Ketamine Hydrochloride

Base Information

• Chemical Name: Ketamine Hydrochloride
• CAS No.: 1867-66-9
• Deprecated CAS: 42551-62-2,81771-21-3,96448-41-8,79499-52-8,100477-73-4
• Molecular Formula: C13H16ClNO.ClH
• Molecular Weight: 274.19
• Hs Code.: 2923900100
• European Community (EC) Number: 217-484-6
• NSC Number: 116131
• UNII: O18YUO0I83
• DSSTox Substance ID: DTXSID4040137
• Wikidata: Q27105184
• NCI Thesaurus Code: C29142
• RXCUI: 203184
• ChEMBL ID: CHEMBL1714
• Mol file: 1867-66-9.mol

Synonyms:2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone;Calipsol;Calypsol;CI 581;CI-581;CI581;Kalipsol;Ketalar;Ketamine;Ketamine Hydrochloride;Ketanest;Ketaset

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Ketamine Hydrochloride

Chemical Property:

• Appearance/Colour: white
• Vapor Pressure: 1.76E-05mmHg at 25°C
• Melting Point: 252-254°C
• Boiling Point: 363.8°C at 760 mmHg
• PKA: 7.5(at 25℃)
• Flash Point: 173.8°C
• PSA: 29.10000
• Density: 1.17g/cm3
• LogP: 4.09070
• Storage Temp.: 2-8°C
• Solubility.: H2O: 200 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 273.0687196
• Heavy Atom Count: 17
• Complexity: 269

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl.Cl
• Recent ClinicalTrials: Ketamine and Magnesium in Erector Spinae Plane Block
• Recent EU Clinical Trials: Analgesic Efficacy and Pharmacokinetic-pharmacodynamic Relationship of Intranasally Administered Sufentanil, Ketamine, and CT001 after Impacted Mandibular Third Molar Extraction
• Recent NIPH Clinical Trials: Ketamine administration for treatment-resistant depression
• Uses: Anesthetic (intravenous). Controlled substance (depressant).
• Therapeutic Function: Anesthetic
• Biological Functions: Ketamine is a cyclohexanone derivative whose pharmacological actions are quite different from those of the other IV anesthetics. The state of unconsciousness it produces is trancelike (i.e., eyes may remain open until deep anesthesia is obtained) and cataleptic; it has frequently been characterized as dissociative (i.e., the patient may appear awake and reactive but does not respond to sensory stimuli). The term dissociative anesthesia is used to describe these qualities of profound analgesia, amnesia, and superficial level of sleep.
• Clinical Use: Like other dissociative anesthetics, ketamine isabused for its hallucinatory effects. Most of the illegallyused ketamine comes from stolen legitimate sources, particularlyfrom veterinary clinics or smuggled in fromMexico.Ketamine is metabolized via N-demethylation to formthe main metabolite norketamine. Norketamine has aboutone third the potency of the parent compound. Minor metabolicpathways include hydroxylation of the cyclohexanonering; hydroxylation followed by glucuronide conjugation,and hydroxylation followed by dehydration to the cyclohexenonederivative.
• Drug interactions: Molecular weight (daltons) 274.2 (as hydrochloride) % Protein binding 20-50 % Excreted unchanged in urine 2 (88% as metabolites) Volume of distribution (L/kg) 4 Half-life - normal/ESRF (hrs) 2-4 / Unchanged

Technology Process of Ketamine Hydrochloride

There total 8 articles about Ketamine Hydrochloride 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: 93.6%

1-((2-chlorophenyl)(methylimino)methyl)cyclopentanol hydrochloride → (+/-)-ketamine hydrochloride (1867-66-9)

Guidance literature:

With aluminum (III) chloride; benzoic acid ethyl ester; at 125 ℃; for 5h; Temperature; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00553

Reference yield: 70.0%

1-((2-chlorophenyl)(methylimino)methyl)cyclopentan-1-ol (6740-87-0) → (+/-)-ketamine hydrochloride (1867-66-9)

Guidance literature:

With hydrogenchloride; In ethanol; at 175 ℃; for 0.0833333h; under 12929 Torr; Solvent; Temperature; Pressure; Flow reactor;

Reference yield:

(2-chlorophenyl)(cyclopentyl)methanone (6740-85-8) → (+/-)-ketamine hydrochloride (1867-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide; oxygen; triethyl phosphite / ethanol / 0.08 h / 25 °C / 8250.83 Torr / Flow reactor

2: Triisopropyl borate / ethanol / 0.02 h / 60 °C / 3900.39 Torr / Flow reactor

3: montmorillonite K₁₀ Clay; hydrogenchloride / ethanol / 180 °C / 26252.6 Torr / Flow reactor

With hydrogenchloride; Triisopropyl borate; montmorillonite K₁₀ Clay; oxygen; potassium hydroxide; triethyl phosphite; In ethanol;

DOI:10.1039/c9gc00336c

upstream raw materials:

(2-chlorophenyl)(cyclopentyl)methanone

2-Chlorobenzonitrile

(±)-(2-chlorophenyl)(1-hydroxycyclopentyl)methanone

1-((2-chlorophenyl)(methylimino)methyl)cyclopentan-1-ol

Downstream raw materials:

DL-N-Nitrosoketamin

Refernces

• 1、 Kassin, Victor-Emmanuel H.,Gérardy, Romaric,Toupy, Thomas,Collin, DIégo,Salvadeo, Elena,Toussaint, Fran?ois,Van Hecke, Kristof,Monbaliu, Jean-Christophe M.. "Expedient preparation of active pharmaceutical ingredient ketamine under sustainable continuous flow conditions". . p. 2952 - 2966. Retrieved 2019/06/18.
• 2、 -. "Method for inducing crystalline state transition in medicinal substance". . . Retrieved 2008/06/13.