>98% (chemical purity); > 98%(optical purity).

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, not in water

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lumateperone (ITI-007) tosylate is a 5-HT2A receptor antagonist (Ki = 0.54 nM).

In vitro activity:

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-HT(2A) antagonist, postsynaptic D2 antagonist, and inhibitor of serotonin transporter. Reference: J Med Chem. 2014 Mar 27;57(6):2670-82. https://pubmed.ncbi.nlm.nih.gov/24559051/

In vivo activity:

The results demonstrate that lumateperone; i) significantly suppressed CAR in rats, indicating an antipsychotic-like effect, ii) facilitated NMDA and AMPA receptor-mediated currents in the mPFC, in a dopamine D1-dependent manner, and iii) significantly increased dopamine and glutamate release in the rat mPFC. Reference: Eur Neuropsychopharmacol. 2022 Sep;62:22-35. https://pubmed.ncbi.nlm.nih.gov/35878581/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	44.19
	DMF:PBS (pH 7.2) (1:7)	0.1	0.21
	DMSO	55.0	97.22
	Ethanol	1.0	1.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 565.70 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. Li P, Zhang Q, Robichaud AJ, Lee T, Tomesch J, Yao W, Beard JD, Snyder GL, Zhu H, Peng Y, Hendrick JP, Vanover KE, Davis RE, Mates S, Wennogle LP. Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders. J Med Chem. 2014 Mar 27;57(6):2670-82. doi: 10.1021/jm401958n. Epub 2014 Mar 5. PMID: 24559051. 2. Dutheil S, Watson LS, Davis RE, Snyder GL. Lumateperone Normalizes Pathological Levels of Acute Inflammation through Important Pathways Known to Be Involved in Mood Regulation. J Neurosci. 2023 Feb 1;43(5):863-877. doi: 10.1523/JNEUROSCI.0984-22.2022. Epub 2022 Dec 22. PMID: 36549907. 3. Titulaer J, Radhe O, Danielsson K, Dutheil S, Marcus MM, Jardemark K, Svensson TH, Snyder GL, Ericson M, Davis RE, Konradsson-Geuken Å. Lumateperone-mediated effects on prefrontal glutamatergic receptor-mediated neurotransmission: A dopamine D1 receptor dependent mechanism. Eur Neuropsychopharmacol. 2022 Sep;62:22-35. doi: 10.1016/j.euroneuro.2022.06.009. Epub 2022 Jul 22. PMID: 35878581.

In vitro protocol:

In vivo protocol:

1. Dutheil S, Watson LS, Davis RE, Snyder GL. Lumateperone Normalizes Pathological Levels of Acute Inflammation through Important Pathways Known to Be Involved in Mood Regulation. J Neurosci. 2023 Feb 1;43(5):863-877. doi: 10.1523/JNEUROSCI.0984-22.2022. Epub 2022 Dec 22. PMID: 36549907. 2. Titulaer J, Radhe O, Danielsson K, Dutheil S, Marcus MM, Jardemark K, Svensson TH, Snyder GL, Ericson M, Davis RE, Konradsson-Geuken Å. Lumateperone-mediated effects on prefrontal glutamatergic receptor-mediated neurotransmission: A dopamine D1 receptor dependent mechanism. Eur Neuropsychopharmacol. 2022 Sep;62:22-35. doi: 10.1016/j.euroneuro.2022.06.009. Epub 2022 Jul 22. PMID: 35878581.

1: Vyas P, Hwang BJ, Brašić JR. An evaluation of lumateperone tosylate for the treatment of schizophrenia. Expert Opin Pharmacother. 2019 Nov 30:1-7. doi: 10.1080/14656566.2019.1695778. [Epub ahead of print] PubMed PMID: 31790322. 2: Krogmann A, Peters L, von Hardenberg L, Bödeker K, Nöhles VB, Correll CU. Keeping up with the therapeutic advances in schizophrenia: a review of novel and emerging pharmacological entities. CNS Spectr. 2019 Aug;24(S1):38-69. doi: 10.1017/S109285291900124X. PubMed PMID: 31482779. 3: Davis JM. Commentary on: Corponi F., Fabbri C, Bitter, I. Montgomery, S., Vieta, E., Kaspar, S., Pallanti S., Serretti A. Novel antipsychotics specificity profile: A clinically oriented review of lurasidone, brexpiprazole, cariprazine and lumateperone. Eur Neuropsychopharmacol. 2019 Sep;29(9):1061-1062. doi: 10.1016/j.euroneuro.2019.07.001. Epub 2019 Jul 29. PubMed PMID: 31371104. 4: Corponi F, Fabbri C, Bitter I, Montgomery S, Vieta E, Kasper S, Pallanti S, Serretti A. Novel antipsychotics specificity profile: A clinically oriented review of lurasidone, brexpiprazole, cariprazine and lumateperone. Eur Neuropsychopharmacol. 2019 Sep;29(9):971-985. doi: 10.1016/j.euroneuro.2019.06.008. Epub 2019 Jun 27. Review. PubMed PMID: 31255396. 5: Ahmed M, Malik M, Teselink J, Lanctôt KL, Herrmann N. Current Agents in Development for Treating Behavioral and Psychological Symptoms Associated with Dementia. Drugs Aging. 2019 Jul;36(7):589-605. doi: 10.1007/s40266-019-00668-7. Review. PubMed PMID: 30957198. 6: Kumar B, Kuhad A, Kuhad A. Lumateperone: a new treatment approach for neuropsychiatric disorders. Drugs Today (Barc). 2018 Dec;54(12):713-719. doi: 10.1358/dot.2018.54.12.2899443. Review. PubMed PMID: 30596390. 7: Vanover KE, Davis RE, Zhou Y, Ye W, Brašić JR, Gapasin L, Saillard J, Weingart M, Litman RE, Mates S, Wong DF. Dopamine D(2) receptor occupancy of lumateperone (ITI-007): a Positron Emission Tomography Study in patients with schizophrenia. Neuropsychopharmacology. 2019 Feb;44(3):598-605. doi: 10.1038/s41386-018-0251-1. Epub 2018 Oct 26. PubMed PMID: 30449883; PubMed Central PMCID: PMC6333832. 8: Jankowska A, Wesolowska A, Pawlowski M, Chlon-Rzepa G. Multi-Target-Directed Ligands Affecting Serotonergic Neurotransmission for Alzheimer's Disease Therapy: Advances in Chemical and Biological Research. Curr Med Chem. 2018;25(17):2045-2067. doi: 10.2174/0929867324666170529122802. Review. PubMed PMID: 28554324. 9: Citrome L. Emerging pharmacological therapies in schizophrenia: what's new, what's different, what's next? CNS Spectr. 2016 Dec;21(S1):1-12. doi: 10.1017/S1092852916000729. Review. PubMed PMID: 28044942.