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Reference Materials 2017 Fentanyls Reference materials 2017 LGC Quality ISO 9001 ISO/IEC 17025 ISO Guide 34 GMP/GLP ISO 13485 ISO/IEC 17043 Science for a safer world The emergence of fentanyls as drugs of abuse represents the greatest challenge to forensic toxicology since the appearance of the synthetic cannabinoids. The many fentanyl variants available and the low levels of material present in biological samples mean that investigation of overdose cases now has to be particularly thorough in order to establish whether fentanyls are involved. Ric Treble Scientific Advisor LGC LGC Standards is part With 2,600 professionals working When you make a decision using our in 21 countries, our analytical resources, you can be sure it’s based of LGC – the global measurement and quality control on precise, robust data. And that leader in measurement services are second-to-none. together, we’re creating fairer, safer, standards, reference more confident societies worldwide. As the global leader, we provide the materials, laboratory widest range of reference materials lgcstandards.com services and available from any single supplier. proficiency testing. There is significant evidence The chemical structure of Fentanyl: from a small number of post- mortem results of recent drug user deaths and from police seizures that some heroin may contain fentanyl or carfentanyl added by dealers. These are highly potent synthetic opiods and very small amounts can cause severe or even fatal toxicity. Professor Paul Cosford, Director for Health Protection & Medical Director LGC offers the most The challenge The potency of fentanyls means that The LGC response seizures suspected to contain them extensive and up-to- The illicit use of synthetic opioids, and should be handled with caution, In response to the increasing date range of fentanyls particularly fentanyls, has become and personal protective equipment problem of fentanyls and ‘designer’ reference materials. an increasing cause for concern, is advisable to prevent accidental versions, a range of reference particularly in North America and ingestion or contamination. It also materials have been produced for Europe. These materials produce their means that there are usually only very these materials, their precursors and effects via the mu-opioid receptors low levels of material to be found in their major metabolites. which respond to morphine, but biological samples, so that they may fentanyls have a significantly greater be overlooked, particularly if other LGC Standards provides the widest potency, so that overdose and death ‘traditional’ opiates are present. range of reference materials by respiratory arrest is a serious risk. The US Centre for Disease Control available from any single supplier. Where fentanyls have entered the (CDC) has issued a Health Advisory We work closely with leading opioid misuse market, deaths by notice advising that, where there is manufacturers to provide improved overdose have increased significantly. a local increase in opiate overdoses, access to reference materials, or if fentanyls have been identified in with an increasingly large range Although encountered as diverted local drug seizures, fentanyls should of parameters, for laboratories pharmaceuticals, fentanyls are also be looked for in toxicology testing. worldwide. LGC Standards has both being illicitly synthesised. As well as Similarly, the European Monitoring extensive reference material sales As legislation has been being sold as heroin replacements or Centre for Drugs and Drug Addiction experience and technical expertise deployed to control named ‘boosters’, fentanyls have increasingly (EMCDDA) has warned of a risk of that allows us to work in successful fentanyls, a range of ‘designer’ been seen in the form of counterfeit under-reporting of fentanyls and called partnership with our customers. pharmaceuticals, usually intended for enhanced forensic identification. versions have been produced to have the appearance of tablets to circumvent control. containing oxycodone or hydrocodone, such as Vicodin or Oxycontin. In North America, where a significant population of abusers of prescription opioids already existed, circulation and use of fentanyl-containing