Conformational equilibria in the 2-amino-1,2-diphenylethanol system. I. Nuclear magnetic resonance studies

Munk, Morton E.; Meilahn, Marcus K.; Franklin, Paul J.

doi:10.1021/jo01273a025

Cited by 22 publications

(7 citation statements)

References 1 publication

(1 reference statement)

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“…Next, relative stereochemistry of the diphenpipenol constitutional isomer was determined to be erythro (Figure 1), based on the observed (small) coupling constant ( 3 J = 3.2 Hz) between the two methine protons (23). A full account supporting this assignment is given in the Supporting information (Supplementary Figure S22).…”

Section: Nmr Analysis and Optical Rotationmentioning

confidence: 99%

Report on a New Opioid NPS: Chemical and In Vitro Functional Characterization of a Structural Isomer of the MT-45 Derivative Diphenpipenol

Cannaert

Hulpia

Risseeuw

et al. 2020

Journal of Analytical Toxicology

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In this paper, the identification and full characterization of a novel non-fentanyl opioid sourced online, which is a member of the 1-substituted-4-(1,2-diphenylethyl)piperazine derivatives related to MT-45, is reported. The sample was sold under the name ‘diphenpipenol’, (3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-phenylethyl]phenol), although extensive NMR analysis showed that the product obtained was actually a diphenpipenol structural isomer, (2-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2-diphenylethanol). Liquid chromatography time-of-flight mass spectrometry (QTOF-MS) identified an exact mass for the protonated molecule of m/z 389.2264, with 2 prominent fragment ions (m/z 91.0567 and 150.0937), which were not reported in earlier literature describing MT-45 derivatives. The chemical characterization was finalized by gas chromatography mass-spectrometry (GC-MS), high-performance liquid chromatography diode array detector (HPLC-DAD) and Fourier-transform infrared spectroscopy (FT-IR) analyses. This product is a clear example of the trend that new non-fentanyl opioids are re-appearing on the recreational drug market to escape the recent changes in (inter)national legislation concerning fentanyl analogues. Although in this particular case the product’s potency and efficacy were relatively low, other new non-fentanyl opioids might possess stronger potencies and therefore pose greater health risks for ignorant users. The fact that the product was sold under the wrong name further demonstrates the well-known problematic issue of a mismatch between the adverted and true identity, confirming the irregularities of the online NPS market.

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Section: Nmr Analysis and Optical Rotationmentioning

confidence: 99%

Report on a New Opioid NPS: Chemical and In Vitro Functional Characterization of a Structural Isomer of the MT-45 Derivative Diphenpipenol

Cannaert

Hulpia

Risseeuw

et al. 2020

Journal of Analytical Toxicology

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“…dConfign of phenyl 2-piperidylmethanols has also been established by Dudas and "Spectra were obtd at indicated temp on a Varían Model DP-60 high-resolution spectrometer at a concn of 10%. 6An average of [6][7][8][9][10] runs; values accurate to an estimated ±0.2 Hz. "OH resonance eliminated by addn of D20.…”

mentioning

confidence: 99%

Antimalarial activity and conformation of erythro- and threo-.alpha.-(2-piperidyl)-3,6-bis(trifluoromethyl)-9-phenanthrenemethanol

Olsen¹

1972

J. Med. Chem.

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“…These values are comparable to the coupling constant values observed for pseudoephedrine and ephedrine. 1,2 The relative configurations of products obtained from reduction of α-oxy substituted ketones were determined by comparison of their proton and 13 C NMR spectra to literature reported values.…”

Section: S2mentioning

confidence: 99%

“…The crude product was purified by column chromatography on silica gel with hexane/ethylacetate (4:1) as eluent (0.877 g, 87 % yield as the syn-diastereomer 2c). 5 2c: 1…”

Section: Reduction Of 2-(benzylmethylamino)-1-phenyl-1-propanone (1c)mentioning

confidence: 99%

Diastereoselectivity in the Reduction of α‐Oxy‐ and α‐Amino‐Substituted Acyclic Ketones by Polymethylhydrosiloxane.

2003

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Diastereoselective syntheses Diastereoselective syntheses O 0031Diastereoselectivity in the Reduction of α-Oxyand α-Amino-Substituted Acyclic Ketones by Polymethylhydrosiloxane. -High syn-selectivity is observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones by PMHS in the presence of catalytic amounts of fluoride ions. No epimerization occurs under these conditions. The reduction of α-monoalkylamino ketone (III) proceeds in anti-selective manner with moderate selectivity. The observed diastereoselectivities are explained based on Felkin-Anh and Cram-chelate models. -(NADKARNI*, D.; HALLISSEY, J.; MOJICA, C.; J. Org. Chem. 68 (2003) 2, 594-596; Process Dev. Lab., Pfizer Global Manuf., Groton, CT 06340, USA; Eng.) -Klein 22-031

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Conformational equilibria in the 2-amino-1,2-diphenylethanol system. I. Nuclear magnetic resonance studies

Cited by 22 publications

References 1 publication

Report on a New Opioid NPS: Chemical and In Vitro Functional Characterization of a Structural Isomer of the MT-45 Derivative Diphenpipenol

Report on a New Opioid NPS: Chemical and In Vitro Functional Characterization of a Structural Isomer of the MT-45 Derivative Diphenpipenol

Antimalarial activity and conformation of erythro- and threo-.alpha.-(2-piperidyl)-3,6-bis(trifluoromethyl)-9-phenanthrenemethanol

Diastereoselectivity in the Reduction of α‐Oxy‐ and α‐Amino‐Substituted Acyclic Ketones by Polymethylhydrosiloxane.

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