NSI-189 Phosphate

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MedKoo CAT#: 565439

CAS#: 1270138-41-4 (phosphate)

Description: NSI-189 is a novel neurogenic molecule with pleiotropic properties, including antidepressant, procognitive, synaptoplastic, and neurotrophic activities demonstrated in preclinical studies. Its antidepressant activity is monoamine-independent. Histopathological assessment of stroke brains from NSI-189-treated animals revealed significant increments in neurite outgrowth as evidenced by MAP2 immunoreactivity that was prominently detected in the hippocampus and partially in the cortex. These results suggest NSI-189 actively stimulated remodeling of the stroke brain.

Chemical Structure

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NSI-189 Phosphate
CAS# 1270138-41-4 (phosphate)
Instruction

Theoretical Analysis

MedKoo Cat#: 565439
Name: NSI-189 Phosphate
CAS#: 1270138-41-4 (phosphate)
Chemical Formula: C22H33N4O5P
Exact Mass: 0.00
Molecular Weight: 464.500
Elemental Analysis: C, 56.89; H, 7.16; N, 12.06; O, 17.22; P, 6.67

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 1270138-40-3 (free base)   1270138-41-4 (phosphate)    

Synonym: NSI189 Phosphate; NSI 189 Phosphate; NSI-189 Phosphate;

IUPAC/Chemical Name: (2-((3-Methylbutyl)amino)-3-pyridinyl)(4-(phenylmethyl)-1-piperazinyl)-methanone phosphate

InChi Key: LWHMGALTTIYPJU-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H30N4O.H3O4P/c1-18(2)10-12-24-21-20(9-6-11-23-21)22(27)26-15-13-25(14-16-26)17-19-7-4-3-5-8-19;1-5(2,3)4/h3-9,11,18H,10,12-17H2,1-2H3,(H,23,24);(H3,1,2,3,4)

SMILES Code: O=C(C1=CC=CN=C1NCCC(C)C)N2CCN(CC3=CC=CC=C3)CC2.O=P(O)(O)O

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >3 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 464.50 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Zhu S, Shi J, Jin Q, Zhang Y, Zhang R, Chen X, Wang C, Shi T, Li L. Mitochondrial dysfunction following repeated administration of alprazolam causes attenuation of hippocampus-dependent memory consolidation in mice. Aging (Albany NY). 2023 Oct 5;15(19):10428-10452. doi: 10.18632/aging.205087. Epub 2023 Oct 5. PMID: 37801512; PMCID: PMC10599724.


2: Jolivalt CG, Aghanoori MR, Navarro-Diaz MC, Han MM, Sanchez G, Guernsey L, Quach D, Johe K, Fernyhough P, Calcutt NA. Enhancement of Mitochondrial Function by the Neurogenic Molecule NSI-189 Accompanies Reversal of Peripheral Neuropathy and Memory Impairment in a Rat Model of Type 2 Diabetes. J Diabetes Res. 2022 Jul 4;2022:8566970. doi: 10.1155/2022/8566970. PMID: 35967127; PMCID: PMC9372526.


3: Johe KK, Kay G, Kumar S, Burdick KE, McIntyre RS, Papakostas GI, Fava M. NSI-189 phosphate, a novel neurogenic compound, selectively benefits moderately depressed patients: A post-hoc analysis of a phase 2 study of major depressive disorder. Ann Clin Psychiatry. 2020 Aug;32(3):182-196. PMID: 32722729.


4: Jolivalt CG, Marquez A, Quach D, Navarro Diaz MC, Anaya C, Kifle B, Muttalib N, Sanchez G, Guernsey L, Hefferan M, Smith DR, Fernyhough P, Johe K, Calcutt NA. Amelioration of Both Central and Peripheral Neuropathy in Mouse Models of Type 1 and Type 2 Diabetes by the Neurogenic Molecule NSI-189. Diabetes. 2019 Nov;68(11):2143-2154. doi: 10.2337/db19-0271. Epub 2019 Sep 6. PMID: 31492662; PMCID: PMC6804627.


