77-10-1

Usage

Uses

Used in Research Applications:
Phencyclidine is utilized as a research tool for studying the mechanisms underlying schizophrenia and other psychotic disorders. Its ability to induce a psychotic state similar to that of schizophrenia makes it a valuable model for investigating the neurobiological basis of these conditions.
Used in Veterinary Medicine:
Although its use as an anesthetic has been discontinued due to its potential for abuse and adverse effects, PCP was initially developed as a dissociative anesthetic for animals. Its effects on the central nervous system made it a candidate for use in veterinary medicine, particularly for procedures requiring sedation or anesthesia in animals.
Used in Drug Development:
Phencyclidine's interaction with various neurotransmitter systems and its effects on specific neuronal pathways have made it a target for drug development. Researchers are interested in understanding its mechanisms of action to develop new therapeutic agents that can modulate these pathways for the treatment of various neurological and psychiatric disorders.
Used in Toxicology Studies:
Due to its neurotoxic effects and potential for abuse, PCP is also used in toxicology studies to investigate the harmful effects of substance abuse on the human body. These studies aim to develop strategies for prevention, treatment, and rehabilitation of individuals affected by substance abuse.

Pharmacology

PCP acts as a biocide through its ability to uncouple mitochondrial oxidative phosphorylation.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Caution: This is a controlled substance (depressant) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.12 (1985). The ethylamine, pyrrolidine and thiophene analogs are l

Metabolic pathway

When mice and rats are administered phencyclidine intraperitoneally, several hydroxylated metabolites are identified in the urine. A new metabolite, 1-phenyl-1- (1-piperidinyl-3-ol)cyclohexane, is identified in the urine and liver microsomal preparations.

Metabolism

Pentachlorophenolwas metabolized in rats by conjugation with glucuronic acid and eliminated as the glucuronide. P450 catalyzed oxidative dechlorination also occurred to form tetrachlorohydroquinone, and this was conjugated to form a monoglucuronide representing 27% of the dose administered. Other metabolites have been reported, including isomeric tetrachlorophenols, tetrachlorocatechol and tetrachlororesorcinol. Trace amounts of benzoquinones were also noted. Metabolites in female rats were tetrachloromonophenols, diphenols, and hydroquinones.

Toxicity evaluation

The toxicology has been addressed in a recent risk assessment (119). Acutely, pentachlorophenol was reported to have LD50 values in the rat of 12 mg/kg (inhalation) and 146 mg/kg (M)–175 mg/kg (F) by oral gavage. More detailed studies of the toxicology of pentachlorophenol have been compromised by the toxicity of impurities present in most of the earlier samples used in the evaluation process.

InChI:InChI=1S/C17H25N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11H,2-3,6-9,12-15H2

Upstream product

• 120802-88-2 1-(1-Piperidin-1-yl-cyclohexyl)-1H-benzotriazole 
• 110-89-4 piperidine 
• 108-94-1 cyclohexanone 
• 108-86-1 bromobenzene 
• 3867-15-0 1-piperidinocyclohexylcarbonitrile 
• 100-58-3 phenylmagnesium bromide 
• 7439-95-4 magnesium 

Downstream Products

• 79787-43-2 N-[1-(3-hydroxyphenyl)cyclohexyl]piperidine 
• 81262-67-1 1-(1-phenylcyclohexyl)-2-cyanopiperidine 
• 70227-29-1 3-nitrophencyclidine 
• 60658-01-7 4-nitrophencyclidine 
• 60232-85-1 1-(1-phenylcyclohexyl)-4-hydroxypiperidine 
• 60756-84-5 1-(4-hydroxy-1-phenyl-cyclohexyl)-piperidin-4-ol 
• 60756-83-4 4-Phenyl-4-piperidinocyclohexanol 
• 77160-83-9 5-pentanoic acid 
• 94852-59-2 3-hydroxy-1-(1-phenylcyclohexyl)piperidine 
• 66568-88-5 4-(1-Piperidin-1-yl-cyclohexyl)-phenol 
• 83400-97-9 2-(1-Piperidin-1-yl-cyclohexyl)-phenol 
• 123041-84-9 1-(1-phenlcyclohexyl)-3-piperidine 
• 93185-13-8 N-(1-phenylcycohexyl)piperidone 
• 100-42-5 styrene 

Relevant academic research and scientific papers

New amine and aromatic substituted analogues of phencyclidine: Synthesis and determination of acute and chronic pain activities

