120199-64-6

Basic information

• Product Name: Cyclohexanone,2-amino-2-(2-chlorophenyl)-6-hydroxy-,(2R-cis)-(9Cl)
• Synonyms: Cyclohexanone,2-amino-2-(2-chlorophenyl)-6-hydroxy-,(2R-cis)-(9Cl);(2R,6R)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone
• CAS NO: 120199-64-6
• Molecular Formula: C12H14ClNO2
• Molecular Weight: 239.7
• EINECS: -0
• Mol File: 120199-64-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 423.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.316±0.06 g/cm3(Predicted)
• PKA: 12.59±0.40(Predicted)
• CAS DataBase Reference: Cyclohexanone,2-amino-2-(2-chlorophenyl)-6-hydroxy-,(2R-cis)-(9Cl)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone,2-amino-2-(2-chlorophenyl)-6-hydroxy-,(2R-cis)-(9Cl)(120199-64-6)
• EPA Substance Registry System: Cyclohexanone,2-amino-2-(2-chlorophenyl)-6-hydroxy-,(2R-cis)-(9Cl)(120199-64-6)

Safety Data

• Hazardous Substances Data: 120199-64-6(Hazardous Substances Data)

Upstream product

• 6740-88-1 ketamine 
• 35211-10-0 norketamine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 108-94-1 cyclohexanone 
• 91767-28-1 1-(2-chlorophenyl)-cyclohexane-1-ol 
• 17465-36-0 2'-chloro-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 103904-69-4 2-(o-chlorophenyl)-2-<(methoxycarbonyl)amino>cyclohexanone 
• 103933-03-5 methyl (2'-chloro-6-((trimethylsilyl)oxy)-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1-yl)carbamate 
• 79499-57-3 (±)-1-((2-chlorophenyl)(imino)methyl)cyclopentan-1-ol 
• 873-32-5 2-Chlorobenzonitrile 
• 6740-85-8 (2-chlorophenyl)(cyclopentyl)methanone 
• 6740-86-9 (1-Bromocyclopentyl)(2-chlorophenyl)methanone 
• 103904-71-8 [(1S,3S)-1-(2-Chloro-phenyl)-2-oxo-3-trimethylsilanyloxy-cyclohexyl]-carbamic acid methyl ester 
• 103904-70-7 2-(o-chlorophenyl)-2-<(methoxycarbonyl)amino>-6-hydroxycyclohexanone 

Relevant articles and documents

Enzyme-Mediated Two-Step Regio- And Stereoselective Synthesis of Potential Rapid-Acting Antidepressant (2 S,6 S)-Hydroxynorketamine

Recently, the anesthetic (S)-ketamine has been approved as a rapid-acting and long-lasting antidepressant. Its metabolite, (2S,6S)-hydroxynorketamine, has been found to have a similar antidepressant effect but with less undesirable side effects, which make this compound an interesting target for synthesis. Using the first-sphere mutagenesis of the cytochrome P450 154E1 from Thermobifida fusca YX, we constructed a triple mutant that enables the effective production of (2S,6S)-hydroxynorketamine from (S)-ketamine. This engineered P450 monooxygenase catalyzes the consecutive oxidative N-demethylation and highly regio- and stereoselective C6-hydroxylation reactions leading directly to the desired product with 85% product selectivity. The integration of this selective monooxygenase into an Escherichia coli whole-cell biocatalyst allowed the production of (2S,6S)-hydroxynorketamine at a semipreparative scale. The metabolite was purified and its structure was confirmed by NMR spectroscopy.

LONG-ACTING LOW-ADDICTION HNK DERIVATIVE AND PREPARATION METHOD THEREFOR

The present application relates to a compound having the functions of being an antidepressant, improving anxiety and post-traumatic stress syndrome, anesthetizing, easing pain, improving cognitive function, protecting the lungs, preventing or treating amyotrophic lateral sclerosis or preventing or treating complex regional pain syndrome. Compared with existing known HNK compounds, the compound of the present invention has a longer drug efficacy period, and the compound of the present invention essentially does not lead to addiction.

CRYSTAL FORMS AND METHODS OF SYNTHESIS OF (2R, 6R)-HYDROXYNORKETAMINE AND (2S, 6S)-HYDROXYNORKETAMINE

The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketamine (HNK) includes preparation of (R)-norketamine via chiral resolution from racemic norketamine via a chiral resolution with L-pyroglutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine hydrochloride salts.