Synthesis with Improved Yield and Study on the Analgesic Effect of 2-Methoxyphencyclidine

Ahmadi, Abbas; Mahmoudi, Ali

doi:10.1055/s-0031-1296732

Cited by 5 publications

(8 citation statements)

References 14 publications

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“…Spectroscopicdata(IR, 1 Ha nd 13 CN MR, mass)confirmed the structureo fcompound III.The melting points of the knowncompoundsalsoconfirmtheir identity.The purity of eachcompound waschecked by TLC using ethylacetate-hexane ast he eluent.…”

Section: 32formalin Testsupporting

confidence: 52%

“…Phencyclidine (1-(1-phenylcyclohexyl)piperidine,C AS 77-10-1,P CP, I )i sasemi-rigid molecule containing a cyclohexane ring withattached aromaticand piperidine rings(Scheme 1). PCP and its derivativesaffectt he centraln ervous system and displayanalgesic, stimulant, depressantand hallucinogeniceffects becauseofspecificb inding sitesin the brain [1,2].Itisalsoanon-com-petitiveN-methyl-D-asparate( NMDA)receptorantagonist,hasbeen demonstrated top roducep sychomimetic effects on humansand tobeawidelyabused drug [3].…”

Section: Introductionmentioning

confidence: 99%

“…Inthe recenty ears,forobtaining selective,non-competitiveantagonists att he PCP binding siteo nthe NMDA receptorcomplex,severaln ewPCP derivatives (withchangesin substitution on the molecule) have been synthesized and theirpharmacologicalactivities havebeen tested [1,2,[4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl)(cyclohexyl)] morpholine as a new phencyclidine derivative in rats

Ahmadi

Khalili

Hajikhani

et al. 2011

Arzneimittelforschung

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Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 77-10-1, PCP, I) and many of its analogues have been synthesized and their pharmacological properties studied. In this research, new methyl morpholine derivative of phencyclidine (1-[1-(4-methylphenyl) (cyclohexyl)]morpholine, Methyl-PCM, III) was synthesized and the acute and chronic pain activities were studied using tail immersion and formalin tests on rats and compared to PCP and PCM (1-(1-phenylcyclohexyl)morpholine, CAS 2201-40-3, PCP-morpholine, II). The results Indicated that Methyl-PCM (III, 6 mg/kg, i.p) produces more analgesic effects in tail immersion test (as a model of acute thermal pain) in comparison with the PCP, PCM and control groups. Meanwhile, this analgesic effect was markedly shown 5-15 min after the compound III application. In formalin test analysis, the acute pain (phase I) could not be affected by any drugs, but the chronic formalin pain (phase II) could be diminished by PCM and especially compound III. The chronic analgesic effect of Methyl-PCM was markedly shown in the late phase of chronic pain.

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Section: 32formalin Testsupporting

confidence: 52%

Section: Introductionmentioning

confidence: 99%

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Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl)(cyclohexyl)] morpholine as a new phencyclidine derivative in rats

Ahmadi

Khalili

Hajikhani

et al. 2011

Arzneimittelforschung

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“…That MXE induces its antinociceptive effects at doses lower than those classically reported for ketamine could be due to the presence of the methoxy group, which is likely to increase μ‐opioid receptor affinity, and to that of the N‐ ethylamino group that could increase potency of action. Accordingly, the insertion of the 2‐methoxy group in the structure of phencyclidine increases tail‐flick latency and reduces the time to onset of analgesia, compared with ketamine (Ahmadi and Mahmoudi, ). However, MXE‐induced antinociceptive effects might involve different sites in the brain, including non‐NMDA glutamate receptors, and other (not glutamatergic) neurotransmission systems (Forman, ).…”