5: Papakostas GI, Johe K, Hand H, Drouillard A, Russo P, Kay G, Kashambwa R, Hoeppner B, Flynn M, Yeung A, Martinson MA, Fava M. A phase 2, double-blind, placebo-controlled study of NSI-189 phosphate, a neurogenic compound, among outpatients with major depressive disorder. Mol Psychiatry. 2020 Jul;25(7):1569-1579. doi: 10.1038/s41380-018-0334-8. Epub 2019 Jan 9. PMID: 30626911; PMCID: PMC7303010.


6: Liu Y, Johe K, Sun J, Hao X, Wang Y, Bi X, Baudry M. Enhancement of synaptic plasticity and reversal of impairments in motor and cognitive functions in a mouse model of Angelman Syndrome by a small neurogenic molecule, NSI-189. Neuropharmacology. 2019 Jan;144:337-344. doi: 10.1016/j.neuropharm.2018.10.038. Epub 2018 Nov 5. PMID: 30408487.


7: Bauman MD, Schumann CM, Carlson EL, Taylor SL, Vázquez-Rosa E, Cintrón-Pérez CJ, Shin MK, Williams NS, Pieper AA. Neuroprotective efficacy of P7C3 compounds in primate hippocampus. Transl Psychiatry. 2018 Sep 26;8(1):202. doi: 10.1038/s41398-018-0244-1. PMID: 30258178; PMCID: PMC6158178.


8: Allen BD, Acharya MM, Lu C, Giedzinski E, Chmielewski NN, Quach D, Hefferan M, Johe KK, Limoli CL. Remediation of Radiation-Induced Cognitive Dysfunction through Oral Administration of the Neuroprotective Compound NSI-189. Radiat Res. 2018 Apr;189(4):345-353. doi: 10.1667/RR14879.1. Epub 2018 Jan 19. PMID: 29351056; PMCID: PMC5910029.


9: McIntyre RS, Johe K, Rong C, Lee Y. The neurogenic compound, NSI-189 phosphate: a novel multi-domain treatment capable of pro-cognitive and antidepressant effects. Expert Opin Investig Drugs. 2017 Jun;26(6):767-770. doi: 10.1080/13543784.2017.1324847. Epub 2017 May 8. PMID: 28460574.


10: Tajiri N, Quach DM, Kaneko Y, Wu S, Lee D, Lam T, Hayama KL, Hazel TG, Johe K, Wu MC, Borlongan CV. NSI-189, a small molecule with neurogenic properties, exerts behavioral, and neurostructural benefits in stroke rats. J Cell Physiol. 2017 Oct;232(10):2731-2740. doi: 10.1002/jcp.25847. Epub 2017 Apr 25. PMID: 28181668; PMCID: PMC5518191.


11: Fava M, Johe K, Ereshefsky L, Gertsik LG, English BA, Bilello JA, Thurmond LM, Johnstone J, Dickerson BC, Makris N, Hoeppner BB, Flynn M, Mischoulon D, Kinrys G, Freeman MP. A Phase 1B, randomized, double blind, placebo controlled, multiple-dose escalation study of NSI-189 phosphate, a neurogenic compound, in depressed patients. Mol Psychiatry. 2016 Oct;21(10):1483-4. doi: 10.1038/mp.2016.140. Epub 2016 Aug 16. Erratum for: Mol Psychiatry. 2016 Oct;21(10 ):1372-80. PMID: 27528461; PMCID: PMC5030463.


12: Fava M, Johe K, Ereshefsky L, Gertsik LG, English BA, Bilello JA, Thurmond LM, Johnstone J, Dickerson BC, Makris N, Hoeppner BB, Flynn M, Mischoulon D, Kinrys G, Freeman MP. A Phase 1B, randomized, double blind, placebo controlled, multiple-dose escalation study of NSI-189 phosphate, a neurogenic compound, in depressed patients. Mol Psychiatry. 2016 Oct;21(10):1372-80. doi: 10.1038/mp.2015.178. Epub 2015 Dec 8. Erratum in: Mol Psychiatry. 2016 Oct;21(10):1483-4. PMID: 26643541; PMCID: PMC5030464.