77-10-1

Basic information

• Product Name: PHENCYCLIDINE
• Synonyms: HUMPCP;PrCP active human;prolylcarboxypeptidase;PCP;PHENCYCLIDINE;1-(1-PHENYLCYCLOHEXYL)PIPERIDINE;Pcp (phencyclidine);Phencyclidine (pcp)
• CAS NO: 77-10-1
• Molecular Formula: C₁₇H₂₅N
• Molecular Weight: 243.39
• Mol File: 77-10-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 46.5℃
• Boiling Point: bp1.0 135-137°
• Flash Point: 11 °C
• Appearance: /
• Density: 0.9762 (rough estimate)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: −20°C
• PKA: pKa 8.5 (Uncertain)
• CAS DataBase Reference: PHENCYCLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENCYCLIDINE(77-10-1)
• EPA Substance Registry System: PHENCYCLIDINE(77-10-1)

Safety Data

• Hazard Codes: F,T
• Statements: 23/24/25-39/23/24/25-11-61
• Safety Statements: 36/37-45-16-53
• RIDADR: 2811
• WGK Germany: 1
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 77-10-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.

Brand name

Sernylan (Parke-Davis).

General Description

Phencyclidine was introduced as a dissociative anestheticfor animals. Its close structural relative ketamine is still soused and may be used in humans. In humans,PCP produces a sense of intoxication, hallucinogenic experiencesnot unlike those produced by the anticholinergic hallucinogens,and often, amnesia.The drug affects many systems, including those of NE,DA, and 5-HT. It has been proposed that PCP (and certainother psychotomimetics) produces a unique pattern of activationof ventral tegumental area dopaminergic neurons.Itblocks glutaminergic N-methyl-D-aspartate receptors.Thisaction is the basis for many of its CNS effects. PCP itself appearsto be the active agent. The psychotic state produced bythis drug is also cited as a better model than amphetaminepsychosis for the psychotic state of schizophrenia.

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

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

Downstream Products

• 76916-11-5 3,3'-Bis<1-(1-piperidyl)cyclohexyl>azobenzene 
• 76916-10-4 4,4'-bis<1-(1-piperidyl)cyclohexyl>azobenzene 
• 76916-16-0 1-Phenyl-3-[3-(1-piperidin-1-yl-cyclohexyl)-phenyl]-thiourea 
• 72242-00-3 3-aminophencyclidine 
• 120807-79-6 1-(1-Phenyl-cyclohexyl)-3-trimethylsilanyloxy-piperidine 
• 123041-84-9 1-(1-phenlcyclohexyl)-3-piperidine 
• 77160-80-6 methyl 5-pentanoate 
• 120807-75-2 1-(1-Phenyl-4-trimethylsilanyloxy-cyclohexyl)-piperidine 
• 120807-81-0 1-(1-Phenyl-cyclohexyl)-4-trimethylsilanyloxy-piperidine 
• 2201-34-5 1-[1-(2-methoxy-phenyl)-cyclohexyl]-piperidine 
• 100-42-5 styrene 
• 91-20-3 naphthalene 
• 92-52-4 biphenyl 
• 85-01-8 phenanthrene 

Relevant articles and documents

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 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 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.