ChemInform Abstract: CARBON‐13 NUCLEAR MAGNETIC RESONANCE SPECTRA OF PHENCYCLIDINE ANALOGS

Carroll, F. Ivy; Boldt, Karl G.; Williams, E.E.; Brine, George A.

doi:10.1002/chin.198018050

Cited by 3 publications

(2 citation statements)

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“…6 The predominance of the equatorial piperidine ring was found in DMSO-d 6 solutions of PCP⅐HCl. 6,7 Similarly, this conformation was found in the hydrochloride salt of PCP by X-ray investigation. 6,8 X-ray data have shown the axial position of the chlorophenyl group in S-ketamine-(R,R)-tartarate, 9 which also was proved by 13 C-NMR study of protonated ketamine in CDCl 3 solution.…”

supporting

confidence: 56%

Conformational study on ketamine by circular dichroism and ultraviolet spectroscopy

Zsila

Gergely

Szabó³

1999

Chirality

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supporting

confidence: 56%

Conformational study on ketamine by circular dichroism and ultraviolet spectroscopy

Zsila

Gergely

Szabó³

1999

Chirality

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“…PCP is a semi-rigid molecule containing a cyclohexane ring with attached aromatic and piperidine rings (Scheme 1). Preparation, structural elucidation and structure-activity relationships of this family have been investigated [5,6,7]. To date, only cyclic saturated ketones have been used as starting materials for the synthesis of the phencyclidine family [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Properties of 2-Hydroxy-1-(1-phenyltetralyl)piperidine and Some of its Intermediates as Derivatives of Phencyclidine

Ahmadi

Mahmoudi

2011

Arzneimittelforschung

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Phencyclidine (1-(1-phenylcyclohexyl)piperidine, CAS 956-90-1, PCP) has shown analgesic effects. Some of its derivatives were synthesized and their biological properties were studied. To date, only saturated ketones have been used as starting materials for synthesizing the phencyclidine family. In order to show desirable biological activity, the aromatic and piperidine rings are necessary for these compounds. Using alpha-tetralone as a starting material, 2-hydroxy-1-(-phenyltetralyl)piperidine, an analogue of the phencyclidine family, and some of its intermediates were synthesized. This ketone was reacted with phenyl magnesium bromide and the resultant alcohol was reacted with acetic anhydride to give alkene that was treated with potassium permanganate to give diol. This compound was treated with a suspension of sodium azide and trichloroacetic acid to give the azide compound that was reduced with LiAlH4 to give the primary amine. Cyclization of this compound with 1,5-dibromopentane finally gave a tertiary amine. It is predicted that the title compound 2-hydroxy-1-(1-phenyltetralyl)piperidine exerts a potent analgesic effect on acute and phasic pain.

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Positron labeled analogs of TCP: Synthesis of 1−[4−[18F]fluoromethyl-1−(2-thienyl)cyclohexyl]piperidine

Maëda

Tsukiyama

Fukumura

et al. 1991

International Journal of Radiation Applications and Instrumenta

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ChemInform Abstract: CARBON‐13 NUCLEAR MAGNETIC RESONANCE SPECTRA OF PHENCYCLIDINE ANALOGS

Cited by 3 publications

References 1 publication

Conformational study on ketamine by circular dichroism and ultraviolet spectroscopy

Conformational study on ketamine by circular dichroism and ultraviolet spectroscopy

Synthesis and Biological Properties of 2-Hydroxy-1-(1-phenyltetralyl)piperidine and Some of its Intermediates as Derivatives of Phencyclidine

Positron labeled analogs of TCP: Synthesis of 1−[4−[18F]fluoromethyl-1−(2-thienyl)cyclohexyl]piperidine

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