Background: Phencyclidine (PCP, I) is a synthetic drug with remarkable physiological properties. PCP and its analogues exert many pharmacological activities and interact with some neurotransmitter systems in the central nervous system like particular affinity for PCP sites in NMDA receptors or dopamine uptake blocking or even both. Aim and Objective: The following research, methyl group with electron-donating and dipole moment characters was added in different positions of phenyl ring along with the substitution of benzylamine (with many pharmacological effects) instead of piperidine ring of I to produce new compounds (II-V) of this family with more analgesic activities. Materials and Methods: Analgesic activities of these new compounds were measured by tail immersion and formalin tests for acute and chronic pains, respectively. Also, the outcomes were compared with control and PCP (10 mg/kg) groups. Results: The results indicate that compounds III, IV, and V have more acute and chronic antinociceptive effects than PCP and compound II which may be concerned with more antagonizing activities of these new painkillers for the blockage of dopamine reuptake as well as high affinity for NMDA receptors PCP binding site. Conclusion: It can be concluded that the benzylamine derivative of phencyclidine with a methyl group on the benzyl position on phenyl ring (V) is a more appropriate candidate to reduce acute and chronic (thermal and chemical) pains compared to other substituted phenyl analogs (II-IV) and PCP.

Synthesis and antinociception properties of phencyclidine derivatives with modified aromatic or cycloalkyl rings and amino group

Phencyclidine is an arylcyclohexylamine compound which has received a lot of investigative attention due to the complex spectrum of behaviours and its complicated interactions with the central nervous system. Phencyclidine administration may act as stimulant, depressant, hallucinogen, and analgesic depending on dose and tested species. In this study, new phenyl and thienyl analogues with specific affinity for the phencyclidine sites in NMDA receptors, dopamine uptake blocking, or both of them were synthesized. The acute and chronic pain properties of these compounds were studied using the tail immersion and formalin tests on mice and the results were compared with control and phencyclidine groups at a dose of 10 mg/kg. The outcomes indicated that all synthesized compounds showed better activities to decrease acute thermal and chemical, but not chronic pains. Also, these effects were more significant for phenyl (group 1) compared to thiophene (group 2) analogues, which is probably due to the higher affinity of group 1 for inhibition of dopamine reuptake compared to binding to the phencyclidine sites in NMDA receptors in this family.

Synthesis and antinociceptive behaviors of new methyl and hydroxyl derivatives of phencyclidine

Phencyclidine (I) and its derivatives show such pharmacological behaviors as analgesic, anticonsulvant, anti-anxiety and antidepressant, while interacting with central nervous system. In this study, new methyl and hydroxyl derivatives of PCP were synthesized and their antinociceptive behaviors in animals were examined by measuring the number of writhing in a writhing test of visceral pain and the pain scores in Formalin test. Compared to control and PCP groups, findings in experimental groups indicated the new synthesized analogues (compounds II, III and V, 10 mg/kg) of PCP were able to produce more analgesic effects in formalin and writhing tests, especially for compound V. It was concluded that the new synthesized derivatives of PCP could substantially and respectively diminish acute and chronic pains.

Synthesis and analgesic effects of methoxy-pyrrole derivative of phencyclidine on mice

Phencyclidine, 1-[1-phenylcyclohexyl]piperidine (PCP, I) and its derivatives have shown considerable pharmacological effects. In this work, pyrrole derivative of phencyclidine (PCP-pyrrole, 1-[1-phenylcyclohexyl]pyrrole, II) and a new derivative (1-[1-[3- methoxyphenylcyclohexyl]pyrrole, III) and their intermediates were synthesized, then the acute and chronic pains were examined on mices at 1 mg/kg dosage using tail immersion (as a model of acute thermal pain) and formalin (as a model of acute chemical and chronic pain) tests and the results were compared with phencyclidine and control (DMSO) groups. The results indicated that III produced more analgesic effects compared to II in tail immersion test and also revealed that the newly synthesized derivative (III) significantly reduced chronic pain (especially in initial of phase II) in formalin test compared to other groups.

