492-39-7

Usage

Uses

Used in Pharmaceutical Industry:
Cathine Hydrochloride is used as an active pharmaceutical ingredient for its stimulant properties, which can help in the treatment of certain medical conditions. It is used for [application reason] due to its ability to stimulate the central nervous system and provide temporary relief from fatigue.
Used in Weight Loss Products:
Cathine Hydrochloride is used as an ingredient in weight loss products for its appetite-suppressing effects. It is used as a weight loss aid for [application reason] because it can help individuals control their food intake and potentially promote weight loss.
Used in Branded Medications:
Cathine Hydrochloride is used in various branded medications, such as Adiposetten n, Amorphan depot, Andiposetten, Appetrol, Dietene, Exponcit, Insacial, Miniscap, Minusin depot, Mirapront n, Neo-soldana, Novese, Phyteia schlankheitsdragees, Reduform, Redufrom, and Thinz. It is used as a key component in these medications for [application reason], which may include its stimulant and appetite-suppressing properties.

World Health Organization (WHO)

Cathine, a sympathomimetic amine, was formerly widely available in proprietary anorexic preparations. As dependence can occur and abuse has been reported, cathine has recently (1986) been subjected to control under Schedule III of the 1971 Convention on Psychotropic Substances. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)

Safety Profile

Poison by subcutaneous route.When heated to decomposition it emits toxic vapors ofNOx.

InChI:InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 54680-46-5 norephedrine 
• 611-71-2 (R)-Mandelic Acid 
• 917-64-6 methyl magnesium iodide 
• 131350-12-4 (S)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 67755-90-2 (S)-2-(1-ethoxyethoxy)-2-phenylacetonitrile 
• 132273-10-0 benzostabase of Ala-OMe 
• 123367-08-8 (S)-1-Phenyl-2-pyrrol-1-yl-propan-1-ol 
• 154-41-6 threo-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 20993-63-9 ((S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid ethyl ester 
• 7647-01-0 hydrogenchloride 
• 17097-67-5 (4S,5S)-4-methyl-5-phenyl-oxazolidin-2-one 
• 79-24-3 Nitroethane 
• 100-52-7 benzaldehyde 

Downstream Products

• 17097-67-5 (4S,5S)-4-methyl-5-phenyl-oxazolidin-2-one 
• 93730-38-2 (1S:2S)-2-benzylidenehydrazinocarbonylamino-1-phenyl-propanol-⁽¹⁾ 
• 91111-09-0 (1S:2S)-2-benzenesulfonylamino-1-phenyl-propanol-⁽¹⁾ 
• 64868-34-4 (+)N-methyl-ψ-ephedrine methiodide 
• 93428-31-0 (1S:2S)-2-hydrazinocarbonylamino-1-phenyl-propanol-⁽¹⁾ 
• 27780-30-9 trans-4S,5S-2-amino-4-methyl-5-phenyl-Δ²-oxazoline 
• 126188-49-6 (1S,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-acetamid 
• 353268-59-4 (1S,2S)-1-Phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propan-1-ol 
• 117409-04-8 (4S,5S)-(-)-4-Methyl-5-phenyl-2-(2-pyridinyl)-2-oxazolin 
• 145416-68-8 (1S,2S)-N,N-Dimethyl-N'-<(2-hydroxy-2-phenyl)-1-methylethyl>-harnstoff 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 57237-16-8 Norpseudoephedrin-hydroxylamin 
• 93-55-0 1-phenyl-propan-1-one 
• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 

Relevant academic research and scientific papers

High Regio- and Stereoselective Multi-enzymatic Synthesis of All Phenylpropanolamine Stereoisomers from β-Methylstyrene

We present a one-pot cascade for the synthesis of phenylpropanolamines (PPAs) in high optical purities (er and dr up to >99.5 %) and analytical yields (up to 95 %) by using 1-phenylpropane-1,2-diols as key intermediates. This bioamination entails the combination of an alcohol dehydrogenase (ADH), an ω-transaminase (ωTA) and an alanine dehydrogenase to create a redox-neutral network, which harnesses the exquisite and complementary regio- and stereo-selectivities of the selected ADHs and ωTAs. The requisite 1-phenylpropane-1,2-diol intermediates were obtained from trans- or cis-β-methylstyrene by combining a styrene monooxygenase with epoxide hydrolases. Furthermore, in selected cases, the envisioned cascade enabled to obtain the structural isomer (1S,2R)-1-amino-1-phenylpropan-2-ol in high optical purity (er and dr >99.5 %). This is the first report on an enzymatic method that enables to obtain all of the four possible PPA stereoisomers in great enantio- and diastereo-selectivity.

Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation

The chelation-controlled arylation reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin-Anh controlled additions with organomagnesium and organolithium reagents.

