Hyperpolarization of Pyridyl Fentalogues by Signal Amplification By Reversible Exchange (SABRE)

Thomas B. R. Robertson; Lysbeth H. Antonides; Nicolas Gilbert; Sophie L. Benjamin; Stuart K. Langley; Lindsey J. Munro; Oliver B. Sutcliffe; Ryan E. Mewis

doi:10.1002/open.201900273

Hyperpolarization of Pyridyl Fentalogues by Signal Amplification By Reversible Exchange (SABRE)

Thomas B. R. Robertson, Lysbeth H. Antonides, Nicolas Gilbert, Sophie L. Benjamin, Stuart K. Langley, Lindsey J. Munro, Oliver B. Sutcliffe (Lead / Corresponding author), Ryan E. Mewis (Lead / Corresponding author)

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Abstract

Fentanyl, also known as ‘jackpot’, is a synthetic opiate that is 50–100 times more potent than morphine. Clandestine laboratories produce analogues of fentanyl, known as fentalogues to circumvent legislation regarding its production. Three pyridyl fentalogues were synthesized and then hyperpolarized by signal amplification by reversible exchange (SABRE) to appraise the forensic potential of the technique. A maximum enhancement of -168-fold at 1.4 T was recorded for the ortho pyridyl ¹H nuclei. Studies of the activation parameters for the three fentalogues revealed that the ratio of ligand loss trans to hydride and hydride loss in the complex [Ir(IMes)(L)₃(H)₂]⁺ (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene) ranged from 0.52 to 1.83. The fentalogue possessing the ratio closest to unity produced the largest enhancement subsequent to performing SABRE at earth's magnetic field. It was possible to hyperpolarize a pyridyl fentalogue selectively from a matrix that consisted largely of heroin (97 : 3 heroin:fentalogue) to validate the use of SABRE as a forensic tool.

Original language	English
Pages (from-to)	1375-1382
Number of pages	8
Journal	ChemistryOpen
Volume	8
Issue number	12
Early online date	8 Nov 2019
DOIs	https://doi.org/10.1002/open.201900273
Publication status	Published - Dec 2019

Keywords

exchange dynamics
fentalogues
fentanyl
hyperpolarisation
NMR

ASJC Scopus subject areas

General Chemistry

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10.1002/open.201900273Licence: CC BY-NC-ND

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© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
Final published version, 826 KBLicence: CC BY-NC-ND

Cite this

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title = "Hyperpolarization of Pyridyl Fentalogues by Signal Amplification By Reversible Exchange (SABRE)",

abstract = "Fentanyl, also known as {\textquoteleft}jackpot{\textquoteright}, is a synthetic opiate that is 50–100 times more potent than morphine. Clandestine laboratories produce analogues of fentanyl, known as fentalogues to circumvent legislation regarding its production. Three pyridyl fentalogues were synthesized and then hyperpolarized by signal amplification by reversible exchange (SABRE) to appraise the forensic potential of the technique. A maximum enhancement of -168-fold at 1.4 T was recorded for the ortho pyridyl 1H nuclei. Studies of the activation parameters for the three fentalogues revealed that the ratio of ligand loss trans to hydride and hydride loss in the complex [Ir(IMes)(L)3(H)2]+ (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene) ranged from 0.52 to 1.83. The fentalogue possessing the ratio closest to unity produced the largest enhancement subsequent to performing SABRE at earth's magnetic field. It was possible to hyperpolarize a pyridyl fentalogue selectively from a matrix that consisted largely of heroin (97 : 3 heroin:fentalogue) to validate the use of SABRE as a forensic tool.",

keywords = "exchange dynamics, fentalogues, fentanyl, hyperpolarisation, NMR",

author = "Robertson, {Thomas B. R.} and Antonides, {Lysbeth H.} and Nicolas Gilbert and Benjamin, {Sophie L.} and Langley, {Stuart K.} and Munro, {Lindsey J.} and Sutcliffe, {Oliver B.} and Mewis, {Ryan E.}",

note = "Funding Information: Manchester Metropolitan University. Grant Number: 396154510; Fonds de Recherche du Qu{\'e}bec - Nature et Technologie. Grant Number: 206375",

year = "2019",

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doi = "10.1002/open.201900273",

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AU - Robertson, Thomas B. R.

AU - Antonides, Lysbeth H.

AU - Gilbert, Nicolas

AU - Benjamin, Sophie L.

AU - Langley, Stuart K.

AU - Munro, Lindsey J.

AU - Sutcliffe, Oliver B.

AU - Mewis, Ryan E.

N1 - Funding Information: Manchester Metropolitan University. Grant Number: 396154510; Fonds de Recherche du Québec - Nature et Technologie. Grant Number: 206375

PY - 2019/12

Y1 - 2019/12

N2 - Fentanyl, also known as ‘jackpot’, is a synthetic opiate that is 50–100 times more potent than morphine. Clandestine laboratories produce analogues of fentanyl, known as fentalogues to circumvent legislation regarding its production. Three pyridyl fentalogues were synthesized and then hyperpolarized by signal amplification by reversible exchange (SABRE) to appraise the forensic potential of the technique. A maximum enhancement of -168-fold at 1.4 T was recorded for the ortho pyridyl 1H nuclei. Studies of the activation parameters for the three fentalogues revealed that the ratio of ligand loss trans to hydride and hydride loss in the complex [Ir(IMes)(L)3(H)2]+ (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene) ranged from 0.52 to 1.83. The fentalogue possessing the ratio closest to unity produced the largest enhancement subsequent to performing SABRE at earth's magnetic field. It was possible to hyperpolarize a pyridyl fentalogue selectively from a matrix that consisted largely of heroin (97 : 3 heroin:fentalogue) to validate the use of SABRE as a forensic tool.

AB - Fentanyl, also known as ‘jackpot’, is a synthetic opiate that is 50–100 times more potent than morphine. Clandestine laboratories produce analogues of fentanyl, known as fentalogues to circumvent legislation regarding its production. Three pyridyl fentalogues were synthesized and then hyperpolarized by signal amplification by reversible exchange (SABRE) to appraise the forensic potential of the technique. A maximum enhancement of -168-fold at 1.4 T was recorded for the ortho pyridyl 1H nuclei. Studies of the activation parameters for the three fentalogues revealed that the ratio of ligand loss trans to hydride and hydride loss in the complex [Ir(IMes)(L)3(H)2]+ (IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene) ranged from 0.52 to 1.83. The fentalogue possessing the ratio closest to unity produced the largest enhancement subsequent to performing SABRE at earth's magnetic field. It was possible to hyperpolarize a pyridyl fentalogue selectively from a matrix that consisted largely of heroin (97 : 3 heroin:fentalogue) to validate the use of SABRE as a forensic tool.

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Hyperpolarization of Pyridyl Fentalogues by Signal Amplification By Reversible Exchange (SABRE)

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