24152-96-3

Basic information

• Product Name: 2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL
• Synonyms: 2-Amino-1-morpholinoethanone hydrochloride;4-Glycylmorpholine hydrochloride;2-Amino-1-(4-morpholinyl)ethanone hydrochloride 98%;2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL;2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HYDROCHLORIDE;2-AMINO-1-MORPHOLINO-1-ETHANONE HYDROCHLORIDE;2-Amino-1-morpholin-4-yl-1-ethanone hydrochloride;2-Amino-1-morpholin-4-yl-ethanonexHCl
• CAS NO: 24152-96-3
• Molecular Formula: C₆H₁₂N₂O₂*ClH
• Molecular Weight: 180.63
• Mol File: 24152-96-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 245-246°C
• Boiling Point: 332.6 °C at 760 mmHg
• Flash Point: 155 °C
• Appearance: /
• Vapor Pressure: 0.000104mmHg at 25°C
• Storage Temp.: 2-8°C
• BRN: 3702996
• CAS DataBase Reference: 2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL(24152-96-3)
• EPA Substance Registry System: 2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL(24152-96-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 24152-96-3(Hazardous Substances Data)

Usage

General Description

2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL, also known as morpholinylethylketone, is a chemical compound that contains a morpholine ring and an amino group attached to an ethanone molecule. It is commonly used as a pharmaceutical intermediate in the synthesis of various medications, such as antiviral and anticancer drugs. The HCL form of the compound refers to its salt form, which is often used for easier handling and storage. This chemical is important in the pharmaceutical industry for its potential therapeutic applications and as a building block for the synthesis of other compounds.

InChI:InChI=1/C6H12N2O2.ClH/c7-5-6(9)8-1-3-10-4-2-8;/h1-5,7H2;1H

Upstream product

• 114703-81-0 (2-morpholin-4-yl-2-oxo-ethyl)-carbamic acid tert-butyl ester 
• 864528-04-1 2-azido-1-(morpholin-4-yl)ethan-1-one 

Downstream Products

• 58792-05-5 4-[5-(4-chloro-phenoxymethyl)-[1,2,3]thiadiazole-4-carbonyl]-morpholine 
• 1355040-42-4 methyl 3-[(2,4-dichlorobenzoyl)-(2-morpholino-2-oxo-ethyl)amino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate 
• 1355040-41-3 methyl 3-[(4-chlorobenzoyl)-(2-morpholino-2-oxo-ethyl)amino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate 
• 1355040-43-5 methyl 5-(3,3-dimethylbut-1-ynyl)-3-[(4-methylbenzoyl)-(2-morpholino-2-oxo-ethyl)amino]thiophene-2-carboxylate 
• 1356556-35-8 ethyl 4-(4-(morpholine-4-carbonyl)-1H-imidazol-1yl)benzoate 
• 1356556-38-1 (1-(4-nitrophenyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-32-5 (1-(4-methoxyphenyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-65-4 (R)-(1-(1-phenylethyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-40-5 (1-(2,6-diisopropylphenyl)-1H-imidazol-4-yl)(morpholino)methanone 

Relevant articles and documents

Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification

Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50values ranging from 15 to 125?μM. These derivatives were selective inhibitors for the parasitic proteases, being unable to inhibit mammalian cathepsins B and S. The most active compound against cruzain (compound 5a; IC50?=?15?μM) is considerably more synthetically accessible than 1, while retaining its ligand efficiency. As observed for the original lead, compound 5a was shown to be a competitive enzyme inhibitor. In addition, it was also active against T. cruzi (IC50?=?67.7?μM). Interestingly, the pyrimidine derivative 4b, although inactive in enzymatic assays, was highly active against T. cruzi (IC50?=?3.1?μM) with remarkable selectivity index (SI?=?128) compared to uninfected fibroblasts. Both 5a and 4b exhibit drug-like physicochemical properties and are predicted to have a favorable ADME profile, therefore having great potential as candidates for lead optimization in the search for new drugs to treat Chagas disease.

Inhibitors of Cyclic AMP Phosphodiesterase. 4. Synthesis and Evaluation of Potential Prodrugs of Lixazinone (N-Cyclohexyl-N-methyl-4quinazolin-7-yl)oxy>butyramide, RS-82856)

The cyclic AMP phosphodiesterase (cAMP PDE) inhibitor and cardiotonic agent lixazinone (N-cyclohexyl-N-methyl-4-quinazolin-7-yl)oxy>butyramide, RS-82856, 1) and its acid and base addition salts were found to be insufficiently soluble in formulations suitable for intravenous administration.These results prompted an investigation into potential prodrugs with enhanced aqueous solubility designed to deliver 1 by three distinct mechanisms: (1) decarboxylation of α-carboxamides; (2) hydrolytic loss of a solubilizing N-1-(acyloxy)methyl or (N,N-dialkylamino)methyl moiety; or (3) intramolecular closure of a guanidino ester or amide.The target compounds were evaluated as delivery systems for 1 by three criteria: (1) chemical conversion rate to 1 under physiological conditions; (2) inhibition of type IV cAMP PDE at a fixed time point; and (3) in vivo inotropic activity in anesthetized dogs by both intravenous and oral administration.Release of 1 from 4a (series 1) was found to be too slow to be of value as prodrug of 1, since decarboxylation could be induced only by strong acid, conditions under which hydrolytic ring opening was found to severely compete.Conversely, 1 was released too readily on exposure of (N,N-dialkylamino)methyl derivatives such as 8d (series 2) to physiological conditions, although no large increase in aqueous solubility was realized.Finally, both the physicochemical and in vitro studies indicated that ring closure of the guanidinium esters and amides 17a-k (series 3) to 1 was quantitative and pH- and time-dependent, suggesting the possibility of delivery of the open, water-soluble prodrug form, followed by closure to 1 in plasma.Detailed examination of these agents in vivo, however, demonstrated that only those compounds that rapidly cyclized to 1, as measured by plasma levels of 1, exhibited inotropic activity, indicating that the open prodrug form was not efficiently absorbed upon oral administration.