tablets have become widespread, with many deaths resulting, to the extent that a ‘health emergency’ has recently been declared in British Columbia (Canada). LGC has expert toxicologists who constantly monitor the market to identify new fentanyl substances on the market. Currently available reference standards for fentanyls include: Ref no: Fentanyls Ref no: Fentanyls Ref no: Fentanyls 1.0 Precursors and impurities 5.0 Alfentanils 17.0 Ohmefentanyls 1.1 4-Anilopiperadine 5.1 Alfetanil 17.1 Ohmefentanyl 1.2 4-Anilino-1-benzylpiperidine 5.2 Alfetanil-D3 17.2 Ohmefentanyl-D3 1.3 N-Phenethyl-4-piperidone (NPP) 1.4 Despropionylfentanyl (4-ANPP) 6.0 Benzodioxole fentanyls 18.0 Remifentanils 1.5 Despropionylfentanyl-D5 6.1 Benzodioxole fentanyl 18.1 Remifentanil 1.6 Despropionyl-ortho-fluorofentanyl 18.2 Remifentanil-13C6 1.7 Despropionyl-para-fluorofentany 7.0 Benzyl fentanyls 7.1 Benzyl fentanyl 19.0 Sufentanils 2.0 Fentanyls 7.2 Benzyl fentanyl-D3 19.1 Sufentanil 2.1 Fentanyl 19.2 Sufentanil-D3 2.2 Fentanyl-D5 8.0 Butyryl fentanyls 19.3 Sufentanil-D5 2.3 para-Chlorofentanyl 8.1 Butyryl fentanyl 2.4 ortho-Fluorofentanyl 8.2 Butyryl fentanyl-D5 20.0 Thienyl fentanyls 20.1 Thienyl fentanyl 2.5 meta-Fluorofentanyl 8.3 α-Methyl-butyryl fentanyl 20.2 Thienyl fentanyl-D3 2.6 para-Fluorofentanyl 8.4 cis-3-Methyl-butyryl fentanyl 2.7 para-Fluorofentanyl-D3 8.5 4-MeO-butyryl fentanyl 8.6 4-MeO-butyryl fentanyl-D7 21.0 Tertahydrofuran fentanyls 2.8 para-Fluorofentanyl-D5 21.1 Tertahydrofuran fentanyl 2.9 beta-Hydroxyfentanyl 8.7 ortho-Fluorobutyrylfentanyl 2.10 beta-Hydroxyfentanyl-D3 8.8 meta-Fluorobutyrylfentanyl 22.0 Thiofentanyls 2.11 omega-Hydroxyfentanyl 8.9 para-Fluorobutyrylfentanyl 22.1 Thiofentanyl 2.12 omega-Hydroxyfentanyl-D5 8.10 para-Fluorobutyrylfentanyl-D7 22.2 Thiofentanyl-D3 2.13 omega-1-Hydroxyfentanyl 22.3 beta-Hydroxythiofentanyl 2.14 omega-1-Hydroxyfentanyl-D5 9.0 Isobutyryl fentanyls 22.4 beta-Hydroxythiofentanyl-D3 9.1 Isobutyryl fentanyl 2.15 2-Hydroxyfentanyl 22.5 beta-Hydroxythiofentanyl-D5 9.2 Isobutyryl fentanyl-D5 2.16 2-Hydroxyfentanyl-D5 22.6 alpha-Methylthiofentanyl 9.3 para-Chloroisobutyrylfentanyl 2.17 para-Methoxyfentanyl 22.7 3-Methylthiofentanyl 9.4 para-Fluoroisobutyrylfentanyl 2.18 alpha-Methylfentanyl 22.8 3-Methylthiofentanyl-D3 2.19 alpha-Methylfentanyl-D3 10.0 Carfentanyls 2.20 beta-Methylfentanyl 10.1 Carfentanil 23.0 Valerylfentanyls 23.1 Valerylfentanyl 2.21 para-Methylfentanyl 10.2 Carfentanil-D5 23.2 Valerylfentanyl-D5 2.22 3-Methylfentanyl 10.3 N-Me carfentanil 2.23 cis-3-Methylfentanyl 10.4 Benzyl carfentanil 2.24 cis-3-Methylfentanyl-D3 24.0 Norfentanyl metabolites 24.1 Acetyl norfentanyl 2.25 trans-3-Methylfentanyl 11.0 Cyclopentyl fentanyls 24.2 Acetyl norfentanyl-D5 2.26 2-Oxofentanyl 11.1 Cyclopentyl fentanyl 42.3 Acetyl norfentanyl-13C6 2.27 2-Oxofentanyl-D5 12.0 Furanyl fentanyls 42.4 Butyryl norfentanyl 3.0 Acetyl fentanyls 12.1 Furanyl fentanyl 24.5 Furanyl norfentanyl 3.1 Acetyl fentanyl 12.2 Furanyl fentanyl-D5 24.6 omega-1-Hydroxynorfentanyl 3.2 Acetyl fentanyl-D5 12.3 3-Furanyl fentanyl (3-furan positional 24.7 omega-1-Hydroxynorfentanyl-D5 3.3 Acetyl fentanyl -13C6 isomer) 24.8 Norcarfentanil 3.4 Acetyl fentanyl, 4-Me (on phenylethyl) 24.9 Norfentanyl analogue 13.0 Furanylethylfentanyls (Furanylethyl 24.10 Norfentanyl-D3 3.5 Acetyl fentanyl, 4-Me (on phenylethyl) replaces phenethyl) 24.11 Norfentanyl-D5 analogue-D5 13.1 Furanylethylfentanyl 24.12 Norlofentanil 3.6 alpha-Methylacetylfentanyl 24.13 Norlofentanil-D3 3.7 alpha-Methylacetylfentanyl-D3 14.0 Lofentanils 24.14 Normethylfentanyl 14.1 Lofentanil 24.15 Normethylfentanyl-D3 4.0 Acrylfentanyls 14.2 Lofentanil-D3 24.16 Norsulfentanil 4.1 Acrylfentanyl 24.17 Norsulfentanil-D3 4.2 para-Fluoro acrylfentanyl 15.0 Methoxyacetylfentanyls 15.1 Methoxyacetylfentanyl 25.0 Other metabolites 25.1 Butyryl fentanyl carboxy metabolite 16.0 Ocfentanils 16.1 Ocfentanil 16.2 Ocfentanil-D5 Visit our webshop at: lgcstandards.com 11 14 7 18 10 12 5 4 6 13 19 8 2 16 17 3 9 1 15 For full listing of offices see lgcstandards.com 1 Brazil 6 Hungary 11 Nordic countries 16 Spain Tel: +55 12 3302 5880 Tel: +49 (0)281 9887 0 Tel: +49 (0)281 9887 0 Tel: +34 (0)93 308 4181 Email: [email protected] Email: 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