7-Hydroxychlorpromazine

Base Information

• Chemical Name: 7-Hydroxychlorpromazine
• CAS No.: 2095-62-7
• Molecular Formula: C17H19 Cl N2 O S
• Molecular Weight: 334.86
• Hs Code.: 2934300000
• European Community (EC) Number: 803-380-3
• NSC Number: 131053
• UNII: P0X9L6UVP0
• DSSTox Substance ID: DTXSID20175128
• Nikkaji Number: J50.184K
• Wikidata: Q27216094
• Pharos Ligand ID: K9TGSTSD83BH
• ChEMBL ID: CHEMBL909
• Mol file: 2095-62-7.mol

Synonyms:7-hydroxychlorpromazine;7-hydroxychlorpromazine monohydrochloride

Chemical Property of 7-Hydroxychlorpromazine

Chemical Property:

• Vapor Pressure: 3.59E-11mmHg at 25°C
• Melting Point: 178-179℃
• Boiling Point: 513.6°C at 760 mmHg
• Flash Point: 264.4°C
• PSA: 52.01000
• Density: 1.281g/cm³
• LogP: 4.66500
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.0906621
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

97% ^*data from raw suppliers

7-Hydroxy Chlorpromazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)CCCN1C2=C(C=C(C=C2)O)SC3=C1C=C(C=C3)Cl
• Uses: 7-Hydroxychlorpromazine is the 7-hydroxy analogue and a major metabolite of the atypical antipsychotic Chlorpromazine (C424750). 7-Hydroxy-2-chloropromazine is a metabolite of chlorpromazine. Chlorpromazine exhibits antiadrenergic, antiserotonergic, anticholinergic, and antihistaminergic properties, and commonly used in the treatment of schizophrenia.

Technology Process of 7-Hydroxychlorpromazine

There total 2 articles about 7-Hydroxychlorpromazine 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: 0.4%

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3) → 7-hydroxychlorpromazine (2095-62-7) + 2-chloro-10-(3-dimethylamino-propyl)-10H-phenothiazin-1-ol (3926-66-7) + 3-hydroxyl CPZ (3930-47-0) + chlorpromazine sulfoxide (969-99-3)

Guidance literature:

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine; With ethylenediaminetetraacetic acid trisodium salt; oxygen; manganese (II) acetate tetrahydrate; ascorbic acid; In water; pH=4;

With ferrous(II) sulfate heptahydrate; ethylenediaminetetraacetic acid trisodium salt; oxygen; In water; at 45 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.12.014

Reference yield:

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3) → 7-hydroxychlorpromazine (2095-62-7) + Chlorpromazine oxide (1672-76-0) + 2-chloro-10H-phenothiazine 5-oxide (1927-43-1) + 8-chloro-10H-phenothiazin-3-ol (2002-32-6) + 2-chloro-10-(3-aminopropyl)phenothiazine (2095-17-2) + Norchlorpromazine (1225-64-5) + chlorpromazine sulfoxide (969-99-3) + N-[3-(2-chloro-phenothiazin-10-yl)-propyl]-formamide (70732-75-1) + C32H30Cl2N4S2 + Didesmethylchlorpromazine sulfoxide (2232-49-7) + Demethylchlorpromazine sulfoxide (2037-58-3)

Guidance literature:

With NADPH; In aq. buffer; at 30 ℃; pH=7.3; Enzymatic reaction;

DOI:10.1021/acs.joc.1c01407

Reference yield:

7-hydroxychlorpromazine (2095-62-7) + acetic anhydride (108-24-7) → 10-(3-Dimethylamino-propyl)-7-acetoxy-2-chlor-phenthiazin (14734-77-1)

Guidance literature:

With sodium dithionite; In acetic acid; for 4h; Heating;

upstream raw materials:

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Downstream raw materials:

10-(3-Dimethylamino-propyl)-7-acetoxy-2-chlor-phenthiazin

Refernces

• 1、 Slavik, Roger,Peters, Jens-Uwe,Giger, Rudolf,Bürkler, Markus,Bald, Eric. "Synthesis of potential drug metabolites by a modified Udenfriend reaction". experimental part. p. 749 - 752. Retrieved 2011/03/21.