4-Hydroxyalprazolam

Base Information

• Chemical Name: 4-Hydroxyalprazolam
• CAS No.: 30896-57-2
• Deprecated CAS: 144147-12-6
• Molecular Formula: C17H13 Cl N4 O
• Molecular Weight: 324.769
• Hs Code.: 2933990090
• UNII: U0COM4319X
• DSSTox Substance ID: DTXSID90932240
• Nikkaji Number: J807.558A
• Wikidata: Q27290520
• ChEMBL ID: CHEMBL1313
• Mol file: 30896-57-2.mol

Synonyms:4-hydroxyalprazolam

Chemical Property of 4-Hydroxyalprazolam

Chemical Property:

• Vapor Pressure: 2.42E-13mmHg at 25°C
• Melting Point: 160-162oC
• Boiling Point: 559.2°Cat760mmHg
• PKA: 11.59±0.40(Predicted)
• Flash Point: 292°C
• PSA: 63.30000
• Density: 1.45g/cm³
• LogP: 2.50660
• Storage Temp.: Controlled Substance, -20?C Freezer
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 324.0777887
• Heavy Atom Count: 23
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-Alprazolam-d5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2O)C4=CC=CC=C4
• Description: Alprazolam is a benzodiazepine with anxiolytic and sedative actions. 4-Hydroxyalprazolam is a major metabolite of alprazolam, produced by the actions of cytochrome P450 (CYP) isoforms CYP3A4 and CYP3A5. It may be detected in serum or, in a glucuronidated form, in urine. Alternatively, 4-hydroxyalprazolam can be further metabolized to benzophenone.
• Uses: A metabolite of Alprazolam, a benzodiazepine. Controlled Substance

Technology Process of 4-Hydroxyalprazolam

There total 7 articles about 4-Hydroxyalprazolam 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: 84.7%

8-chloro-4-hydroxy-1-methyl-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepine acetate (30896-67-4) → 4-Hydroxyalprazolam (30896-57-2,144147-12-6)

Guidance literature:

With sodium hydroxide; In ethanol; for 1h;

DOI:10.1021/jm00180a012

Reference yield: 51.0%

4-(2-benzoyl-4-chlorophenyl)-5-methyl-4H-1,2,4-triazole-3-carboxaldehyde (36916-20-8) → 4-Hydroxyalprazolam (30896-57-2,144147-12-6)

Guidance literature:

With ammonia; In ethanol; for 5h; Ambient temperature;

DOI:10.1021/jm00180a012

Reference yield:

10-chloro-6-methyl-11b-phenyl-3H,11bH-oxazirino<3,2-d>-s-triazolo<4,3-a><1,4>benzodiazepine (36916-14-0) → 4-Hydroxyalprazolam (30896-57-2,144147-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 15.7 percent / 1,3,5-trimethyl-benzene / 0.25 h / Heating

2: 36 percent / AcOH / 0.5 h / Heating

3: 84.7 percent / 1N NaOH / aq. ethanol / 1 h

With sodium hydroxide; acetic acid; In ethanol; 1,3,5-trimethyl-benzene;

DOI:10.1021/jm00180a012

upstream raw materials:

8-chloro-4-hydroxy-1-methyl-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepine acetate

4-(2-benzoyl-4-chlorophenyl)-5-methyl-4H-1,2,4-triazole-3-carboxaldehyde

alprazolam

8-chloro-1-methyl-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepine 5-oxide

Downstream raw materials:

4-fluoro-8-chloro-1-methyl-6-phenyl-4H-5-triazolo<4.3.a>-<1,4>benzodiazepine

8-chloro-5,6-dihydro-1-methyl-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepin-4-one

8-chloro-4-hydroxy-1-methyl-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepine acetate