60232-85-1

Basic information

• Product Name: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine
• Synonyms: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine;1-(1-Phenylcyclohexyl)piperidine-4-ol;4-Hydroxy Phencyclidine;4-Hydroxy-1-(1-phenylcyclohexyl)piperidine;4-Hydroxyphencyclidine;N-(1-Phenylcyclohexyl)-4-hydroxypiperidine;NSC 170516;1-(1-phenylcyclohexyl)piperidin-4-ol
• CAS NO: 60232-85-1
• Molecular Formula: C₁₇H₂₅NO
• Molecular Weight: 259.39
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 60232-85-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 116-118 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• Boiling Point: 400.9°C at 760 mmHg
• Flash Point: 106.1°C
• Appearance: /
• Density: 1.093g/cm³
• Vapor Pressure: 3.79E-07mmHg at 25°C
• Refractive Index: 1.574
• PKA: 14.86±0.20(Predicted)
• CAS DataBase Reference: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine(60232-85-1)
• EPA Substance Registry System: 1-(1-phenylcyclohexyl)-4-hydroxypiperidine(60232-85-1)

Safety Data

• Hazardous Substances Data: 60232-85-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Research:
1-(1-phenylcyclohexyl)-4-hydroxypiperidine is used as a research compound for understanding the effects and mechanisms of action of Phencyclidine (PCP) and its metabolites. Its PCP-like stimuli make it a valuable tool in studying the neurological and psychoactive properties of PCP, which can contribute to the development of new therapeutic strategies for related conditions.
2. Used in Toxicology and Drug Metabolism Studies:
As a metabolite of Phencyclidine, 1-(1-phenylcyclohexyl)-4-hydroxypiperidine is utilized in toxicology and drug metabolism research. It helps scientists investigate the metabolic pathways and toxic effects of PCP, which can be crucial for assessing the risks and safety profiles of similar compounds.
3. Used in Drug Development:
1-(1-phenylcyclohexyl)-4-hydroxypiperidine may also be used in the development of new drugs with similar structures or mechanisms of action. By studying the properties and effects of 1-(1-phenylcyclohexyl)-4-hydroxypiperidine, researchers can gain insights into designing more effective and safer medications for various applications.
4. Used in Analytical Chemistry:
1-(1-phenylcyclohexyl)-4-hydroxypiperidine can be employed as a reference material or standard in analytical chemistry, particularly in the development and validation of analytical methods for the detection and quantification of PCP and its metabolites in biological samples.
5. Used in Forensic Science:
In forensic science, the compound can be used for the identification and analysis of PCP and its metabolites in cases involving drug-related crimes or toxicological investigations.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 24, p. 496, 1981 DOI: 10.1021/jm00137a004

InChI:InChI=1/C17H25NO/c19-16-9-13-18(14-10-16)17(11-5-2-6-12-17)15-7-3-1-4-8-15/h1,3-4,7-8,16,19H,2,5-6,9-14H2

Upstream product

• 108-86-1 bromobenzene 
• 344260-33-9 1-(4-Trimethylsilanyloxy-piperidin-1-yl)-cyclohexanecarbonitrile 
• 77-10-1 Phencyclidine 
• 956-90-1 phencyclidine hydrochloride 
• 60756-86-7 4-hydroxypiperidinocyclohexyl carbonitrile 
• 108-94-1 cyclohexanone 
• 5382-17-2 piperidin-4-ol hydrochloride 
• 106-93-4 ethylene dibromide 

Downstream Products

• 77179-35-2 Benzoic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester 
• 77179-38-5 1-(1-phenylcyclohexyl)-4-piperidyl acetate 
• 77179-34-1 3,4-Dimethoxy-benzoic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester 
• 77179-39-6 1-(1-phenylcyclohexyl)-4-phenyl-4-piperidinol 
• 77179-40-9 1-(1-phenylcyclohexyl)-4-phenyl-4-piperidyl propionate 
• 77179-42-1 1-(1-phenylcyclohexyl)-4-piperidone 
• 77179-37-4 4-Amino-benzoic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester 
• 120807-81-0 1-(1-Phenyl-cyclohexyl)-4-trimethylsilanyloxy-piperidine 
• 77179-36-3 Nicotinic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester 

Relevant articles and documents

Metabolism of phencyclidine by microorganisms

A number of microorganisms were screened for their ability to metabolize phencyclidine. Two microorganisms, Beauveria sulfurescens and Cunninghamella echinulata, produced hydroxylated metabolites, which were identified as 1-(1-phenylcyclohexyl)-4-hydroxypiperidine and 4-phenyl-4-piperidinocyclohexanol by high-pressure liquid chromatographic analysis.

Synthesis and analgesic activity of new phencyclidine derivatives

New phencyclidine derivatives having structural similarities with the well known 4-phenylpiperidine narcotic analgesics were synthesized, characterized and their anti-nociceptive activity tested in mice by the hot-plate and tail-flick tests. Structure, activity relationships for these compounds further point to the importance of a second aryl moiety at position 4 of the piperidine ring of phencyclidine. In addition, the presence of a hydroxyl group in close proximate to the lipophilic moiety is vital for analgesic activity.

Phencyclidine and phencyclidine metabolites assay, tracers, immunogens and antibodies

The present invention is directed to a fluorescence polarization assay for phencyclidine and phencyclidine derivatives, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for making them. The tracers and the immunogens are made from substituted phencyclidine compounds. A fluorescein moiety is included in the tracer, while a poly(amino acid) forms a part of the immunogen. The assay is conducted by measuring the degree of polarization retention of plane polarized light that has been passed through a sample containing antiserum and tracer.

New Analgesic Drugs Derived from Phencyclidine

Several esters of 1-(1-phenylcyclohexyl)-4-piperidinol (3), 1-(1-phenylcyclohexyl)-4-phenyl-4-piperidinol (10) and its propionate (11), and 1-(1-phenylcyclohexyl)-4-phenylpiperidine (13) were prepared and characterized.The new compounds, which are derived from phencyclidine, exerted analgesic activity in mice.The most potent is 10, which is twice as active as morphine.The antinociceptive activity of 10, 11, and 13 could be well correlated with their potency in the mouse vas deferens bioassay, and both were completely reversed by naloxone.