(R)-Ketamine

Base Information

• Chemical Name: (R)-Ketamine
• CAS No.: 33643-49-1
• Molecular Formula: C₁₃H₁₆ClNO
• Molecular Weight: 237.729
• UNII: Y2RI13H7VW
• DSSTox Substance ID: DTXSID2048747
• Nikkaji Number: J238.629A
• Wikipedia: Arketamine
• Wikidata: Q20707684
• Metabolomics Workbench ID: 67023
• ChEMBL ID: CHEMBL467505
• Mol file: 33643-49-1.mol

Synonyms:(R)-Ketamine;arketamine;(+)-Ketamine;d-Ketamine;(R)-(+)-Ketamine;33643-49-1;Ketamine, R-;Ketamine, (R)-;Y2RI13H7VW;UNII-Y2RI13H7VW;J238.629A;(2R)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one;DTXSID2048747;CHEBI:580604;(2R)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone;cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2R)-;(2R)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone;Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+)-;(S) Ketamine;ARKETAMINE [WHO-DD];SCHEMBL16104;CHEMBL467505;GTPL9153;DTXCID9028673;PCN-101;Tox21_113205;NCGC00185909-01;CAS-33643-49-1;HR-071603;Q20707684;(2R)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one;Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (R)-;Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2R)- (9CI);Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+)- (8CI);RKE

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Chemical Property of (R)-Ketamine

Chemical Property:

• Vapor Pressure: 1.76E-05mmHg at 25°C
• Boiling Point: 363.8°Cat760mmHg
• PKA: 6.46±0.20(Predicted)
• Flash Point: 173.8°C
• PSA: 29.10000
• Density: 1.17g/cm³
• LogP: 3.28870
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 237.0920418
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl
• Isomeric SMILES: CN[C@]1(CCCCC1=O)C2=CC=CC=C2Cl
• Recent ClinicalTrials: A Randomized, Placebo-Controlled, Double-Blind Study to Assess Safety and Efficacy of PCN-101 in TRD
• Recent EU Clinical Trials: A randomized, placebo-controlled, double-blind study to assess the safety and efficacy of intravenous PCN-101 in treatment-resistant depression
• Recent NIPH Clinical Trials: Effects of single intravenous arketamine dose as adjunctive therapy for bipolar depression: a randomized, double-blind, crossover, placebo-controlled trial

Technology Process of (R)-Ketamine

There total 72 articles about (R)-Ketamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(+/-)-ketamine hydrochloride (1867-66-9) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

With sodium hydroxide; In chloroform; water;

Reference yield: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + norketamine (35211-10-0,83777-65-5) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 12h;

Reference yield: 85.3%

(±)-2-(2-chlorophenyl)-2-hydroxycyclohexan-1-one + methylamine (74-89-5) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

(±)-2-(2-chlorophenyl)-2-hydroxycyclohexan-1-one; With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at -5 - 0 ℃; for 1h; Inert atmosphere;

methylamine; In ethanol; at 15 - 20 ℃;

DOI:10.1021/acs.joc.0c01090

upstream raw materials:

DL-N-Nitrosoketamin

(+/-)-ketamine hydrochloride

2-(2-chlorophenyl)-2-nitrocyclohexan-1-one

formaldehyd

Downstream raw materials:

(2S,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one

(+)-Ketamine hydrochloride

(S)-ketamine