552-79-4

Usage

Uses

1. Used in Pharmaceutical Industry:
(-)-N-Methylephedrine is used as an adrenergic agonist for its ability to stimulate the adrenergic receptors, which can help in treating conditions like asthma and hypotension. It is also used as an analeptic to counteract central nervous system depression.
2. Used in Chemical Synthesis:
(-)-N-Methylephedrine is used in conjunction with LiAlH4 (lithium aluminum hydride) for chiral reductions, which are important in the synthesis of various pharmaceutical compounds and other chiral molecules.
3. Used in Research and Development:
(-)-N-Methylephedrine serves as a valuable compound for research purposes, particularly in the study of adrenergic agonists, analeptics, and chiral chemistry. Its unique properties and applications make it a useful tool for understanding the mechanisms of action and potential therapeutic applications in various medical conditions.

References

Smith., J. Chern. Soc., 2056 (1927) Smith., ibid, 51 (1928) Smith., ibid, 2755 (1929) Wolfes., Arch. Pharrn., 268,327 (1930) Preparation: Nagai., J. Pharrn. Soc., Japan, No. 120, 109 (1892) Nagai, Kanao., ibid, 48, 145 (1928)

InChI:InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/p+1/t9-,11+/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 299-42-3 ephedrine 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 
• 74-88-4 methyl iodide 
• 1201-56-5 (+/-)-N-methylephedrine 
• 492-41-1 (1R,2S)-norephedrine 
• 541-41-3 chloroformic acid ethyl ester 
• 102146-08-7 (S)-3,3-Dimethoxy-2-methyl-propionic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester 
• 1630-35-9 (1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylformamid 
• 53135-04-9 (1R,2S)-(2-Dimethylamino-1-phenyl)propyl propanoate 
• 98171-04-1 Dimethyl-[(1S,2R)-1-methyl-2-phenyl-2-((E)-1-trimethylsilanyloxy-propenyloxy)-ethyl]-amine 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 90-82-4 pseudoephedrine 

Downstream Products

• 102550-23-2 bis-((1Ξ,2S)-2-dimethylamino-1-phenyl-propyl)-ether 
• 130894-10-9 (+)-2-((1R,2S)-2-dimethylamino-1-phenylpropoxy)pyridine 
• 139528-57-7 (1R,2S)-2-(N,N-dimethylamino)-1-phenyl-1-(N-phthalimidooxy)propane 
• 77452-67-6 (-)-N-benzyl-N-methylephedrinium chloride 
• 74059-53-3 (1R,2S)-N-methylephedrine pentanoate 
• 114264-02-7 (1R,2S)-2-(dimethylamino)-1-phenylpropyl octanoate 
• 103836-60-8 (1R,2S)-N-methylephedrine 3-methylbutanoate 
• 139528-59-9 (1R,2S)-<α-<1-(dimethylamino)ethyl>benzyl>diphenyl phosphine 
• 60999-91-9 (-)-(1R,2S)-N-hexadecyl-N,N-dimethylephedrinium bromide 
• 126253-51-8 (Z)-2-Benzoylamino-3-phenyl-acrylic acid (1S,2S)-2-dimethylamino-1-phenyl-propyl ester 
• 158837-60-6 O-<(1R,2S)-N-Methylephedrine>-N,N'-diisopropylisourea 
• 76116-15-9 (+)-(1S,2R)-2-dimethylamino-1-phenyl-1-diphenyl-phosphinoxy-propane 
• 161904-84-3 (1R,2S)-1-phenyl-2-dimethylaminopropyl 2-benzamidocinnamate 
• 942-45-0 (1S,2S)-β-chloro-N,N',α-trimethylbenzeneethanammonium chloride 

Relevant academic research and scientific papers

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

Efficient ruthenium-catalyzed N-methylation of amines using methanol

An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.

A general catalytic methylation of amines using carbon dioxide

Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright

Ephedrine-based diselenide: A promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C-C coupling reactions

The ephedrine-based diselenide appears as a new promiscuous catalyst, able to generate optically active alcohols by addition of organozinc to aldehydes (up to 97% ee), and shows powerful GPx like activity, reducing H2O 2 to water in only 16.33 min (eleven times faster than PhSeSePh).

Ephedrine- and pseudoephedrine-derived thioureas in asymmetric michael additions of keto esters and diketones to nitroalkenes

Ephedrine-derived bifunctional thioureas have been synthesized and applied as organocatalysts in Michael additions of 1,3-dicarbonyl compounds to nitroalkenes. Georg Thieme Verlag Stuttgart.

Synthesis of functionalized chiral ammonium, imidazolium, and pyridinium-based ionic liquids derived from ()-ephedrine using solvent-free microwave activation. Applications for the asymmetric Michael addition

An efficient procedure for the synthesis of functionalized chiral ammonium, imidazolium, and pyridinium-based ionic liquids derived from (IR, 2S)-ephedrine using solvent-free microwave activation has been described. Good yields were obtained in very short reaction time. These chiral ionic liquids were used as chiral reaction media for the asymmetric Michael addition, giving good yields and moderate enantioselectivities.

Stable-isotope dimethylation labeling combined with LC-ESI MS for quantification of amine-containing metabolites in biological samples

One of the challenges associated with metabolome profiling in complex biological samples is to generate quantitative information on the metabolites of interest. In this work, a targeted metabolome analysis strategy is presented for the quantification of amine-containing metabolites. A dimethylation reaction is used to introduce a stable isotopic tag onto amine-containing metabolites followed by LC-ESI MS analysis. This labeling reaction employs a common reagent, formaldehyde, to label globally the amine groups through reductive animation. The performance of this strategy was investigated in the analysis of 20 amino acids and 15 amines by LC-ESI MS. It is shown that the labeling chemistry is simple, fast (13C-dimethylation does not show any isotope effect on either RPLC or HILIC LC, indicating that 13C-labeling is a preferred approach for relative quantification of amine-containing metabolites in different samples. The isotopically labeled 35 amine-containing analogues were found to be stable and proved to be effective in overcoming matrix effects in both relative and absolute quantification of these analytes present in a complicated sample, human urine. Finally, the characteristic mass difference provides additional structural information that reveals the existence of primary or secondary amine functional groups in amine-containing metabolites. As an example, for a human urine sample, a total of 438 pairs of different amine-containing metabolites were detected, at signal-to-noise ratios of greater than 10, by using the labeling strategy in conjunction with RP LC-ESI Fourier-transform ion cyclotron resonance MS.

1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89 percent. The stereoelectronic effects operating in the reactions are discussed.

Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).