Forensic Science International 266 (2016) 469–473

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Forensic Science International

journal homepage: www.elsevier.com/locate/forsciint

Ocfentanil overdose fatality in the recreational drug scene

Vera Coopman a, Jan Cordonnier a,*, Marc De Leeuw b,c, Vincent Cirimele d
a
Eurofins Forensics Belgium, Lieven Bauwensstraat 6, 8200 Brugge, Belgium
b
Emergency Department, Algemeen Stedelijk Ziekenhuis, Merestraat 80, 9300 Aalst, Belgium
c
Department of Forensic Medicine, Ghent University, Campus UZ , De Pintelaan 185, 9000 Gent, Belgium
d
ChemTox, Rue Grüninger 3, 67405 Illkirch, France

A R T I C L E I N F O A B S T R A C T

Article history: This paper describes the first reported death involving ocfentanil, a potent synthetic opioid and structure
Received 17 May 2016 analogue of fentanyl abused as a new psychoactive substance in the recreational drug scene. A 17-year-
Received in revised form 4 July 2016 old man with a history of illegal substance abuse was found dead in his home after snorting a brown
Accepted 5 July 2016
powder purchased over the internet with bitcoins. Acetaminophen, caffeine and ocfentanil were
Available online 17 July 2016
identified in the powder by gas chromatography mass spectrometry and reversed-phase liquid
chromatography with diode array detector.
Keywords:
Quantitation of ocfentanil in biological samples was performed using a target analysis based on
Ocfentanil
liquid–liquid extraction and ultra performance liquid chromatography tandem mass spectrometry. In
Fentanyl analogue
Tissue distribution the femoral blood taken at the external body examination, the following concentrations were measured:
New psychoactive substances (NPS) ocfentanil 15.3 mg/L, acetaminophen 45 mg/L and caffeine 0.23 mg/L. Tissues sampled at autopsy were
Ultra performance liquid chromatography analyzed to study the distribution of ocfentanil. The comprehensive systematic toxicological analysis on
mass spectrometry (UPLC-MS) the post-mortem blood and tissue samples was negative for other compounds.
Based on circumstantial evidence, autopsy findings and the results of the toxicological analysis, the
medical examiner concluded that the cause of death was an acute intoxication with ocfentanil. The
manner of death was assumed to be accidental after snorting the powder.
ß 2016 Elsevier Ireland Ltd. All rights reserved.

1. Introduction tissues was performed using liquid–liquid extraction and ultra

Ocfentanil is a synthetic opioid and structure analogue of
fentanyl. Ocfentanil (also called A-3217) was developed in
the early 1990s in the attempt to obtain an analgesic opioid with
less cardiovascular and respiratory effects. The activity of
ocfentanil was studied in human volunteers, showing that
ocfentanil is similar in action to fentanyl, given effective
analgesia at 1 mg/kg and being approximately 2 times as potent
as fentanyl. Nausea, itching and dose-dependent potentially life-
threatening respiratory depression are reported side effects of
fentanyl and analogues [1–5]. Ocfentanil is not approved for
medical use.
To the author’s knowledge, this paper describes the first
reported death involving ocfentanil abused as a new psychoactive
substance (NPS). The intoxication occurred in March 2015 in
Belgium [6,7]. A target analysis on ocfentanil in the postmortem
* Corresponding author. Tel.: +32 50 31 02 52; fax: +32 50 31 02 54.
E-mail address: jancordonnier@eurofins.be (J. Cordonnier).
performance liquid chromatography tandem mass spectrometry
operating in multiple reaction monitoring mode.
2. Case history
A 17-year-old man was found dead in his home, seated and
leaning forward on the toilet at 6:00 am. The victim was last seen
alive at 22:30 pm when his parents went to sleep. No farewell
letter was present. The parents stated that their son has left school
at age 15 and never left the house. He stopped taken antidepres-
sants 3 month before and was prescribed sleeping medication. The
young man had a history of illegal substance abuse and was
previously hospitalized with an acute intoxication due to the
combined intake of cocaine and sleeping tablets. The abused
products were purchased over the internet with bitcoins. Drug
paraphernalia were found in the proximity of the victim: a brown
powder (2.07 g) in a small zip-locked plastic bag which was lying
on a card with a straw. Residue of a brown powder, similar to the
powder in the bag, were present on the card.

http://dx.doi.org/10.1016/j.forsciint.2016.07.005
0379-0738/ß 2016 Elsevier Ireland Ltd. All rights reserved.
470 V. Coopman et al. / Forensic Science International 266 (2016) 469–473
3. Materials and methods
3.1. Materials
Certified reference ocfentanil (N-(2-fluorophenyl)-2-methoxy-
N-[1-(2-phenylethyl)-4-piperidyl]acetamide) was obtained from
Viwit Pharmaceutical co., Ltd (Shanghai, China). The reference
material fentanyl-d5 100 mg/mL in methanol was from Cerilliant
(Round Rock, Texas). Standard compounds were diluted in
methanol (1 mg/mL) and stored at 18 8C. Methanol and acetoni-
trile were obtained from Fisher Chemical (Fisher Bioblock,
Belgium). Formic acid 98–100% was purchased from Merck
(VWR, Leuven, Belgium). Water was purified by a Milli-Q system
obtained from Millipore. All solvents and inorganic chemicals were
of analytical grade. The potassium carbonate solution was
prepared by dissolving 13.6 g of anhydrous K2CO3 (VWR, Leuven,
Belgium) into a 100 mL volumetric flask and made up to volume
with water.
3.2. Instrumentation
The UPLC-MS/MS analysis was performed using a Acquity
separations module coupled to the Acquity TQD mass detector
equipped with ES interface (Waters Milford, MA, USA). Chro-
matographic separation was achieved using a Acquity UPLC HSS
C18 column (150 mm length x 2.1 mm i.d., 1.8 mm particle size)
with a HSS C18 Vanguard column (5 mm length x 2.1 mm i.d.,
1.8 mm particle size) as guard column at 50 8C. The mobile phases
consisted of 0.15% formic acid (A) and 0.15% formic acid in
acetonitrile (B). The following gradient elution was used (runtime
15.00 min), starting with 13% B held for 0.50 min., increased to 50%
B in 9.50 min., changed to 95% B in 0.75 min and held for 1.50 min.,
and finally changed back to initial conditions in 0.25 min and held
for 2.50 min. The flow rate was 0.400 mL/min. The electrospray
source was operated in the positive ionisation mode (ES+). Product
ions were obtained by collision-induced dissociation which
allowed the MS/MS to be operated in the multiple reaction
monitoring (MRM) mode. The MRM transitions and conditions for
the measurement of ocfentanil (retentiontime: 5.24 min.); 371.00/
188.00 (qualifier) and 371.00/105.00; cone voltage 28 V; collision
energy 24 V and 32 V, respectively; fentanyl-d5 (retentiontime:
6.26 min.): 342.45/188.25 (qualifier) and 342.45/105.10; cone
voltage 40 V; collision energy 25 V and 38 V, respectively. Quantita-
tions were carried out using the first transition (qualifier). For
confirmation, the percent ratio of the second transition to the
qualifier was calculated and monitored. The source temperature and
desolvation gas (nitrogen) temperature were set at 150 8C and 400 8C,
respectively. The gas flow was delivered at a rate of 800 L/h. The
capillary voltage was 3.00 kV. Waters Mass-lynx system software
Version 4.1 was used for instrument control and quantitation.
3.3. Samples
The brown powder in the small zip-locked plastic bag was
submitted to the laboratory for analysis. Femoral blood, vitreous
humor and a swab of the mucous membrane of the nose were
taken at the external body examination by the medical examiner at
11:00 am. The blood samples contained respectively sodium
fluoride and EDTA as preservative.
An autopsy was carried out 3 days later. Multiple samples were
taken for toxicological investigation: cardial blood (without
preservative and EDTA, respectively), urine, stomach content
(40 mL), liver, kidney, brain tissue, bile and a hair sample from the
scalp. The tissue samples were stored at 18 8C for 6 weeks until
arrival of the reference compound ocfentanil and before the
distribution study was performed.
4. Methods
4.1. Systematic toxicological analysis
The brown powder was subjected to the authors systematic
toxicology identification scheme (ISO/IEC 17025:2005 accredited)
based on analysis of freshly prepared methanolic sample solution
on reversed-phase liquid chromatography with diode array
detector (HPLC/PDA) and gas chromatography mass spectrometry
(GC/MS) as previously described [8].
A comprehensive systematic toxicological analysis was per-
formed on the post-mortem tissue samples to investigate for illegal
drugs, medical drugs, alcohol, volatile substances and other
poisons. Blood was analyzed for the presence of carboxyhemoglo-
bin and cyanide. Screening for the presence of basic drugs in urine
and stomach contents was performed by GC/MS and in blood by
HPLC/PDA. Analysis for the presence of alcohol in blood, vitreous
humor and urine and of other volatile substances in blood was
performed by gas chromatography and static headspace gas
chromatography with flame ionisation detector. The screening for
the presence of illicit drugs of abuse and medical drugs (including
opiates, amphetamines, methadone and metabolite, cocaine and
metabolites, ketamine/norketamine, fentanyl/norfentanyl and
medical analogues, cannabinoids, benzodiazepines, narcotic
analgesics, antidepressant drugs and several new psychoactive
substances) were investigated in blood and b-glucuronidase
hydrolyzed urine using UPLC-MS/MS methods. Color spot tests
on urine and gastric content were used to detect salicylates,
acetaminophen, phenothiazines and imipramines.
Quantitative determination of acetaminophen (matrix-
matched standard calibration using acetaminophen-d4 as
internal standard) and caffeine (matrix-matched external
standard calibration) in the blood taken at the external body
examination (with EDTA as preservative) were performed using
UPLC-MS/MS using the same liquid/liquid extraction and LC-
conditions as applied for ocfentanil. The hair was analyzed on the
presence for amphetamine, methamphetamine, MDMA, MDA,
MDEA, cocaine, benzoylecgonine, norcocaine, cocaethylene,
morphine, 6-monoacetylmorphine, codeine, tetrahydrocannabinol,
cannabidiol, cannabinol, ketamine and norketamine. Hair specimen
was decontaminated twice with methylene chloride. The proximal
6 cm-long hair section was homogenized by cutting with scissors
into small pieces (< 1 mm). Twenty mg of hair were incubated
overnight at 40 8C using 400 mL of methanol in the presence of the
deuterated analogues as internal standard. An aliquot of the media
was evaporated to dryness and injected into the UPLC-MS/MS in
MRM mode (ES+). Each compound was identified based on two MRM
transitions and quantified using a calibration curve (ISO/IEC
17025:2005 accredited).
4.2. Sample preparation and extraction
The biological tissue samples were submitted to toxicological
examination. Liquid–liquid extraction was made after homogeni-
zation. Kidney, liver, stomach content (semi-solid), bile and brain
tissue were homogenized in water at a ratio (m/m) of 1:2 or 1:5 by
means of a Ultra Turrax1 (IKA T18 basis). The swab of the mucous
membrane of the nose was extracted in 0.5 mL ultrapure water.
To a 0.5 mL aliquot of sample (blood, urine, vitreous humor, bile,
extract of nose swab) or 0.5 g homogenized tissue sample, 5 mL of
internal standard solution (fentanyl-d5 1 mg/mL) was added. After
addition of the internal standard solution (5 ng fentanyl-d5/
sample), the samples were vortex mixed and allowed to equilibrate
30 min. prior to extraction. Alkalinization was obtained by
addition of 1.0 mL potassium carbonate solution followed by
agitation in a vortex mixer. Extraction was performed with 5 mL of
 V. Coopman et al. / Forensic Science International 266 (2016) 469–473 471

a mixture of n-hexane: ethyl acetate (7:3, v/v). After vortex mixing 5. Results
during 2 min. and centrifugation at 3000 rpm for 5 min, the upper
organic layer was evaporated to dryness under a slow stream of The initial analysis of the powder by HPLC/PDA revealed the
nitrogen at 40 8C. The dried extracts were reconstituted in 0.5 mL presence of caffeine, acetaminophen, benzoic acid and an
of initial mobile phase. The reconstituted tissue extracts were unknown. In addition to these identified compounds, a hit for
centrifuged at 14000 rpm for 5 min. A 10 mL aliquot was injected ocfentanil was found on GC/MS by means of computer based
into the UPLC-MS/MS system. A blank was injected before every library search of the SWGDRUG Mass Spectral Library (Version 2.2)
sample. All samples were analysed in duplicate or triplicate and installed on the Agilent Chemstation. After arrival of the reference
mean values determined. compound ocfentanil, identification was confirmed based on
retention time and similarity index or mass spectrum. The mass
4.3. Calibration and validation spectrum of the analysis of the brown powder and reference mass
spectrum of ocfentanil and the UV-spectrum of ocfentanil is shown
Calibrators and quality controls (low: 4.2 mg/L; medium: in Figs. 1 and 2, respectively. Quantitative results were obtained by
10.5 mg/L; high: 16.8 mg/L) were prepared by addition of standard analysis of different dilutions of 2 methanolic sample solutions on
solutions to ocfentanil free pooled whole blood prior to extraction. HPLC/PDA using a 5 point calibration curve: acetaminophen 58.4%
Six point calibration curves were constructed within the concen- (m/m), caffeine 13.7% (m/m) and ocfentanil 2.54% (m/m).
tration range 2.1–21.0 mg/L blood (see Table 1.). Calibrators and The comprehensive systematic toxicological analysis of the
controls were different preparations of the same drug standard lot. biological samples, only showed the presence acetaminophen and
Method validation was based on the document ‘Standard Practices caffeine in blood, urine and stomach contents. The following
of Method Validation in Forensic Toxicology’ published by the concentrations were measured in the femoral blood taken at the
Scientific Working Group of Forensic Toxicology [9]. The following external body examination: a high therapeutic concentration of
validation parameters were assessed: calibration model, bias, 45 mg/L acetaminophen and a toxicological irrelevant level of
precision, carry-over, interferences, ionization suppression/en- 0.23 mg/L caffeine. In the 0–6 cm segment of the hair were
hancement, limit of detection (LOD) and limit of quantitation detected: cocaine (0.33 ng/mg), norcocaine (present at a concen-
(LOQ). tration below the LOQ of 0.005 ng/mg), benzoylecgonine (0.14 ng/
The extraction recovery (%) was determined by comparing the mg), 6-monoacetylmorphine (0.54 ng/mg), morphine (1.10 ng/mg)
peak areas of an extracted aqueous quality control (medium) with and codeine (0.11 ng/mg).
the peak areas of an unextracted solution with the same Quantitation of ocfentanil in the biological samples was
concentration (n = 6). The internal standard fentanyl-d5 was added performed using a target analysis based on liquid–liquid extraction
after extraction and before reconstitution of the evaporated and ultra performance liquid chromatography tandem mass
(extracted) quality control. spectrometry. An overview of the assessed validation parameters
and validation data is shown in Table 1. The distribution of
ocfentanil in the post-mortem blood and tissue samples is shown
in Table 2.
Table 1
Validation parameters and validation data. 6. Discussion
Validation parameter Validation data
Ocfentanil is a synthetic opioid and structure analogue of
Calibration model Unweighted linear curve fit, fentanyl-d5 as
fentanyl. The chemical structures of fentanyl (N-(1-phenethyl-4-
internal standard
Mean correlation coefficient (r): 0.9993 piperidyl)-N-phenylpropanamide) and ocfentanil (N-(2-fluoro-
Residual plots were evaluated, confirming that phenyl)-2-methoxy-N-[1-(2-phenylethyl)-4-piperidyl]acetamide)
the used calibration model was appropriate are shown in Fig. 3. In accordance with findings described in opioid
Six point calibration curves with calibration intoxications, pulmonary oedema and lung injury were observed at
levels: 2.1 mg/L, 5.2 mg/L, 10.4 mg/L, 15.7 mg/L
autopsy. The comprehensive systematic toxicological analysis only
and 20.9 mg/L
Bias Measured using three separate samples per revealed the presence of acetaminophen and caffeine. The
concentration over five different runs: recognition and analysis of highly potent, new psychoactive
At concentration low (4.2 mg/L): 0.70% substances in tissues are challenging in postmortem toxicology.
At concentration medium (10.5 mg/L): 1.69%
Without the identification of ocfentanil in the powder and target
At concentration high (16.8 mg/L): 0.10%
Precision Measured using three separate samples per
analysis of postmortem samples with hyphenated techniques, the
concentration over five different runs: presence of ocfentanil would be overlooked due to the low toxic
Within-run CV: 2.86% (low), 1.14% (medium), tissue concentrations. Based on the result of the nose swab and the
1.79% (high) paraphernalia found in the vicinity of the victim, it was concluded
Between-run CV: 3.78% (low), 2.24% (medium),
that the brown powder was snorted.
2.08% (high)
Carryover No carryover was observed after highest Ocfentanil is a very potent opioid (approximately 90 times as
calibrator (n = 5) potent as morphine), making the abuse in the recreational drug
A blanc was run before every sample scene exceptionally dangerous, in particular in opioid intolerant
Interference studies No interfering signal from matrix, internal
users. The decedent had no known history of heroin usage. No
standard, common drugs abuse (including
medical fentanyl analogues) and prescription
punction marks were observed at autopsy. It was not clear what he
medications intended to purchased on the internet. The hair was analyzed on
Ionization suppression/ Post-extraction addition approach on 10 the presence for amphetamine, methamphetamine, MDMA, MDA,
enhancement different postmortem whole blood sources MDEA, cocaine, benzoylecgonine, norcocaine, cocaethylene, mor-
+7.4% (14.6% CV) at concentration low
phine, 6-monoacetylmorphine, codeine, tetrahydrocannabinol,
+6.2% (7.3% CV) at concentration high
Limit of detection LOD and LOQ defined as the value of lowest cannabidiol, cannabinol, ketamine and norketamine to provide
(LOD)/limit of non-zero calibrator (2.1 mg/L) an understanding of the historical pattern of drug use. Cocaine was
quantitation (LOQ) detected in the 0–6 cm hair section at 0.33 ng/mg within two
Recovery 87.6% (4.6% CV)
cocaine metabolites, benzoylecgonine and norcocaine. Cocaine
472 V. Coopman et al. / Forensic Science International 266 (2016) 469–473

