synthetic cathinone stability in urine using...
TRANSCRIPT
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Synthetic Cathinone Stability in Urine Using LC/Q-TOF-MS
Lindsay Glicksberg, BS; Sarah Kerrigan, PhD
Department of Forensic ScienceSam Houston State University
Huntsville, TX, USA
46th Annual SOFT, Dallas, 20161
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DISCLOSURE
The authors have no commercial disclosure
Project funded by NIJ Award # 2013-R2-CX-K006
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SYNTHETIC CATHINONE BACKGROUND
• Derived from cathinone, a naturally occurring compound in the leaves of the Catha edulis shrub
• Synthetic cathinones synthesized for the same effects
• Effects similar to methamphetamine and MDMA
• Available on the internet and in head shops with labels such as:
“not for human consumption”
“bath salts”
“Plant food”
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PHARMACOLOGY AND TOXICOLOGY
Desired Effects:
stimulant and euphoric symptoms
Increased energy, mood enhancement, empathy, sociability, concentration, euphoria
Adverse Effects:
neurological, cardiovascular, and psychopathological symptoms
Hallucinations, delusions, confusion, violence, homicidal tendencies, death
Antemortem Cases: Motor Vehicle Accidents & Driving While Impaired
Postmortem Cases: Overdose, Suicide, Homicide
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GENERAL STRUCTURE OF CATHINONE
Phenethylamines
R groups represent positions that can be substituted to create various synthetic cathinones
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IMPORTANCE OF STABILITY
Understanding the stability of a drug in biological matrices in essential
Condition and length of storage can affect drug concentration
Specimens stored for days, weeks, or months prior to analysis
Subjected to various conditions during collection and shipping process
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CATHINONE INSTABILITY
Plant Material
Unstable in oxygen rich conditions (Szendrei, 1980)
Unstable in alkaline conditions (Szendrei, 1980; Berrang, 1982)
Dimer formation (Berrang, 1982; Chappell, 2010)
Best to air dry and refrigerate
Thermal Degradation
Thermal degradation in GC-MS
Methcathinone (DeRuiter, 1994)
α-PVP (Tsujikawa, 2013)
19 synthetic cathinones (Kerrigan, 2015)
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BIOLOGICAL MATERIAL
Paul and Cole (2001): Cathinone/Methcathinone
Urine
-18°C and 4°C
3 months
-18°C: stable for 2 months
4°C: stable for 3 days, unstable for 3 months
Sorensen (2011): Methcathinone, Ethcathinone,
Mephedrone, Flephedrone, Methedrone,
Methylone, Butylone
Blood (pH 7.4 and 5.9)
5°C and 20°C
7 days
More stable in pH 5.9 and 5°C over 7 day
period
Tsujikawa (2012): Methcathinone, Mephedrone, 3-
FMC, 4-FMC, Ethcathinone
Aqueous pH solutions
More stable at acidic pH,
decomposition rate dependent
upon chemical structure
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BIOLOGICAL MATERIAL
Johnson and Botch-Jones
(2013): MDPV/Mephedrone
Blood, Plasma, Urine
-20°C, 4°C, 22°C
14 days
-20°C: stable in 3 matrices
Mephedrone unstable at 4°C and 22°C
Soh and Elliott (2014): 4-MEC
Blood and Plasma
20°C and 5°C
7 days
Unstable at both temperature
Busardo (2016): Mephedrone
Antemortem & Postmortem
Blood
-20°C, 4°C, 20°C
6 months
Unstable at 4°C and 20°C by
3 months
Stable at -20°C
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STABILITY STUDIES
Previous stability studies have been reported, however…
No systematic and fully comprehensive study addressing synthetic
cathinone stability in biological evidence
22 synthetic cathinones
1 biological matrices
4 temperatures
>6 months
Comprehensive study assessing stability as it relates
1. pH
2. Concentration
3. Temperature
