847574-01-0

Basic information

• Product Name: (4-methylpiperidin-1-yl)acetonitrile
• Synonyms: (4-methylpiperidin-1-yl)acetonitrile;4-Methyl-1-piperidineacetonitrile
• CAS NO: 847574-01-0
• Molecular Formula: C₈H₁₄N₂
• Molecular Weight: 138.21016
• Mol File: 847574-01-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-methylpiperidin-1-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (4-methylpiperidin-1-yl)acetonitrile(847574-01-0)
• EPA Substance Registry System: (4-methylpiperidin-1-yl)acetonitrile(847574-01-0)

Safety Data

• Hazardous Substances Data: 847574-01-0(Hazardous Substances Data)

Usage

General Description

(4-methylpiperidin-1-yl)acetonitrile is a chemical compound with the molecular formula C8H15N. It is a derivative of piperidine and belongs to the class of acetonitrile compounds. This chemical is used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is also used as an intermediate in the production of various organic compounds. (4-methylpiperidin-1-yl)acetonitrile has potential applications in the pharmaceutical industry due to its versatile reactivity and structural properties. However, it is important to handle this chemical with care and follow proper safety protocols when working with it.

Upstream product

• 626-58-4 4-methylpiperidin 

Downstream Products

• 847573-84-6 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(4-methylpiperidin-1-yl)ethyl]-2-iodo-4,5-dimethoxybenzamide 
• 14156-95-7 2-(4-methylpiperidin-1-yl)ethan-1-amine 

Relevant articles and documents

5-(2-Aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: Variation of N-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance

5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c, h]-[1,6]naphthyridin-6-one (ARC-111) has potent TOP1-targeting activity and pronounced antitumor activity. Several analogues of ARC-111 were synthesized with NH2, N-alkyl, N,N-dialkyl, pyrrolidinyl, piperidinyl, and piperazinyl substituents at the 2-position of the 5-ethyl group. The relative TOP1-targeting activity and cytotoxicity of these structural analogues were assessed in RPMI8402 and P388 tumor cells and their camptothecin-resistant variants CPT-K5 and P388/CPT45, respectively. Potent TOP1-targeting activity was retained within a series of mono N-alkyl analogues that included NHCH 2CH3, NHCH(CH3)2, and NHC(CH 3)3. TOP1-targeting activity was diminished by the presence of a N-benzyl moiety. In a comparison of a series of N-alkyl-N-isopropyl analogues, activity decreased in the order CH3 > CH2CH3 > CH-(CH3)2. Cytotoxicity in RPMI8402 and P388 did correlate with TOP1-targeting activity. Cytotoxic activity was also determined in KB3-1 cells and its variants KB/V-1 and KBH5.0. As KB/V-1 cells overexpress MDR1 and KBH5.0 cells overexpress BCRP, decreased cytotoxicity in these cell lines relative to the parent cell line is indicative of compounds that are substrates for these efflux transporters. In view of their diminished cytotoxicity in KB/V-1 cells, it appears that the likely demethylated metabolites of ARC-111, i.e., where NH2 or NHCH3 replaces the N(CH3)2 at the 2-position of the 5-ethyl substituent, are substrates for MDR1. In contrast, no significant difference in cytotoxicity among these three cell lines was observed with other N-alkyl analogues, including NHC2H5, NHCH(CH 3)2, NHC(CH3)3, N(CH 3)2, N(CH2CH3)2, NCH 3(CH-(CH3)2), and either the pyrrolidinyl or the piperidinyl analogues. The 2-(piperazinyl) analogues were associated with diminished cytotoxicity in KB/V-1 cells, suggesting that the second basic amino substituent is associated with their recognition as substrates by MDR1. Comparative studies on the antitumor activity of ARC-111 and its N-demethylated derivatives (the NHCH3 and NH2 analogues) against SJ-BT45 medulloblastoma xenografts in seid mice revealed that the secondary amine metabolite is at least as active as ARC-111 in vivo, although the primary amine derivative was significantly less potent.