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N161

Sigma-Aldrich

NPC-15437 dihydrochloride hydrate

≥97% (NMR), powder

Synonym(s):

(S)-2,6-Diamino-N-[(1-(1-oxotridecyl)-2-piperidinyl)methyl]hexanamide dihydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C25H50N4O2 · 2HCl · xH2O
CAS Number:
141774-20-1
Molecular Weight:
511.61 (anhydrous basis)
MDL number:
MFCD00210207
UNSPSC Code:
12352200
PubChem Substance ID:
24897504
NACRES:
NA.77

assay

≥97% (NMR)

form

powder

storage condition

desiccated

color

white

solubility

H2O: 10 mg/mL, clear

Storage temp.

2-8°C

SMILES string

Cl[H].Cl[H].CCCCCCCCCCCCC(=O)N1CCCCC1CNC(=O)[C@@H](N)CCCCN

InChI

1S/C25H50N4O2.2ClH/c1-2-3-4-5-6-7-8-9-10-11-18-24(30)29-20-15-13-16-22(29)21-28-25(31)23(27)17-12-14-19-26;;/h22-23H,2-21,26-27H2,1H3,(H,28,31);2*1H/t22?,23-;;/m0../s1

Inchi Key

RISSBZWRJRRXTD-OLBPYZPGSA-N

Application

NPC-15437 dihydrochloride hydrate has been used as a protein kinase C (PKC) inhibitor:
  • to test its blocking effect on nicotine-seeking behavior in mice in drug-paired cues
  • along with cocaine to test its effect on 3,4-methylenedioxymethamphetamine (MDMA)-induced neurotoxicity in mice
  • to study its effect on PKC signaling in object recognition memory studies

Biochem/physiol Actions

NPC 15437 is also reported to be a P-glycoprotein (Pgp) modulator.
Selective protein kinase C inhibitor.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ainhoa Plaza-Zabala et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 38(9), 1724-1736 (2013-03-23)
Hypocretin/orexin signaling is critically involved in relapse to drug-seeking behaviors. In this study, we investigated the involvement of the hypocretin system in the reinstatement of nicotine-seeking behavior induced by nicotine-associated cues. Pretreatment with the hypocretin receptor-1 antagonist SB334867, but not
J P Sullivan et al.
FEBS letters, 285(1), 120-123 (1991-07-08)
We recently demonstrated that 2,6,diamino-N-[( 1-(oxotridecyl)-2-piperidinyl]methyl)-hexanamide (NPC 15437) is a selective inhibitor of PKC interacting at the regulatory domain of the enzyme. To further investigate the interaction of NPC 15437 with PKC we expressed a series of cDNAs encoding mutant
I Peraile et al.
British journal of pharmacology, 159(1), 201-211 (2009-12-18)
3,4-Methylenedioxymethamphetamine (MDMA) and cocaine are two widely abused psychostimulant drugs targeting the dopamine transporter (DAT). DAT availability regulates dopamine neurotransmission and uptake of MDMA-derived neurotoxic metabolites. We aimed to determine the effect of cocaine pre-exposure on the acute and long-term
E C Sha et al.
Investigational new drugs, 13(4), 285-294 (1996-01-01)
We assessed the effect of the protein kinase C inhibitor 2,6-diamino-N-([1-(1-oxotridecyl)-2-piperidinyl]methyl)hexanami de (NPC 15437) on the action of anthracyclines, epipodophyllotoxins and vinca alkaloids in P-glycoprotein (Pgp)-expressing CH(R)C5 hamster ovary and MCF-7/Adria(R) human breast cancer cells. Flow microfluorimetry revealed that treatment
J P Sullivan et al.
Molecular pharmacology, 41(1), 38-44 (1992-01-01)
NPC 15437 is a prototype member of a new class of synthetically derived protein kinase C (PKC) inhibitors. PKC activity and binding of phorbol ester to the enzyme were inhibited by NPC 15437, with IC50 values of 19 +/- 2
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