PCHP

Last updated
PCHP
1-(1-phenylcyclohexyl)-4-hydroxypiperidine.png
Names
Preferred IUPAC name
1-(1-Phenylcyclohexyl)piperidin-4-ol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/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 Yes check.svgY
    Key: SLUMSLWGPLFKGY-UHFFFAOYSA-N Yes check.svgY
  • 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
    Key: SLUMSLWGPLFKGY-UHFFFAOYAA
  • OC3CCN(C2(c1ccccc1)CCCCC2)CC3
Properties
C17H25NO
Molar mass 259.393 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-(1-Phenylcyclohexyl)-4-hydroxypiperidine (PCHP) is a metabolite of phencyclidine (PCP). [1] PCHP can be detected in the hair, urine, stool, sweat, and saliva of PCP users. [2]

See also

Related Research Articles

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<span class="mw-page-title-main">4-Phenyl-4-(1-piperidinyl)cyclohexanol</span> Chemical compound

4-Phenyl-4-(1-piperidinyl)cyclohexanol, also known as PPC, is an organic chemical which is a metabolite of phencyclidine (PCP). It can be detected in the hair of PCP users.

<span class="mw-page-title-main">PCAA</span> Metabolite of phencyclidine (PCP)

PCAA, or 5-[N-(1-phenylcyclohexyl)amino]pentanoic acid, is a metabolite of phencyclidine (PCP). It can be detected in the urine of PCP users by mass spectrometry as means of drug screening.

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<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce is referred to as dissociative anesthesia.

<span class="mw-page-title-main">Rolicyclidine</span> Chemical compound

Rolicyclidine (PCPy) is a dissociative anesthetic that is similar in effects to phencyclidine, but is slightly less potent and has fewer stimulant effects. It instead produces a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects. Due to its similarity in effects to PCP, PCPy was placed into the Schedule I list of illegal drugs in the 1970s, although it has never been widely abused and is now little known.

<span class="mw-page-title-main">Eticyclidine</span> Medication

Eticyclidine is a dissociative anesthetic drug with hallucinogenic effects. It is similar in effects to phencyclidine but is slightly more potent. PCE was developed by Parke-Davis in the 1970s and evaluated for anesthetic potential under the code name CI-400, but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties. PCE is slightly more potent than PCP and has similar effects, but its unpleasant taste and tendency to cause nausea made it less accepted by users. Due to its similarity in effects to PCP, PCE was placed into the Schedule 1 list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known.

<span class="mw-page-title-main">Tenocyclidine</span> Chemical compound

Tenocyclidine (TCP) is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s. It is similar in effects to phencyclidine (PCP) but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for the NMDA receptors, but less affinity for the sigma receptors. Because of its high affinity for the PCP site of the NMDA receptor complex, the 3H radiolabelled form of TCP is widely used in research into NMDA receptors.

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<span class="mw-page-title-main">Benocyclidine</span> Chemical compound

Benocyclidine, also known as benzo​thiophenyl​cyclo​hexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.

<span class="mw-page-title-main">Dieticyclidine</span> Chemical compound

Dieticyclidine (PCDE), or diethylphenylcyclohexylamine, is a psychoactive drug and research chemical of the arylcyclohexylamine chemical class related to phencyclidine (PCP) and eticyclidine (PCE). It acts as an NMDA receptor antagonist but has low potency and acts mainly as a prodrug for eticyclidine.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<span class="mw-page-title-main">3-MeO-PCP</span> Chemical compound

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

<span class="mw-page-title-main">Metaphit</span> Chemical compound

Metaphit is a research chemical that acts as an acylator of NMDARAn, sigma and DAT binding sites in the CNS. It is the m-isothiocyanate derivative of phencyclidine (PCP) and binds irreversibly to the PCP binding site on the NMDA receptor complex. However, later studies suggest the functionality of metaphit is mediated by sites not involved in PCP-induced passive avoidance deficit, and not related to the NMDA receptor complex. Metaphit was also shown to prevent d-amphetamine induced hyperactivity, while significantly depleting dopamine content in the nucleus accumbens. Metaphit was the first acylating ligand used to study the cocaine receptor. It is a structural isomer of the similar research compound fourphit, as it and metaphit both are isothiocyanate substituted derivatives of an analogous scaffold shared with PCP.

α-Endopsychosin is an antagonist of the phencyclidine site of the NMDA receptor which was discovered in extracts of porcine brain and may also be endogenous in humans. The compound appears to be a peptide, but has yet to be purified and fully characterized.

<span class="mw-page-title-main">3-MeO-PCMo</span> Chemical compound

3-MeO-PCMo is a dissociative anesthetic drug which is similar in structure to phencyclidine and been sold online as a designer drug. The inhibitory effect of 3-MeO-PCMo on the reduction in the density of the drebrin clusters by NMDAR stimulation with glutamic acid is lower than that of PCP or 3-MeO-PCP, with half maximal inhibitory concentration (IC50) values of 26.67 μM (3-MeO-PCMo), 2.02 μM (PCP) and 1.51 μM (3-MeO-PCP).

<span class="mw-page-title-main">3-HO-PCP</span> Chemical compound

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

<span class="mw-page-title-main">4-Keto-PCP</span> Chemical compound

4-Keto-PCP is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It has potency in between that of ketamine and phencyclidine but with somewhat more sedating effects in animal studies.

References

  1. Nabeshima, Toshitaka; Yamaguchi, Kazumasa; Fukaya, Hiroaki; Hiramatsu, Masayuki; Furukawa, Hiroshi; Kameyama, Tsutomu (1985). "Simultaneous determination of phencyclidine and its major metabolites in biological samples by high-performance liquid chromatography". Research Communications in Substances of Abuse. 6 (2): 65–78.
  2. Nakahara, Yuji; Takahashi, Kazunori; Sakamoto, Tomoaki; Tanaka, Akira; Hill, Virginia A.; Baumgartner, Werner A. (1997). "Hair analysis for drugs of abuse XVII. Simultaneous detection of PCP, PCHP, and PCPdiol in human hair for confirmation of PCP use". Journal of Analytical Toxicology. 21 (5): 356–362. doi:10.1093/jat/21.5.356. PMID   9288587.