70428-92-1

Usage

Chemical class

Phenylalkylamine

Derivative of

Phenmetrazine

Use

Previously used for the treatment of obesity (phenmetrazine)

Modification

Addition of a trifluoromethyl group to the phenyl ring

Purpose of modification

To enhance potency and pharmacological effects

Identification

As a novel psychoactive substance and designer drug

Effects

Stimulant properties similar to other phenmetrazine derivatives

Risks

Potential for addiction, overdose, and adverse health effects

Legal status

Subject to legal restrictions in many jurisdictions, not recommended for any purposes.

Upstream product

• 1069136-42-0 N-(3-trifluoromethylphenylmethyl)xanthone imine 
• 108-90-7 chlorobenzene 
• 57891-96-0 C₁₄H₁₀F₃N 

Downstream Products

• 1069136-45-3 N-(phenyl(3-(trifluoromethyl)phenyl)methyl)benzamide 

Relevant academic research and scientific papers

Aminoimidazoles as potent and selective human β-secretase (BACE1) inhibitors

The identification of small molecule aminoimidazoles as potent and selective human β-secretase inhibitors is reported. These analogues demonstrate low nannomolar potency for BACE1 in a FRET assay, exhibit comparable activity in a cell-based (ELISA) assay, and show>100x selectivity for the other structurally related aspartyl proteases BACE2, cathepsin D, renin, and pepsin. Our design strategy was supported by molecular modeling studies based on the cocrystal structure of the HTS-hit 3 in the BACE1 active site. These strategies enabled us to integrate pyridine and pyrimidine groups on 3 extending deep into the S3 region of the BACE1 binding pocket and enhancing the ligand's potency. Compound (R)-37 displayed an IC50 value for BACE1 of 20 nM, cellular activity of 90 nM, and > 100-fold selectivity over related aspartyl proteases. Acute oral administration of (R)-37 at 30 mg/kg resulted in a significant 71% reduction of plasma Aβ40 measured at the 6 h time point in a Tg2576 mouse model (p 0.001). 2009 American Chemical Society.

Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described.

Palladium-catalyzed benzylic arylation of N-benzylxanthone imine

(Chemical Equation Presented) The direct benzylic arylation of N-benzylxanthone imine with aryl chloride proceeds under palladium catalysis, yielding the corresponding coupling product. The product is readily transformed to benzhydrylamine. Taking into consideration that the imine is readily available from benzylic amine, the overall transformation represents a formal cross-coupling reaction of aryl halide with α-aminobenzyl metal.

Substituted benzhydryl lactamimide derivatives

Novel compounds useful as diuretic agents and anticoagulants are represented by the following formula SPC1 Wherein m is a positive whole integer of from 1 to 3; n is a positive whole integer of from 3 to 7; R and R1 may be the same or different