Section: Discussionmentioning

confidence: 99%

Methoxetamine affects brain processing involved in emotional response in rats

Zanda

Fadda

Antinori

et al. 2017

British J Pharmacology

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BACKGROUND AND PURPOSEMethoxetamine (MXE) is a novel psychoactive substance that is emerging on the Internet and induces dissociative effects and acute toxicity. Its pharmacological effects have not yet been adequately investigated. EXPERIMENTAL APPROACHWe examined a range of behavioural effects induced by acute administration of MXE (0.5-5 mg·kg À1 ; i.p.) in rats and whether it causes rapid neuroadaptive molecular changes. KEY RESULTS MXE (0.5-5 mg·kgÀ1 ) affected motor activity in a dose-and time-dependent manner, inducing hypermotility and hypomotility at low and high doses respectively. At low and intermediate doses (0.5 and 1 mg·kg À1 ), MXE induced anxious and/or obsessive-compulsive traits (marble burying test), did not significantly increase sociability (social interaction test) or induce spatial anxiety (elevated plus maze test). At a high dose (5 mg·kg À1 ), MXE induced transient analgesia (tail-flick and hot-plate test), decreased social interaction time (social interaction test) and reduced immobility time while increasing swimming activity (forced swim test), suggesting an antidepressant effect. Acute MXE administration did not affect self-grooming behaviour at any dose tested. Immunohistochemical analysis showed that behaviourally active doses of MXE (1 and 5 mg·kg À1 ) increased phosphorylation of ribosomal protein S6 in the medial prefrontal cortex and hippocampus. CONCLUSIONS AND IMPLICATIONSMXE differentially affected motor activity, behaviour and emotional states in rats, depending on the dose tested. As reported for ketamine, phosphorylation of the ribosomal protein S6 was increased in MXE-treated animals, thus providing a 'molecular snapshot' of rapid neuroadaptive molecular changes induced by behaviourally active doses of MXE. Abbreviations

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“…PCP and its derivativesinfluencethe centraln ervous system and consequentlydisplayanalgesic, stimulant, depressantand hallucinogeniceffects,duetospecific binding sitesin the brain [17].Knowing its non-compe-titiveN-methyl-D-asparate(NMDA)receptorantagonist action,P CP hasbeen demonstrated top roducep sychotomimeticeffects in humans,soi tisawidelyabused drug [18,19].…”

Section: Discussionmentioning

confidence: 99%

Synthesis and analgesic effects of new pyrrole derivatives of phencyclidine in mice

Ahmadi

Solati

Hajikhani

et al. 2011

Arzneimittelforschung

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Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 956-90-1, PCP, I) and many of its analogues have shown some pharmacological effects. In this study, new pyrrole derivatives of I (1-(1-phenylcyclohexyl)pyrrole, II and 1-[1-(4-methylphenyl)(cyclohexyl)]pyrrole, III) and their intermediates were synthesized and the acute and chronic pains were examined on mice 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 were compared with the PCP and control groups. The results indicated that III generated higher analgesic effects in the tail immersion test compared to the PCP and control (dimethyl sulfoxide, DMSO) groups, demonstrating a marked and significant increase in tail immersion latency, but this effect was not observed for II in the dose of 1 mg/kg. The formalin test showed that III was effective in acute chemical pain (phase I, 0-5 min after injection), but was not effective for II at the same dosage compared to the PCP and control groups. Also chronic pain will be significantly attenuated by III but II was not effective as compared to the other groups. It is concluded that substitution of the aromatic pyrrole ring instead of piperidine in the PCP molecule will not be effective alone in tail immersion and formalin tests but the addition of a methyl group (with high electron donating and dipole moments) on the phenyl group plus substitution of the aromatic pyrrole ring can be effective in acute and chronic pain compared to the PCP and control groups.

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Synthesis with Improved Yield and Study on the Analgesic Effect of 2-Methoxyphencyclidine

Cited by 5 publications

References 14 publications

Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl)(cyclohexyl)] morpholine as a new phencyclidine derivative in rats

Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl)(cyclohexyl)] morpholine as a new phencyclidine derivative in rats

Methoxetamine affects brain processing involved in emotional response in rats

Synthesis and analgesic effects of new pyrrole derivatives of phencyclidine in mice

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