Towards identifying nicomorphine administration in doping control: synthesis of metabolites

Giuseppe Floresta; Ivana Gavrilovic; Scarlett  Devey; Rhian  Harris; David Cowan; Vincenzo Abbate

doi:10.4155/bio-2021-0076

Towards identifying nicomorphine administration in doping control: synthesis of metabolites

Giuseppe Floresta, Ivana Gavrilovic, Scarlett Devey, Rhian Harris, David Cowan, Vincenzo Abbate

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Abstract

Aim: Nicomorphine is rapidly metabolized mainly to the biologically active 6-nicotinoyl morphine and morphine. In sport, morphine and nicomorphine use is prohibited whereas codeine use is permitted. Accredited laboratories routinely test for morphine hence must be able to distinguish morphine, as a metabolite of a prohibited substance, from that whose use is permitted. Results: Here we show a relatively simple method to synthesize the nicomorphine metabolites, 3-nicotinoyl and 6-nicotinoyl morphine, and indicate how they may be used to identify nicomorphine administration. Conclusion: This approach should help confirm that it is not codeine, an allowable analgesic in sport, that has been administered.

Original language	English
Pages (from-to)	1415-1425
Number of pages	11
Journal	Bioanalysis
Volume	13
Issue number	18
Early online date	16 Sept 2021
DOIs	https://doi.org/10.4155/bio-2021-0076
Publication status	Published - Sept 2021

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Towards identifying nicomorphine administration_FLORESTA_Accepted2September2021_GREEN AAMAccepted author manuscript, 443 KB

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abstract = "Aim: Nicomorphine is rapidly metabolized mainly to the biologically active 6-nicotinoyl morphine and morphine. In sport, morphine and nicomorphine use is prohibited whereas codeine use is permitted. Accredited laboratories routinely test for morphine hence must be able to distinguish morphine, as a metabolite of a prohibited substance, from that whose use is permitted. Results: Here we show a relatively simple method to synthesize the nicomorphine metabolites, 3-nicotinoyl and 6-nicotinoyl morphine, and indicate how they may be used to identify nicomorphine administration. Conclusion: This approach should help confirm that it is not codeine, an allowable analgesic in sport, that has been administered.",

author = "Giuseppe Floresta and Ivana Gavrilovic and Scarlett Devey and Rhian Harris and David Cowan and Vincenzo Abbate",

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AU - Floresta, Giuseppe

AU - Gavrilovic, Ivana

AU - Devey, Scarlett

AU - Harris, Rhian

AU - Cowan, David

AU - Abbate, Vincenzo

PY - 2021/9

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N2 - Aim: Nicomorphine is rapidly metabolized mainly to the biologically active 6-nicotinoyl morphine and morphine. In sport, morphine and nicomorphine use is prohibited whereas codeine use is permitted. Accredited laboratories routinely test for morphine hence must be able to distinguish morphine, as a metabolite of a prohibited substance, from that whose use is permitted. Results: Here we show a relatively simple method to synthesize the nicomorphine metabolites, 3-nicotinoyl and 6-nicotinoyl morphine, and indicate how they may be used to identify nicomorphine administration. Conclusion: This approach should help confirm that it is not codeine, an allowable analgesic in sport, that has been administered.

AB - Aim: Nicomorphine is rapidly metabolized mainly to the biologically active 6-nicotinoyl morphine and morphine. In sport, morphine and nicomorphine use is prohibited whereas codeine use is permitted. Accredited laboratories routinely test for morphine hence must be able to distinguish morphine, as a metabolite of a prohibited substance, from that whose use is permitted. Results: Here we show a relatively simple method to synthesize the nicomorphine metabolites, 3-nicotinoyl and 6-nicotinoyl morphine, and indicate how they may be used to identify nicomorphine administration. Conclusion: This approach should help confirm that it is not codeine, an allowable analgesic in sport, that has been administered.

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Towards identifying nicomorphine administration in doping control: synthesis of metabolites

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