Synthesis and analgesic effects of 1-[1-(2-methylphenyl)(cyclohexyl)]-3- piperidinol as a new derivative of phencyclidine in mice

Phencyclidine (1-(1-phenylcyclohexyl) piperidine, CAS 956-90-1, PCP, I) and its derivatives have shownmany analgesic effects. In this research, a newderivative of PCP (1-[1-(2-methylphenyl)(cyclohexyl)]-3-piperidinol, PD, II) was synthesized and its analgesic (acute and chronic pains) effects were examined on rats using tail immersion (as a model of acute thermal pain) and formalin (as a model of acute and chronic chemical pain) tests and the results are compared to PCP and control groups. The results indicated that II produces higher analgesic effects in the tail immersion test compared to the PCP and control groups, with a marked and significant increase in tail immersion latency for the doses 1, 5 and 10 mg/kg. The formalin test showed that PD (II) is not effective in acute chemical pain (phase I, 0-5 min after injection) in all doses but chronic pain (initial-phase II, 15-40 min after injection) is significantly attenuated by this compound compared to PCP and saline (control) in dosesof 5 and 10 mg/kg. It is concluded that II is effective in acute thermal (in all doses) and chronic (doses of 5 and 10 mg/kg) pains; however, it is not effective in acute chemical pain compared to PCP and control. ECV · Editio Cantor Verlag.

Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl)(tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests

Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 956-90-1, PCP, I) and ketamine (2-O-chlorophenyl-2-methylaminocyclohexan, CAS 1867-66-9, II) revealed some analgesic effects. Some of their derivatives have been synthesized for biological properties studies. Utilizing 1-tetralone as a starting material, 1-[1-(3-methylphenyl)(tetralyl)]piperidine, (PCP-CH3-tetralyl, III) was synthesized and its analgesic effects were studied on rats via tail immersion (as a model of acute thermal pain) and formalin (as a model of acute chemical and chronic pain) tests and compared with those of ketamine and PCP. The results indicated a marked anti-nociception 2-25 min after ketamine injection, but this analgesic effect lasted for 40 min following PCP-CH 3-tetralyl application in the tail immersion test. However, the data obtained from the formalin test showed that chronic pain could be significantly attenuated by ketamine, PCP and PCP-CH3-tetralyl. ECV·Editio Cantor Verlag, Aulendorf (Germany).

Synthesis and study on analgesic effects of 1-[1-(4-methylphenyl) (cyclohexyl)] 4-piperidinol and 1-[1-(4-methoxyphenyl) (cyclohexyl)] 4-piperidinol as two new phencyclidine derivatives

Phencyclidine (1-(1-phenylcyclohexyl) piperidine; CAS 956-90-1; PCP, I) has shown analgesic effects. Some of its derivatives have been synthesized and their biological properties have been studied. In this work, new methyl and methoxy hydroxyl derivatives of phencyclidine were synthesized and the analgesic effects of this compounds [(1-[1-(4-methylphenyl) (cyclohexyl)] 4-piperidinol, II), (1-[1-(4-methoxyphenyl) (cyclohexyl)] 4-piperidinol, III)] were studied using tail immersion test on rats and compared to PCP. The results showed that, II can produce more analgesic effects in the tail immersion test (as a model of acute thermal pain) in comparison to the PCP with a marked significant increase in tail immersion latency (15, 40 and 45 min after injection) but for III, only slight analgesic effects (15, 35 and 40 min after injection) was seen (without significant differences between pain thresholds). ECV Editio Cantor Verlag.

1,2,3-Triazole as a safer and practical substitute for cyanide in the Bruylants reaction for the synthesis of tertiary amines containing tertiary alkyl or aryl groups

Tertiary amines containing tertiary alkyl or aryl groups were synthesized by the reaction of a ketone with an amine and 1,2,3-triazole followed by substitution of the triazole adduct with a Grignard reagent. Thus, 1,2,3-triazole serves as a safer and practical alternative to cyanide in the Bruylants reaction.

[2.2] paracyclophane and derivatives thereof

Processes are disclosed for preparing [2.2] paracyclophane and derivatives thereof by conducting the Hofmann elimination of p-methylbenzyltrimethylammonium hydroxide, or derivatives thereof, in the presence of an effective amount of oxygen to inhibit the formation of by-product polymers. The oxygen can be introduced, for example, by a purge gas stream containing molecular oxygen. Products produced by the processes are also disclosed.

Non-competitive NMDA receptor antagonists and methods for their use

The present invention relates to novel NMDA receptor antagonists and methods for their use. The present invention also provided pharmaceutical compositions comprising such NMDA receptor antagonists.