58993-78-5

Basic information

• Product Name: (S)-2-(4-Methoxyphenyl)-1-MethylethanaMine
• Synonyms: (S)-2-(4-Methoxyphenyl)-1-MethylethanaMine;(S)-2-(4-Methoxy-phenyl)-1-methyl-ethylamine;(1S)-2-(4-METHOXYPHENYL)-1-METHYLETHYLAMINE
• CAS NO: 58993-78-5
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Mol File: 58993-78-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 258.2±15.0 °C(Predicted)
• Appearance: /
• Density: 0.990±0.06 g/cm3(Predicted)
• PKA: 10.00±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(4-Methoxyphenyl)-1-MethylethanaMine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4-Methoxyphenyl)-1-MethylethanaMine(58993-78-5)
• EPA Substance Registry System: (S)-2-(4-Methoxyphenyl)-1-MethylethanaMine(58993-78-5)

Safety Data

• Hazardous Substances Data: 58993-78-5(Hazardous Substances Data)

Usage

General Description

(S)-2-(4-Methoxyphenyl)-1-MethylethanaMine, also known as 4-Methoxyamphetamine or PMA, is a psychoactive compound and member of the phenethylamine and amphetamine classes. It is a synthetic recreational drug that acts as a serotonin and norepinephrine reuptake inhibitor and a releasing agent. PMA is similar in structure and effects to MDMA (Ecstasy) but is known to be more potent and potentially more dangerous, with a higher risk of toxicity and overdose. It can cause symptoms such as hallucinations, hyperthermia, rapid heart rate, and hypertension, and has been associated with fatal overdoses and adverse health effects. The use of PMA is illegal in many countries and is considered a dangerous substance with a high potential for harm.

Upstream product

• 50505-66-3 [(S)-2-(4-Methoxy-phenyl)-1-methyl-ethyl]-((S)-1-phenyl-ethyl)-amine; hydrochloride 
• 37629-51-9 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 141-78-6 ethyl acetate 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 123-11-5 4-methoxy-benzaldehyde 
• 1352411-20-1 N-[2-(4'-methoxyphenyl)-1-methylethyl]-2-methoxyacetamide 
• 3938-96-3 ethyl 2-methoxyacetate 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 83-33-0 inden-1-one 
• 140-67-0 Estragole 

Downstream Products

• 67346-58-1 (S)-N-(1-(4-methoxyphenyl)propan-2-yl)acetamide 

Relevant articles and documents

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).

Reductive amination of ketones with ammonium catalyzed by a newly identified Brevibacterium epidermidis strain for the synthesis of (S)-chiral amines

The asymmetric reductive amination of achiral ketones with ammonia is a particularly attractive reaction for the synthesis of chiral amines. Although several engineered amine dehydrogenases have been developed by protein engineering for the asymmetric reductive amination of ketones, they all display (R)-stereoselectivity. To date, there is no report of an (S)-stereoselective biocatalyst for this reaction. Herein, a microorganism named Brevibacterium epidermidis ECU1015 that catalyzes the (S)-selective reductive amination of ketones with ammonium has been successfully isolated from soil. Using B. epidermidis ECU1015 as the catalyst, the asymmetric reductive amination of a set of phenylacetone derivatives was successfully carried out, yielding the corresponding (S)-chiral amines with moderate conversion and >99% enantiomeric excess.

A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds.