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Reference materials 2017

Fentanyls

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 TrebleScientific AdvisorLGC

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The chemical structure of Fentanyl:There is significant evidence 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

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The challenge

The illicit use of synthetic opioids, and particularly fentanyls, has become an increasing cause for concern, particularly in North America and Europe. These materials produce their effects via the mu-opioid receptors which respond to morphine, but fentanyls have a significantly greater potency, so that overdose and death by respiratory arrest is a serious risk. Where fentanyls have entered the opioid misuse market, deaths by overdose have increased significantly.

Although encountered as diverted pharmaceuticals, fentanyls are also being illicitly synthesised. As well as being sold as heroin replacements or ‘boosters’, fentanyls have increasingly been seen in the form of counterfeit pharmaceuticals, usually intended to have the appearance of tablets 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).

The potency of fentanyls means that seizures suspected to contain them should be handled with caution, and personal protective equipment is advisable to prevent accidental ingestion or contamination. It also means that there are usually only very low levels of material to be found in biological samples, so that they may be overlooked, particularly if other ‘traditional’ opiates are present. The US Centre for Disease Control (CDC) has issued a Health Advisory notice advising that, where there is a local increase in opiate overdoses, or if fentanyls have been identified in local drug seizures, fentanyls should be looked for in toxicology testing. Similarly, the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) has warned of a risk of under-reporting of fentanyls and called for enhanced forensic identification.

The LGC response

In response to the increasing problem of fentanyls and ‘designer’ versions, a range of reference materials have been produced for these materials, their precursors and their major metabolites.

LGC Standards provides the widest range of reference materials available from any single supplier. We work closely with leading manufacturers to provide improved access to reference materials, with an increasingly large range of parameters, for laboratories worldwide. LGC Standards has both extensive reference material sales experience and technical expertise that allows us to work in successful partnership with our customers.

LGC offers the most extensive and up-to-date range of fentanyls reference materials.

As legislation has been deployed to control named fentanyls, a range of ‘designer’ versions have been produced to circumvent control.

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

1.01.11.21.31.41.51.61.7

Precursors and impurities4-Anilopiperadine4-Anilino-1-benzylpiperidineN-Phenethyl-4-piperidone (NPP)Despropionylfentanyl (4-ANPP) Despropionylfentanyl-D5Despropionyl-ortho-fluorofentanylDespropionyl-para-fluorofentany

2.02.12.22.32.42.52.62.72.82.92.102.112.122.132.142.152.162.172.182.192.202.212.222.232.242.252.262.27

Fentanyls Fentanyl Fentanyl-D5para-Chlorofentanylortho-Fluorofentanylmeta-Fluorofentanylpara-Fluorofentanyl para-Fluorofentanyl-D3 para-Fluorofentanyl-D5beta-Hydroxyfentanyl beta-Hydroxyfentanyl-D3omega-Hydroxyfentanyl omega-Hydroxyfentanyl-D5omega-1-Hydroxyfentanyl omega-1-Hydroxyfentanyl-D52-Hydroxyfentanyl 2-Hydroxyfentanyl-D5para-Methoxyfentanylalpha-Methylfentanyl alpha-Methylfentanyl-D3beta-Methylfentanylpara-Methylfentanyl3-Methylfentanylcis-3-Methylfentanyl cis-3-Methylfentanyl-D3trans-3-Methylfentanyl2-Oxofentanyl 2-Oxofentanyl-D5

3.03.13.23.33.4

3.5

3.63.7

Acetyl fentanylsAcetyl fentanyl Acetyl fentanyl-D5 Acetyl fentanyl -13C6Acetyl fentanyl, 4-Me (on phenylethyl) analogue Acetyl fentanyl, 4-Me (on phenylethyl) analogue-D5alpha-Methylacetylfentanyl alpha-Methylacetylfentanyl-D3

4.04.14.2

AcrylfentanylsAcrylfentanylpara-Fluoro acrylfentanyl

Ref no: Fentanyls

5.05.15.2

AlfentanilsAlfetanil Alfetanil-D3

6.06.1

Benzodioxole fentanylsBenzodioxole fentanyl

7.07.17.2

Benzyl fentanylsBenzyl fentanyl Benzyl fentanyl-D3

8.08.18.28.38.48.58.68.78.88.98.10

Butyryl fentanylsButyryl fentanyl Butyryl fentanyl-D5α-Methyl-butyryl fentanylcis-3-Methyl-butyryl fentanyl4-MeO-butyryl fentanyl 4-MeO-butyryl fentanyl-D7ortho-Fluorobutyrylfentanylmeta-Fluorobutyrylfentanylpara-Fluorobutyrylfentanyl para-Fluorobutyrylfentanyl-D7

9.09.19.29.39.4

Isobutyryl fentanylsIsobutyryl fentanyl Isobutyryl fentanyl-D5para-Chloroisobutyrylfentanylpara-Fluoroisobutyrylfentanyl

10.010.110.210.310.4

CarfentanylsCarfentanil Carfentanil-D5N-Me carfentanilBenzyl carfentanil

11.011.1

Cyclopentyl fentanylsCyclopentyl fentanyl

12.012.112.212.3

Furanyl fentanylsFuranyl fentanyl Furanyl fentanyl-D53-Furanyl fentanyl (3-furan positional isomer)

13.0

13.1

Furanylethylfentanyls (Furanylethyl replaces phenethyl)Furanylethylfentanyl

14.014.114.2

LofentanilsLofentanil Lofentanil-D3

15.015.1

MethoxyacetylfentanylsMethoxyacetylfentanyl

16.016.116.2

OcfentanilsOcfentanil Ocfentanil-D5

Ref no: Fentanyls

17.017.117.2

OhmefentanylsOhmefentanyl Ohmefentanyl-D3

18.018.118.2

RemifentanilsRemifentanil Remifentanil-13C6

19.019.119.219.3

SufentanilsSufentanil Sufentanil-D3 Sufentanil-D5

20.020.120.2

Thienyl fentanylsThienyl fentanyl Thienyl fentanyl-D3

21.021.1

Tertahydrofuran fentanylsTertahydrofuran fentanyl

22.022.122.222.322.422.522.622.722.8

ThiofentanylsThiofentanyl Thiofentanyl-D3beta-Hydroxythiofentanyl beta-Hydroxythiofentanyl-D3 beta-Hydroxythiofentanyl-D5alpha-Methylthiofentanyl3-Methylthiofentanyl 3-Methylthiofentanyl-D3

23.023.123.2

ValerylfentanylsValerylfentanyl Valerylfentanyl-D5

24.024.124.242.342.424.524.624.724.824.924.1024.1124.1224.1324.1424.1524.1624.17

Norfentanyl metabolitesAcetyl norfentanyl Acetyl norfentanyl-D5 Acetyl norfentanyl-13C6Butyryl norfentanylFuranyl norfentanylomega-1-Hydroxynorfentanyl omega-1-Hydroxynorfentanyl-D5NorcarfentanilNorfentanyl Norfentanyl-D3 Norfentanyl-D5Norlofentanil Norlofentanil-D3Normethylfentanyl Normethylfentanyl-D3Norsulfentanil Norsulfentanil-D3

25.025.1

Other metabolitesButyryl fentanyl carboxy metabolite

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Fentanyls · PDF fileavailable from any single supplier. ... available from any single supplier. We work closely with leading ... Tel: +359 (0)2 971 4955 Email: [email protected]