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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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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