64220-40-2

Basic information

• Product Name: 5-chloro-2-methyl-1-indanone
• Synonyms: 5-chloro-2-methyl-1-indanone;5-Chloro-2-Methyl-2,3-dihydro-1H-inden-1-one;1H-Inden-1-one, 5-chloro-2,3-dihydro-2-methyl
• CAS NO: 64220-40-2
• Molecular Formula: C10H9ClO
• Molecular Weight: 181
• EINECS: 1533716-785-6
• Mol File: 64220-40-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-chloro-2-methyl-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-2-methyl-1-indanone(64220-40-2)
• EPA Substance Registry System: 5-chloro-2-methyl-1-indanone(64220-40-2)

Safety Data

• Hazardous Substances Data: 64220-40-2(Hazardous Substances Data)

Usage

General Description

5-chloro-2-methyl-1-indanone is a niche specialty chemical with a complex molecular structure. This organic compound is predominately used in research, scientific experiments, and in the development of pharmaceuticals. It features a chloro group, a methyl group, and a carbonyl group attached to a complex indanone ring. The chemical’s reactivity and properties are determined by these varied functional groups. However, exact details regarding its properties, uses, and safety precautions should be thoroughly checked from the databases of registered chemicals. As with all chemicals, appropriate safety measures should be employed when handling 5-chloro-2-methyl-1-indanone, due to its potentially harmful interactions.

Upstream product

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• 1186047-99-3 ethyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 42348-86-7 5-chloro-1-indanone 

Relevant articles and documents

Design and discovery of a high affinity, selective and β-arrestin biased 5-HT7 receptor agonist

Compound 1c, 5-chloro-2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-2,3-dihydro-1H-inden-1-one was previously reported from our laboratory showing high affinity binding to the 5-HT7 receptor (Ki = 0.5 nM). However, compound 1c racemizes readily upon enantiomeric separation. To prevent racemization, we have redesigned and synthesized methyl and carboxyethyl analogs, compounds 2 and 3 respectively, whose binding affinities were similar to those of compound 1c. Compounds 2 and 3 cannot undergo racemization since tautomerism was no longer possible and thus, compound 2 was selected for enantiomeric separation and further evaluation. Upon enantiomeric separation, the levorotatory enantiomer, (?)2 or 2a demonstrated a higher affinity (Ki = 1.2 nM) than the (+)2 or 2b enantiomer (Ki = 93 nM) and a β-arrestin biased functional selectivity for the 5-HT7 receptor. Although 2a showed about 8 times less activity than 5-HT in the Gs pathway, it showed over 31 times higher activity than 5-HT in the β-arrestin pathway. This constitutes a significant β-arrestin pathway preference and shows 2a to be more potent and more efficacious than the recently published β-arrestin biased 3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine, the N-debenzylated analog of JNJ18038683 (Compound 7). [Figure not available: see fulltext.]

ALKYLATED TETRAHYDROISOQUINOLINES FOR BINDING TO CENTRAL NERVOUS SYSTEM RECEPTORS

Derivatives of 1,2,3,4-tetrahydroisoquinoline (THIQ) having the general formula A-(CH2)n—B are provided, wherein A is THIQ or a substituted derivative thereof and B is an aryl, cycloalkylaryl, or cycloalkyl group, wherein A and B are linked to each other by an alkyl or substituted alkyl chain. The compounds are useful as selective ligands (agonists or antagonists) of central nervous system receptors, and in particular of the seratonin receptors. The compounds or their salts can be formulated into pharmaceutical in need thereof by any route of administration suitable for a desired treatment protocol and especially for the treatment of psychiatric disorders.