245759-64-2

Usage

Uses

Used in Research Applications:
4-Methoxy-alpha-methyl-N-(phenylmethyl)benzeneethanamine is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its ability to increase the release of neurotransmitters like dopamine and norepinephrine makes it a valuable tool for understanding the mechanisms of action of stimulant drugs.
Used in Forensic Analysis:
In the field of forensic science, 4-Me-MA is utilized for the detection and identification of controlled substances in biological samples, such as blood, urine, or hair. Its unique chemical structure allows for accurate analysis and differentiation from other similar compounds.
Used in Drug Policy and Regulation:
4-Methoxy-alpha-methyl-N-(phenylmethyl)benzeneethanamine is used as a reference substance in the development and implementation of drug policy and regulation. Understanding its properties, effects, and potential for abuse helps inform the creation of guidelines and restrictions to protect public health and safety.

InChI:InChI=1/C17H21NO/c1-14(18-13-16-6-4-3-5-7-16)12-15-8-10-17(19-2)11-9-15/h3-11,14,18H,12-13H2,1-2H3

Upstream product

• 100-46-9 benzylamine 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 17199-29-0 (S)-Mandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 43229-65-8 [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine 
• 1049695-95-5 benzyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine; hydrochloride 

Downstream Products

• 43229-80-7 N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-(4-methoxyphenyl)-1-methylethyl]-amino]ethyl]phenyl]formamide 
• 73573-87-2 (R,R)-formoterol 
• 1198769-18-4 (R)-4-benzyloxy-3-nitro-α-(N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amino)acetophenone 
• 289657-26-7 (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 188690-83-7 N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide 
• 245759-65-3 (R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 87833-61-2 (S,S)-formoterol fumarate 
• 67346-49-0 (S,S)-formoterol 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF ARFORMOTEROL OR SALT THEREOF

Provided is an improved process for the preparation of arformoterol L-(+)-tartrate, and more specifically provided is a novel process for the preparation of arformoterol L-(+)-tartrate via arformoterol D-(?)-tartrate.

PROCESS FOR THE SYNTHESIS OF ARFORMOTEROL

The present invention provides a process for preparing a compound of formula (Vl) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an α-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (Vl), wherein the reduction is carried out in the presence of either (1 ) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein: R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.

PREPARATION OF (R,R)-FENOTEROL AND (R,R)- OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE

This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

Large-scale synthesis of enantio- and diastereomerically pure (R,R)-formoterol

(R,R)-Formoterol (1) is a long-acting, very potent β2-agonist, which is used as a bronchodilator in the therapy of asthma and chronic bronchitis. Highly convergent synthesis of enantio- and diastereomerically pure (R,R)-formoterol fumarate is achieved by a chromatography-free process with an overall yield of 44%. Asymmetric catalytic reduction of bromoketone 4 using as catalyst oxazaborolidine derived from (1R, 2S)-1-amino-2-indanol and resolution of chiral amine 3 are the origins of chirality in this process. Further enrichment of enantio- and diastereomeric purity is accomplished by crystallizations of the isolated intermediates throughout the process to give (R,R)-formoterol (1) as the pure stereoisomer (ee, de >99.5%).