20308-70-7

Usage

Class

Synthetic stimulant drug, cathinone class

Effects

Stimulant effects similar to amphetamines (increased energy, alertness, euphoria)

Use

Commonly used research chemical, found in illicit drug formulations (e.g. "bath salts" and "legal highs"), considered a designer drug

Legal status

Not well-regulated, created to mimic the effects of illegal drugs while circumventing drug laws

Adverse effects

Hallucinations, paranoia, cardiovascular problems

Long-term health effects

Not well-understood

InChI:InChI=1/C13H25NO/c1-2-3-4-5-6-7-10-13(15)14-11-8-9-12-14/h2-12H2,1H3

Upstream product

• 6212-93-7 N-Methylpelargonamide 
• 123-75-1 pyrrolidine 
• 60420-33-9 3-nonanoyloxazolidin-2-one 
• 764-85-2 Nonanoyl chloride 
• 63412-06-6 N-methyl-N-nitrosobenzamide 
• 109-89-7 diethylamine 
• 19211-35-9 N-Methyl-N-nitrosopelargonamide 
• 91083-84-0 N-Methyl-N-nitropelargonamide 

Downstream Products

• 111-87-5 octanol 
• 124-13-0 Octanal 
• 2216-87-7 undecan-3-one 
• 123-29-5 ethyl pelargonate 
• 125950-58-5 2-Fluoro-nonanoic acid ethyl ester 

Relevant academic research and scientific papers

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to α-keto amides and α-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.

Reaction of N-Nitroso- and N-Nitro-N-alkylamides with Amines

Several N-nitroso- and N-nitrocarboxamides have been characterized by 1H and 13C NMR spectroscopy.These compounds react with ammonia and aliphatic amines to afford mainly carboxamides of general formula RCONH2, RCONHR', or RCONR'R''.N-Nitrosocarboxamides and aromatic amines give poor yields of RCONHAr; by contrast, N-nitrocarboxamides and aromatic amines lead to RCONHAr in good yields.The higher thermal stability of the N-nitroamides as compared to N-nitrosoamides is advantageous in this connection; nevertheless, the principal advantage of the NNO2 group appears to be that it activates the nucleophilic attack to the carbonyl of the amide function more than the NNO group, as has been demonstrated by competitive experiments.The reaction of N-nitroso- and N-nitro-N-methylsulfonamides with ammonia and diethylamine has been studied as well; whereas N-methyl-N-nitro-p-toluenesulfonamide reacts as N-nitrocarboxamides, transnitration is predominant with N-methyl-N-nitroso-p-toluenesulfonamide.