Fig. 1. Mass spectrum of the analysis of the brown powder (upper) and reference mass spectrum of ocfentanil present in the SWGDRUG library (lower).

heroin. This is a common component and it is broken down within

Fig. 2. UV-spectrum of ocfentanil (reference solution 50 mg/mL).
concentration is low when compared to the general population of
drug addicts, suggesting that the donor of the hair specimen was
occasionaly exposed to cocaine. Once in the body, heroin
(diamorphine) is broken down in the body to yield 6-mono-
acetylmorphine and morphine. The hair sample was positive for
6-monoacetylmorphine in the 0–6 cm head hair section at a low
concentration (0.54 ng/mg) in view of what can be observed in
recreational drug abusers, suggesting that the submitted hair
belongs to a subject that was occasionaly exposed to heroin over
the last 6 months period before death. The presence of codeine is
likely to be the result of the presence of acetylcodeine in illicit
the body to codeine.
Ocfentanil in combination with caffeine and acetaminophen,
was reported in one previous seizure in the Netherlands in 2013,
where it was sold as ‘synthetic heroin’ [6]. Intoxications with other
fentanyl analogues and ‘heroin substitutes’ such as acetyl fentanyl,
butyrfentanyl, 4-fluorobutyrfentanyl and ß-hydroxythiofentanyl
are reported in recent literature [10–16]. Fentanyl or analogues
such as 3-methylfentanyl are known to be added in small amounts
in normal heroin [17], making them more potent and profitable.
Neither heroin nor other fentanyl analogues were detected in the
powder.
Internet searches carried out in July 2015 revealed a vendor
review posted on ‘DarkNetMarkets’ including results of presump-
tive tests (Mecke, Marquis, Mandelin, Froehde, Liebermann and
Gallic Acid) and GC/MS analysis carried out on a powder marketed
as ‘#40 and purchased as heroin. In the online review was
mentioned that a reference heroin was tested as control, that no
heroin was detected in the sample ‘#40 and the major constituents
found were in order of magnitude: acetaminophen, caffeine and
ocfentanil [18]. Widinos reported the presence of ocfentanil in 3
white powders and 3 brown powders recieved in the period March
2015–July 2015 [19]. The route of administration was stated
‘sniffing/snorting’ for 2 powders, ‘smoking’ for 1 powder and
‘unknown’ for the others. Three powders where profiled and found
to contain ocfentanil, caffeine and acetaminophen in varying
combinations, one containing mannitol and methamphetamine
respectively.

Table 2
Distribution of ocfentanil in the postmortem biological samples.

Biological sample Concentration ocfentanil

(mg/L of mg/kg)

Taken at the external body examination

Femoral blood (EDTA) 15.3
Vitreous humor 12.5
Mucous membrane of the nose Concentration above highest
calibrator (calculated value in
undiluted sample extract:
2999 ng/swab)
Taken at autopsy
Cardial blood (EDTA) 23.3
Cardial blood (without preservative) 21.9
Urine 6.0
Stomach content 17.1
Liver 31.2
Kidney 51.2
Brain tissue 37.9
Bile 13.7
Fig. 3. Chemical structure of fentanyl (A) and ocfentanil (B).
 V. Coopman et al. / Forensic Science International 266 (2016) 469–473
The reported ocfentanil fatality was an isolated case. No cluster
of intoxications were reported as seen in the past with NPS
entering the recreational drug scene as street or club drugs [20].
7. Conclusions
Ocfentanil is a new fentanyl anologue abused as NPS. This is the
first reported death involving this designer drug. Based on
circumstantial evidence, the autopsy findings and the results of
the toxicological analysis, the medical examiner concluded that
death was caused by an acute accidental intoxication with
ocfentanil after snorting powder containing the substance.
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