NSI-189 | CAS#1270138-40-3 | MedKoo Biosciences

MedKoo Cat#: 510270 | Name: NSI-189

Description:

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

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

NSI-189

CAS#1270138-40-3 (free base)

Theoretical Analysis

MedKoo Cat#: 510270

Name: NSI-189

CAS#: 1270138-40-3 (free base)

Chemical Formula: C22H30N4O

Exact Mass: 366.2420

Molecular Weight: 366.50

Elemental Analysis: C, 72.10; H, 8.25; N, 15.29; O, 4.37

Price and Availability

Size	Price	Availability
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

1270138-40-3 (free base) 1270138-41-4 (phosphate)

Synonym

NSI-189; NSI 189; NSI189.

IUPAC/Chemical Name

(4-benzylpiperazin-1-yl)(2-(isopentylamino)pyridin-3-yl)methanone

InChi Key

DYTOQURYRYYNOR-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H30N4O/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/h3-9,11,18H,10,12-17H2,1-2H3,(H,23,24)

SMILES Code

O=C(N1CCN(CC2=CC=CC=C2)CC1)C3=CC=CN=C3NCCC(C)C

Appearance

white to off-white 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, 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:

NSI-189 is a nootropic and neurogenic research chemica.

In vitro activity:

TBD

In vivo activity:

ZDF (Zucker diabetic fatty) rats were maintained for 16 weeks of untreated diabetes before the start of oral treatment with NSI-189 for an additional 16 weeks. Treatment with NSI-189 selectively elevated the expression of protein subunits of complexes III and V and activities of respiratory complexes I and IV in the brain cortex, and this was accompanied by amelioration of impaired memory function and plasticity. In the sensory ganglia of ZDF rats, loss of AMPK activity was ameliorated by NSI-189, and this was accompanied by reversal of multiple indices of peripheral neuropathy. Reference: J Diabetes Res. 2022 Jul 4;2022:8566970. https://pubmed.ncbi.nlm.nih.gov/35967127/

	Solvent	mg/mL	mM
Solubility
	DMSO	73.0	199.18
	Ethanol	73.0	199.18

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 366.50 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.

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. 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. 2. 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.

In vitro protocol:

TBD

In vivo protocol:

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.