579-58-8

Usage

InChI:InChI=1/C9H11NO2/c1-7(11)10(2)8-3-5-9(12)6-4-8/h3-6,12H,1-2H3

Upstream product

• 579-10-2 N-acetyl-N-methylaniline 
• 108-24-7 acetic anhydride 
• 55-55-0 4-(methylamino)phenol sulphate 
• 150-75-4 N-methyl-p-aminophenol 
• 74295-19-5 N-(4-acetato-phenyl)-N-methylacetamide 
• 51-72-9 4-(methylamino)phenol sulfate 
• 127-09-3 sodium acetate 

Downstream Products

• 109701-27-1 N,N'-dimethyl-4,4'-(3-oxa-pentanediyldioxy)-di-aniline 
• 103644-46-8 1,5-bis-[4-(acetyl-methyl-amino)-phenoxy]-pentane 
• 102810-16-2 N-{5-[4-(acetyl-methyl-amino)-phenoxy]-pentyl}-phthalimide 
• 74295-19-5 N-(4-acetato-phenyl)-N-methylacetamide 
• 858677-99-3 4-(2-diethylamino-ethoxy)-N-methyl-aniline 
• 86817-50-7 N-(4-Methoxymethoxy-phenyl)-N-methyl-acetamide 
• 174003-48-6 1,4-bis(N-methyl-4-acetamidophenoxy)butane 
• 692249-91-5 acetic acid-(4-hydroxy-N-methyl-3-nitro-anilide) 
• 861593-23-9 acetic acid-(4-hydroxy-N-methyl-3,5-dinitro-anilide) 
• 109557-20-2 N-acetyl-1,4-bis(4-methyaminophenoxy)butane 
• 174003-52-2 1,4-bisbutane 
• 174003-49-7 1,4-bis(4-methylaminophenoxy)butane 
• 50894-68-3 (+/-)-ribaline 
• 41234-31-5 (+/-)-ribaline picrate salt 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics

We report the optimisation of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced apomorphine-induced climbing, MK-801-induced hyperactivity and DOI-induced head twitching without observable catalepsy, even at the highest dose tested. In addition, it exhibited suppression in a CAR test. Furthermore, in a novel object recognition task, it displayed procognition properties. Therefore, compound 11 is a promising candidate multi-target antipsychotic.

Fungicidal 2-aryl-2-cyano-2-(aryloxyalkyl)ethyl-1,2-4-triazoles

2-aryl-2-cyano-2-(aryloxyalkyl)ethyl-1,2,4-triazoles of the formula STR1 wherein Ar1 and Ar2 are optionally substituted aryl groups which may or may not be different, R is hydrogen or alkyl, n is an integer of at least one, and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes thereof, compositions containing these compounds and their uses as fungicides, particularly against phytopathogenic fungi.

Heterocyclic compounds

The use of compounds of formula (IIA) where R3 is halogen, CF3 or methyl, R4′is methyl or ethyl; and, R5′is OR6 or -NHSO2R7 wherein R6 is hydrogen, optionally substituted C1

Comparative Toxicities and Analgesic Activities of Three Monomethylated Analogues of Acetaminophen

Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen.Only 4'-hydroxy-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice.Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite.In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methlacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic.The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.

Formation and Reactions of the Cyclic Tautomers of Tryptophans and Tryptamines. VII. Hydroxylation of Tryptophans and Tryptamines

The 5-hydroxytryptophan derivative 12 was prepared in 60percent yield from the tryptophan derivative 8 by selective oxidation of the cyclic tautomer 9 with Fremy's salt or Pb(OAc)4-CF3COOH to the p-quinoneimine 10, followed by reduction and ring-opening.By analogous oxidation, serotonin was prepared from tryptamine.On the other hand, the oxidation of the Na-acetyl-cyclic tautomers (16 and 22) with Pb(OAc)4-CF3COOH followed by methylation gave the 5- and 6-methoxy derivatives (17, 18, 23, and 24) in 20-40percent yields.These compounds were readily converted to the 5- and 6-methoxytryptophan derivatives (20, 21) by acid treatment.These methods are the first practical hydroxylation procedures to be reported for tryptophans.Keywords: 5-hydroxytryptophan; methoxytryptophan; cyclic tautomer; tryptophan; oxidation; hydroxylation; lead tetraacetate; Fremy's salt.

Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines

N-Acetyl-2,6-dimethyl-p-benzoquinone imine and N-acetyl-3,5-dimethyl-p-benzoquinone imine were prepared from 2,6-dimethylacetaminophen and 3,5-dimethylacetaminophen by oxidation with lead tetraacetate. Reaction of N-acetyl-2,6-dimethyl-p-benzoquinone imine with hydrochloric acid gave 3'-chloro-2',6'-dimethyl-4'-hydroxyacetanilide, whereas ethanethiol, aniline, and ethanol gave tetrahedral adducts resulting from addition to the imine carbon. Water gave 2,6-dimethyl-p-benzoquinone. With N-acetyl-3,5-dimethyl-p-benzoquinone imine, water and aniline gave substitution on the imine carbon, yielding 2,6-dimethyl-p-benzoquinone and 3,5-dimethyl-N-phenyl-p-benzoquinone imine, respectively. Ethanethiol gave 3',5'-dimethyl-2'-(ethylthio)-4'-hydroxyacetanilide. The toxicity of 2,6-dimethylacetaminophen and 3,5-dimethylacetaminophen was examined histologically in mice and rats. 3,5-Dimethylacetaminophen was slightly more nephrotoxic but showed a similar hepatotoxicity to acetaminophen. 2,6-Dimethylacetaminophen, like N-methylacetaminophen, showed very little tissue damage.