34104-67-1

Basic information

• Product Name: HALOPERIDOL METABOLITE II
• Synonyms: (±)-4-(4-chlorophenyl)-α-(4-fluorophenyl)-4-hydroxy-1-piperidinebutanol;4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanol;136271-60-8 (.alpha.R);136271-61-9 (.alpha.S);1-Piperidinebutanol, 4-(4-chlorophenyl)-.alpha.-(4-fluorophenyl)-4-hydroxy-(R/S);Aids001752;Aids-001752;Hydroxy-haloperidol
• CAS NO: 34104-67-1
• Molecular Formula: C₂₁H₂₅ClFNO₂
• Molecular Weight: 377.884
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 34104-67-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 125-127°C
• Boiling Point: 531.2°C at 760 mmHg
• Flash Point: 275.1°C
• Appearance: white/
• Density: 1.247g/cm³
• Vapor Pressure: 4.08E-12mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: Refrigerator
• Solubility: DMSO: soluble10mg/mL
• CAS DataBase Reference: HALOPERIDOL METABOLITE II(CAS DataBase Reference)
• NIST Chemistry Reference: HALOPERIDOL METABOLITE II(34104-67-1)
• EPA Substance Registry System: HALOPERIDOL METABOLITE II(34104-67-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 34104-67-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Haloperidol Metabolite II

InChI:InChI=1/C21H25ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,20,25-26H,1-2,11-15H2

Upstream product

• 52-86-8 haloperidol 
• 34104-51-3 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)-4-oxobutan-1-one 
• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 51787-87-2 (+/-)-4-chloro-1-(4-fluorophenyl)butan-1-ol 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 235109-63-4 4-(4-chloro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 106-39-8 bromochlorobenzene 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 

Downstream Products

• 154440-77-4 RHPP+ 
• 52-86-8 haloperidol 

Relevant articles and documents

Dual Sigma-1 receptor antagonists and hydrogen sulfide-releasing compounds for pain treatment: Design, synthesis, and pharmacological evaluation

The development of σ1 receptor antagonists hybridized with a H2S-donor is here reported. We aimed to obtain improved analgesic effects when compared to σ1 receptor antagonists or H2S-donors alone. In an in vivo

Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells

(±)-MRJF22 [(±)-2], a novel prodrug of haloperidol metabolite II (sigma-1 receptor antagonist/sigma-2 receptor agonist ligand) obtained by conjugation to valproic acid (histone deacetylase inhibitor) via an ester bond, exhibits antiangiogenic activity, being able to reduce human retinal endothelial cell (HREC) viability in a comparable manner to bevacizumab. Moreover, (±)-2 was able to significantly reduce viable cells count, endothelial cell migration, and tube formation in vascular endothelial growth factor A (VEGF-A) stimulated HREC cultures.

Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds

3-Hydroxyhexobarbital dehydrogenase (3HBD) catalyzes NAD(P) +-linked oxidation of 3-hydroxyhexobarbital into 3-oxohexobarbital. The enzyme has been thought to act as a dehydrogenase for xenobiotic alcohols and some hydroxysteroids, but its physiological function remains unknown. We have purified rabbit 3HBD, isolated its cDNA, and examined its specificity for coenzymes and substrates, reaction directionality and tissue distribution. 3HBD is a member (AKR1C29) of the aldo-keto reductase (AKR) superfamily, and exhibited high preference for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D2, which were converted to 3α-, 17β- and 20α-hydroxysteroids and 9α,11β- prostaglandin F2, respectively. Especially, α-diketones (such as isatin and diacetyl) and lipid peroxidation-derived aldehydes (such as 4-oxo- and 4-hydroxy-2-nonenals) were excellent substrates showing low Km values (0.1-5.9 μM). In 3HBD-overexpressed cells, 3-oxohexobarbital and 5β-androstan-3α-ol-17-one were metabolized into 3-hydroxyhexobarbital and 5β-androstane-3α,17β-diol, respectively, but the reverse reactions did not proceed. The overexpression of the enzyme in the cells decreased the cytotoxicity of 4-oxo-2-nonenal. The mRNA for 3HBD was ubiquitously expressed in rabbit tissues. The results suggest that 3HBD is an NADPH-preferring reductase, and plays roles in the metabolisms of steroids, prostaglandin D2, carbohydrates and xenobiotics, as well as a defense system, protecting against reactive carbonyl compounds.