537-46-2

Usage

InChI:InChI=1/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1

Upstream product

• 7632-10-2 methamphetamin 
• 50-00-0 formaldehyd 
• 51-64-9 dexamfetamine 
• 299-42-3 ephedrine 
• 90-82-4 pseudoephedrine 
• 5650-44-2 (-)-Methcathinone 
• 50-98-6 ephedrine hydrochloride 
• 74-88-4 methyl iodide 
• 403736-21-0 (1Ξ,2S)-2-methylamino-1-phenyl-propan-1-ol 
• 124919-00-2 (-)cis-(2S:3R)-N-Methyl-2-methyl-3-phenylaziridin 
• 13148-28-2 (+)-(2S,3S)-trans-1,2-dimethyl-3-phenylaziridine 
• 79821-84-4 (S)-N-(benzenesulfonyl)amphetamine 
• 15547-39-4 N-<(S)-1-methyl-2-phenylethyl>formamide 
• 345-78-8 Novafed 

Downstream Products

• 110376-61-9 2-[methyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-ethanethiol 
• 107412-03-3 N-methyl-N-((S)-1-methyl-2-phenyl-ethyl)-Ξ-lactamide 
• 100369-72-0 N-methyl-N-((S)-1-methyl-2-phenyl-ethyl)-glycolamide 
• 72606-67-8 N-methyl-N-((S)-1-methyl-2-phenyl-ethyl)-β-alanine ethyl ester 
• 92702-06-2 Laevulinoyl- 
• 114351-96-1 Methyl-((S)-1-methyl-2-phenyl-ethyl)-penta-2,3-dienyl-amine; compound with oxalic acid 
• 132017-84-6 methyl-((S)-1-methyl-2-phenyl-ethyl)-phenethyl-amine 
• 89362-18-5 Methyl-((S)-1-methyl-2-phenyl-ethyl)-penta-2,3-dienyl-amine 
• 13733-43-2 methyl-((S)-1-methyl-2-phenyl-ethyl)-(3.3-diphenyl-allyl)-amine 
• 10205-33-1 3-[methyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-1.1-diphenyl-propanol-⁽¹⁾ 
• 156-08-1 benzphetamine 
• 5411-22-3 benzfetamine hydrochloride 
• 51-57-0 S-methamphetamine hydrochloride 
• 1207188-81-5 C₁₉H₂₄N₂O 

Relevant academic research and scientific papers

Direct reductive amination of ketones: Structure and activity of S-selective imine reductases from streptomyces

The importance and structural diversity of chiral amines is well-demonstrated by the myriad nonenzymatic methods for their chemical production. In nature, the production of amines is performed by transamination rather than by reduction of an imine precursor derived from the corresponding ketone. Imine reductases, however, show great potential in the reduction of cyclic imines that are stable towards hydrolysis in aqueous reaction media. Here, we report the catalytic activity of two S-selective imine reductases towards 3,4-dihydroisoquinolines and 3,4-dihydro-β-carbolines and their activity in the direct reductive amination of ketone substrates. The crystal structures of the enzyme from Streptomyces sp. GF3546 in complex with the cofactor NADPH and from Streptomyces aurantiacus in native form have been solved and refined to a resolution of 1.9 A.

AMPHETAMINE CONTROLLED RELEASE, PRODRUG, AND ABUSE-DETERRENT DOSAGE FORMS

The invention also relates to pharmaceutical compositions comprising highly pure amphetamine and amphetamine-class compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds, and to methods of manufacturing, delivering, and using the amphetamine compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

AMPHETAMINE CONTROLLED RELEASE, PRODRUG, AND ABUSE DETERRENT DOSAGE FORMS

The invention also relates to pharmaceutical compositions comprising highly pure amphetamine and amphetamine-class compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds, and to methods of manufacturing, delivering, and using the amphetamine compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds.

Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs

We report the use of a chiral Cu(II) 3D metal-organic framework (MOF) based on the tripeptide Gly-l-His-Gly (GHG) for the enantioselective separation of metamphetamine and ephedrine. Monte Carlo simulations suggest that chiral recognition is linked to preferential binding of one of the enantiomers as a result of either stronger or additional H-bonds with the framework that lead to energetically more stable diastereomeric adducts. Solid-phase extraction of a racemic mixture by using Cu(GHG) as the extractive phase permits isolating >50% of the (+)-ephedrine enantiomer as target compound in only 4 min. To our knowledge, this represents the first example of a MOF capable of separating chiral polar drugs.

Prevention of Illicit Manufacutre of Methamphetamine from Pseudoephedrine Using Food Flavor Excipients

The invention relates generally to ephedrine or pseudoephedrine compositions containing biocompatible organoleptic (food flavoring) excipients that would prevent the illicit manufacture of methamphetamine from ephedrine or pseudoephedrine.

A concise enantioselective synthesis of (R)-selegiline, (S)-benzphetamine and formal synthesis of (R)-sitagliptin via electrophilic azidation of chiral imide enolates

A concise and high yielding enantioselective synthesis of (R)-selegiline, an anti-Parkinson's drug, (S)-benzphetamine, an anti-obesity agent, and (S)-sitagliptin, an anti-diabetic drug has been described starting from commercially available starting materials employing Evans' electrophilic azidation of chiral imide enolates as a key chiral inducing step, which proceeds in a highly diastereoselective manner (>99%).

PREVENTION OF ILLICIT METHAMPHETAMINE MANUFACTURE FROM PSEUDOEPHEDRINE USING FOOD FLAVOR EXCIPIENTS

The invention relates generally to ephedrine or pseudoephedrine compositions containing biocompatible organoleptic excipients that would prevent the illicit manufacture of methamphetamine from ephedrine or pseudoephedrine. The organoleptic agents, typically used as food flavorings, are pyrazine based excipients, that when co-formulated with ephedrine or pseudoephedrine, prevent the isolation and converasion of pure methamphetamine.

Synthesis of Chiral Amphetamine Derivatives by Stereospecific, Regioselective Cuprate Addition Reaction with Aziridine Phosphoramidate Compounds

The invention includes processes for the synthesis of amphetamine, dexamphetamine, methamphetamine, derivatives of these, including their salts, and novel precursors and intermediates obtained thereby, by synthesizing aziridine phosphoramidate compounds in specified solvents at specified temperatures, and then converting to a novel aryl or aryl-alkyl phosphoramidate precursors using an organometallic compound such as a copper salt, where the novel aryl or aryl-alkyl phosphoramidate precursor is then easily converted to the target compounds using known reactions,

Chiral molecular tweezers: Synthesis and reactivity in asymmetric hydrogenation

We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism pointed to the importance of both repulsive steric and stabilizing intermolecular non-covalent forces in the stereodetermining hydride transfer step of the catalytic cycle.