(R)-Norketamine

Base Information

• Chemical Name: (R)-Norketamine
• CAS No.: 83777-64-4
• Molecular Formula: C12H14ClNO
• Molecular Weight: 223.702
• UNII: P3C0O5X442
• DSSTox Substance ID: DTXSID50435686
• Nikkaji Number: J876.135C
• Wikidata: Q27286080
• ChEMBL ID: CHEMBL467504
• Mol file: 83777-64-4.mol

Synonyms:(R)-Norketamine;83777-64-4;Norketamine, (R)-;(+)-Norketamine;(2R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one;Cyclohexanone, 2-amino-2-(2-chlorophenyl)-, (2R)-;N-Demethyl-(R)-(+)-ketamine;P3C0O5X442;J876.135C;(R)-Norketamine (hydrochloride);(R)-2-amino-2-(2-chlorophenyl)cyclohexanone;UNII-P3C0O5X442;CHEMBL467504;SCHEMBL12601750;DTXSID50435686;W13323;(R)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one;Q27286080

Chemical Property of (R)-Norketamine

Chemical Property:

• Boiling Point: 368.6±42.0 °C(Predicted)
• PKA: 6.25±0.20(Predicted)
• PSA: 43.09000
• Density: 1.208±0.06 g/cm3(Predicted)
• LogP: 3.33740
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 223.0763918
• Heavy Atom Count: 15
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(=O)C1)(C2=CC=CC=C2Cl)N
• Isomeric SMILES: C1CC[C@](C(=O)C1)(C2=CC=CC=C2Cl)N
• Uses: R-(+)-Norketamine is the main metabolite of ketamine (K165300) and is also a non-competitive NMDA receptor antagonist found in the rat cortex and spinal cord models.

Technology Process of (R)-Norketamine

There total 17 articles about (R)-Norketamine 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%

(R)-2-azido-2-(2-chlorophenyl)cyclohexan-1-one → (R)-Norketamine (83777-64-4,83777-65-5)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; water; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02498

Reference yield: 91.8%

R-norketamine (L)-pyroglutamate → (R)-Norketamine (83777-64-4,83777-65-5)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate;

DOI:10.1021/acs.orglett.7b02177

Reference yield:

(+)-Ketamine (100477-72-3,33643-46-8,33643-49-1) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-Norketamine (83777-64-4,83777-65-5)

Guidance literature:

With glucose-6-phosphate; magnesium chloride; In aq. phosphate buffer; pH=7.4; Kinetics; Enzymatic reaction;

DOI:10.1021/acs.molpharmaceut.8b01214

upstream raw materials:

(2-chlorophenyl)(cyclopentyl)methanone

(1-Bromocyclopentyl)(2-chlorophenyl)methanone

(±)-1-((2-chlorophenyl)(imino)methyl)cyclopentan-1-ol

norketamine

Downstream raw materials:

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

Refernces

• 1、 Da Silva Gomes, Roberto,Corey. "A Method for the Catalytic Enantioselective Synthesis of Chiral α-Azido and α-Amino Ketones from Racemic α-Bromo Ketones, and Its Generalization to the Formation of Bonds to C, O, and S". supporting information. p. 20058 - 20061. Retrieved 2019/12/27.
• 2、 -. "PROCESS FOR SYNTHESIS AND PURIFICATION OF (2R,6R)-HYDROXYNORKETAMINE". . . Retrieved 2019/12/28.