4. Storage time
5. Chemical properties 10
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RESEARCH DESIGN
11
-20°C
-20°C
-20°C
-20°C
100 ng/mL 100 ng/mL
1000 ng/mL1000 ng/mL
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LC/Q-TOF-MS CONDITIONS
LC Separation
Poroshell 120 EC-C18 Column (2.1x100mm, 2.7 µm particle size)
Mobile Phase A: 0.1% FA in diH2O
Mobile Phase B: 0.1% FA in ACN
Flow Rate: 0.40 mL/min
LC Gradient:
96% A to 5 min, 90% A until 11 min, 60% A for 1 min, 0% A to equilibrate the column
Q/TOF Parameters
Gas Temperature: 200°C
Gas Flow Rate: 13 L/min
Sheath Gas Temperature: 250°C
Sheath Gas Flow Rate: 12 L/min
Nebulizer Pressure 20 psig
Mass Spectrometry Capillary Voltage: 4000 V
Fragmentor Voltage: 150 V
Nozzle Voltage: 0 V
Collision Energy: 30 eV, 20 eV MS Scan Rate: 8 spectra/sec
MS/MS Scan Rate: 3 spectra/sec
MS Scan Range: 40-1000 m/z
ESI Mode: Positive
Acquisition Minimum of two ion
transitions per drug
Run Time: 13 minutes
Agilent Technologies 6530 Accurate-Mass Q-TOF LC/MS
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LC/Q-TOF EIC
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VALIDATION SUMMARY
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SWGTOX Standard Practices for Method Validation
LOD: 0.25 – 5 ng/mL
LOQ: 0.25 – 5 ng/mL
Precision: ±15%
Bias: ±15%
Accuracy: 84 – 104%
Matrix Effects: ± 20%
Dilution Integrity: 2- and 4- fold
Interferences: No interferences (>50 interferents)
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STABILITY STUDY ANALYSIS
Extraction
Urine samples in duplicate
(n=2)
1000 ng/mL samples 1:4
dilution
Calibrators extracted with
every run
10, 25, 100, 250, 350, and
500 ng/mL
Negative and Positive (100
ng/mL) Controls
Analysis
Concentration Mean
(n=2)
Error bars emitted for
clarity
Significant >20% loss
Month Samplings/Week
1 4
2-3 2-3*
4-6 1
6-12 1/month
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SECONDARY AMINES, NO RING SUBSTITUENTS
Methcathinone Ethcathinone Buphedrone Pentedrone
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SECONDARY AMINES, RING SUBSTITUTED
Mephedrone* 4-MEC 4-EMC Methedrone
Flephedrone 3-FMC 3,4-DMMC
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SECONDARY AMINES, METHYLENEDIOXY TYPE
Methylone* Ethylone* Butylone*
Pentylone* Eutylone*
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TERTIARY AMINES, PYRROLIDINE TYPE
Alpha-PVP* MPBP Pyrovalerone Naphyrone*
MDPV* MDPBP
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CHEMICAL STRUCTURE DEPENDENCE:
20
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
Methcathinone
Ethcathinone
Buphedrone
Pentedrone
3-FMC
4-FMC
Methedrone
Mephedrone
4-MEC
3,4-DMMC
4-EMC
Methylone
Ethylone
Butylone
Eutylone
Pentylone
MDPBP
alpha-PVP
MPBP
MDPV
Pyrovalerone
Naphryone
pH 8 urine, 100 ng/mL, 4°C
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TEMPERATURE DEPENDENCE (PH 4, 100 NG/ML)
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
Days
4°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165Days
-20°C
21
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
32°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
20°C
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TEMPERATURE DEPENDENCE (PH 8, 100 NG/ML)
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
32°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
20°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
Days
4°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165Days
-20°C
22
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PH DEPENDENCE (100 NG/ML)
pH 4
pH 8
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
23
32°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
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PH DEPENDENCE(100 NG/ML)