Efficient 2-step biocatalytic strategies for the synthesis of all nor(pseudo)ephedrine isomers

Chiral 1,2-amino alcohols are important building blocks for chemistry and pharmacy. Here, we developed two different biocatalytic 2-step cascades for the synthesis of all four nor(pseudo)ephedrine (N(P)E) stereoisomers. In the first one, the combination of an (R)-selective thiamine diphosphate (ThDP)-dependent carboligase with an (S)- or (R)-selective ω-transaminase resulted in the formation of (1R,2S)-NE or (1R,2R)-NPE in excellent optical purities (ee >99% and de >98%). For the synthesis of (1R,2R)-NPE, space-time yields up to ～26 g L-1 d-1 have been achieved. Since a highly (S)-selective carboligase is currently not available for this reaction, another strategy was followed to complement the nor(pseudo)ephedrine platform. Here, the combination of an (S)-selective transaminase with an (S)-selective alcohol dehydrogenase yielded (1S,2S)-NPE with an ee >98% and a de >99%. Although lyophilized whole cells are cheap to prepare and were shown to be appropriate for use as biocatalysts, higher optical purities were observed with purified enzymes. These synthetic enzyme cascade reactions render the N(P)E-products accessible from inexpensive, achiral starting materials in only two reaction steps and without the isolation of the reaction intermediates. This journal is the Partner Organisations 2014.

Two steps in one pot: Enzyme cascade for the synthesis of nor(pseudo)ephedrine from inexpensive starting materials

Two steps in one pot: An enzyme cascade consisting of a lyase and an (R)- or (S)-selective ω-transaminase (TA) provides (1R,2R)-norpseudoephedrine and (1R,2S)-norephedrine in only two steps. The intermediate is not isolated in this one-pot reaction and the products are obtained in high enantio- and diastereomeric purity. Moreover, the by-product from the second reaction can be recycled to serve as the substrate for the first reaction. Copyright

Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution

Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

Charge-transfer interactions: An efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric henry reactions

An anthracenyl-modified chiral bis(oxazoline) copper complex has been demonstrated to efficiently promote nitroaldol reactions between structurally varying aldehydes and nitromethane or nitroethane. The catalyst was recovered through formation of a charge transfer complex between the chiral ligand and trinitrofluorenone and its subsequent precipitation with pentane. The efficiency of this procedure was proved through several consecutive catalytic cycles that allowed the sturdy formation of the expected product with a high enantioselectivity. The catalyst′s stability was also put to the test in an original multi-substrate procedure. Following the same recovery concept, a new heterogeneous procedure was tested for which trinitrofluorenone was covalently linked to a silica support. Asymmetric heterogeneous catalysis was performed under these conditions as one of the few examples demonstrating the potential catalyst recycling in nitroaldol reactions through reversible, non-covalent interactions. Copyright

Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf

Ephedra sinica Stapf (Ephedraceae) is a widely used Chinese medicinal plant (Chinese name: Ma Huang). The main active constituents of E. sinica are the unique and taxonomically restricted adrenergic agonists phenylpropylamino alkaloids, also known as ephedrine alkaloids: (1R,2S)-norephedrine (1S,2S)-norpseudoephedrine, (1R,2S)-ephedrine, (1S,2S)-pseudoephedrine, (1R,2S)-N-methylephedrine and (1S,2S)-N-methylpseudoephedrine. GC-MS analysis of freshly picked young E. sinica stems enabled the detection of 1-phenylpropane-1,2-dione and (S)-cathinone, the first two putative committed biosynthetic precursors to the ephedrine alkaloids. These metabolites are only present in young E. sinica stems and not in mature stems or roots. The related Ephedra foemina and Ephedra foliata also lack ephedrine alkaloids and their metabolic precursors in their aerial parts. A marked diversity in the ephedrine alkaloids content and stereochemical composition in 16 different E. sinica accessions growing under the same environmental conditions was revealed, indicating genetic control of these traits. The accessions can be classified into two groups according to the stereochemistry of the products accumulated: a group that displayed only 1R stereoisomers, and a group that displayed both 1S and 1R stereoisomers. (S)-cathinone reductase activities were detected in E. sinica stems capable of reducing (S)-cathinone to (1R,2S)-norephedrine and (1S,2S)-norpseudoephedrine in the presence of NADH. The proportion of the diastereoisomers formed varied according to the accession tested. A (1R,2S)-norephedrine N-methyltransferase capable of converting (1R,2S)-norephedrine to (1R,2S)-ephedrine in the presence of S-adenosylmethionine (SAM) was also detected in E. sinica stems. Our studies further support the notion that 1-phenylpropane-1,2-dione and (S)-cathinone are biosynthetic precursors of the ephedrine alkaloids in E. sinica stems and that the activity of (S)-cathinone reductases directs and determines the stereochemical branching of the pathway. Further methylations are likely due to N-methyltransferase activities.

METHOD OF PREPARING PSEUDONOREPHEDRINE

A method of making high diastereoselective and enantiomerically pure pseudonorephedrine and the hitherto unknown compound (1R,2R) pseudonorephedrine.

A biocatalytic Henry reaction - The hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions

(Figure Presented) Novel enzyme activity: Biocatalytic Henry reactions with nitromethane and nitroethane yielded the corresponding nitroalcohols with good enantio- and diastereo-control in the presence of the hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis. Molecular modeling and deuterated starting materials were used in mechanistic investigations.

A scalable and expedient method of preparing diastereomerically and enantiomerically enriched pseudonorephedrine from norephedrine

Norephedrine has been efficiently converted into the corresponding diastereomer pseudonorephedrine using a three step, one-pot reaction. The three step process involves treatment of norephedrine with di-tert-butyl dicarbonate (Boc2O); cyclization by way of mesylate formation at the alcohol; and lithium hydroxide mediated hydrolysis of the oxazolidinone. The diastereomeric purity was determined by HPLC and the enantiomeric purity was determined by optical activity measurements and chiral stationary phase HPLC analysis of the pseudonorephedrine oxazolidinone derivatives.