pH 4
pH 8
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
24
20°C
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
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PH DEPENDENCE(100 NG/ML)
pH 4
pH 8
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
25
4°C
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PH DEPENDENCE(100 NG/ML)
pH 4
pH 8
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
26
-20°C
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CONCENTRATION DEPENDENCE
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
pH 4, 1000 ng/mL
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165Days
pH 8, 1000 ng/mL
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
Days
pH 8, 100 ng/mL
27
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et
(%)
pH 4, 100 ng/mL
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DAYS TO >20% LOSS
Cathinone
Structural Group
32°C 20°C 4°C -20°C
pH 4 pH 8 pH 4 pH 8 pH 4 pH 8 pH 4 pH 8
Ring Substituted 7-78 <1 24 - >172 ≤1 >172 1-5 >172 3-12
Unsubstituted 21-68 <1 42-115 ≤1 >172 1-5 >172 7-19
Methylenedioxy 68-143 ≤1 >172 1-3 >172 5-21 >172 16 - >172
Pyrrolidine >143 1-14 >172 3-42 >172 19 - >172 >172 16 - >172
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-20°C INSTABILITY
Ring Substituted: <2 weeks
Ring Substituted: >6 months
Unsubstituted: 1-3 weeks
Unsubstituted: >6 months
Methylenedioxy: >6 months
Pyrrolidine: >6 months
29
1 month 2 months 3 months 4 months 5 months 6 months
Methylenedioxy: 2 weeks - >6 months
Pyrrolidine: 2 weeks - >6 months
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4°C INSTABILITY
Ring Substituted: <1 week
Methylenedioxy: < 3 weeks
Ring Substituted: >6 months
Unsubstituted: <1 week
Unsubstituted: >6 months
Methylenedioxy: >6 months
Pyrrolidine: >6 months
30
1 month 2 months 3 months 4 months 5 months 6 months
Pyrrolidine: 3 weeks - > 6 months
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20°C INSTABILITY
Ring Substituted: ≤1 day
Methylenedioxy: 1-3 days
Ring Substituted: 3 weeks - > 6 months
Unsubstituted: ≤1 day
Unsubstituted: 1.5 – 4 months
Methylenedioxy: >6 months
Pyrrolidine: >6 months
31
1 month 2 months 3 months 4 months 5 months 6 months
Pyrrolidine: <1.5 mo
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32°C INSTABILITY
Ring Substituted: <1 day
Methylenedioxy: ≤1 day
Pyrrolidine: < 2 weeks
Ring Substituted: 1 wk. – 2.5 mo.
Unsubstituted: <1 day
Unsub:
3 wks – 2.5 mo.
Methylenedioxy: 2.5 – 5 mo.
PYR: >5 mo.
32
1 month 2 months 3 months 4 months 5 months 6 months
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CONCLUSIONS
pH Dependence
Acidic > Alkaline
Temperature Dependence
-20°C > 4°C > 20°C > 32°C
No Concentration Dependence
Significant Structural Dependence
MD/PYR > PYR > MD > Ring Substituted > Unsubstituted > 3-FMC
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CONCLUSIONS
Significant loss on the order of hours (alkaline urine, 32°C and 20°C)
3-FMC: 32°C—undetectable after 6 hours
Substituted and Unsubstituted
32°C: 20-88% loss after 6 hours
20°C: 21-89% loss after 22 hours
Instability at common storage conditions (4°C)
Significant Structural Influence34
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
pH 8
0%
20%
40%
60%
80%
100%
120%
0 15 30 45 60 75 90 105 120 135 150 165
Targ
et (
%)
Days
pH 4
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ACKNOWLEDGEMENTS
This project was supported by Award No. 2013-R2-CX-K006 awarded by the National Institute of Justice, Office of Justice Programs, U.S. Department of Justice. The opinions, findings, and conclusions or recommendations expressed in this publication are those of the author(s) and do not necessarily reflect those of the Department of Justice.
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