Analysis of UR-144 and its pyrolysis product in blood and their metabolites in urine

Adamowicz, Piotr; Zuba, Dariusz; Sekuła, Karolina

doi:10.1016/j.forsciint.2013.10.005

Cited by 59 publications

(67 citation statements)

References 26 publications

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“…Archiwum Medycyny Sądowej i Kryminologii Archives of Forensic Medicine and Criminology Z nielicznych prac eksperymentalnych [15][16][17] wynika, że metabolizm UR-144 przebiega poprzez hydroksylację i dalsze sprzęganie z kwasem glukuronowym i siarkowym, inne drogi metaboliczne obejmują m.in. dehydratację, hydroksylację, dealkilację, karboksylację.…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

“…Podobieństwo w mechanizmie działania poszczególnych syntetycznych kannabinoidów sprawia, że istnieje również podobieństwo w efektach działania między UR-144 a JWH-122 i AM-2201 czy marihuaną. Obejmują one takie odScarce experimental studies [15][16][17] demonstrate that UR-144 is metabolized by hydroxylation and further conjugation with glucuronic and sulphuric acids. Other metabolic routes include dehydration, hydoxylation, dealkylation and carboxylation.…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

“…They include sensations such as euphoria, mood eleva- czucia, jak euforia, podniesienie nastroju, podniecenie, relaks, wesołość, zwiększony apetyt, a następnie senność i halucynacje. Mogą wystąpić także efekty uboczne -niepokój, zaburzenia równowagi, odczucia paranoiczne, depresja, halucynacje, które niekiedy utrzymują się nawet kilka dni [14,[17][18][19]. Kronstrand [18] uważa, że efekty uboczne występujące po paleniu marihuany są z reguły łagodne, natomiast efekty uboczne po paleniu syntetycznych kannabinoidów pojawiają się często i obejmują wzrost ciśnienia krwi, niepokój, podniecenie, halucynacje, psychozy, ataki paniki, a nawet utratę przytomności.…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

“…W piśmiennictwie jest kilka opisów przypadków raportowanych jako zatrucia, także UR-144 [17][18][19][20].…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

“…Ponadto w przypadkach o ciężkim przebiegu klinicznym powodowanym przez syntetyczne kannabinoidy można mówić o efekcie abstynencyjnym w uzależnieniu od tego typu narkotyków [23]. Pod względem farmakologicznym i toksykologicznym UR-144 jest słabo poznany, jednak pewne informacje wskazują, że zażycie UR-144 może się wiązać z wystąpieniem różnego rodzaju zaburzeń psychicznych, często w postaci stanów lęko-wych, dysforycznych, depresyjnych, psychotycznych czy omamów, podczas których, jak wynika z wyżej cytowanych prac [17][18][19], istnieje ryzyko targnięcia się na własne życie.…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

See 4 more Smart Citations

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Rojek¹,

Korczyńska-Albert²,

Kulikowska³

et al. 2017

amsik

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Section: By Lc-esi-ms-ms In Blood Samplesunclassified

“…W piśmiennictwie jest kilka opisów przypadków raportowanych jako zatrucia, także UR-144 [17][18][19][20].…”

Section: By Lc-esi-ms-ms In Blood Samplesunclassified

See 3 more Smart Citations

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Rojek¹,

Korczyńska-Albert²,

Kulikowska³

et al. 2017

amsik

View full text Add to dashboard Cite

Quantitative urine confirmatory testing for synthetic cannabinoids in randomly collected urine specimens

Castaneto

Scheidweiler

Gandhi

et al. 2014

Drug Testing and Analysis

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Synthetic cannabinoid intake is an ongoing health issue worldwide, with new compounds continually emerging, making drug testing complex. Parent synthetic cannabinoids are rarely detected in urine, the most common matrix employed in workplace drug testing. Optimal identification of synthetic cannabinoid markers in authentic urine specimens and correlation of metabolite concentrations and toxicities would improve synthetic cannabinoid result interpretation. We screened 20,017 randomly collected US military urine specimens between July 2011 and June 2012 with a synthetic cannabinoid immunoassay yielding 1,432 presumptive positive specimens. We analyzed all presumptive positive and 1,069 negative specimens with our qualitative synthetic cannabinoid LC-MS/MS method, which confirmed 290 positive specimens. All 290 positive and 487 randomly-selected negative specimens were quantified with the most comprehensive urine quantitative LC-MS/MS method published to date. 290 specimens confirmed positive for 22 metabolites from 11 parent synthetic cannabinoids. The five most predominant metabolites were JWH-018 pentanoic acid (93%), JWH-018 N-hydroxypentyl (84%), AM2201 N-hydroxypentyl (69%), JWH-073 butanoic acid (69%), and JWH-122 N-hydroxypentyl (45%) with 11.1 (0.1–2434), 5.1 (0.1–1239), 2.0 (0.1–321), 1.1 (0.1–48.6), and 1.1 (0.1–250) μg/L median (range) concentrations, respectively. Alkyl hydroxy and carboxy metabolites provided suitable biomarkers for 11 parent synthetic cannabinoids; although, hydroxyindoles also were observed. This is by far the largest data set of synthetic cannabinoid metabolites urine concentrations from randomly collected workplace drug testing specimens rather than acute intoxications or driving under the influence of drugs. These data improve the interpretation of synthetic cannabinoid urine test results and suggest suitable urine markers of synthetic cannabinoid intake.

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Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue

Sobolevsky¹,

Prasolov²,

Rodchenkov³

2014

Drug Testing and Analysis

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The data are reported for an in vitro metabolism study of two novel synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and its fluorinated analog N-(1-adamantyl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (5F-APICA, STS-135), which are active ingredients of smoking mixtures sold in Russia since 2012. The cannabinoids were isolated from herbal mixtures using preparative liquid chromatography and then incubated with human liver microsomes (HLMs). The formed metabolites were characterized by liquid chromatography - triple quadrupole mass spectrometry and high-resolution mass spectrometry with electrospray ionization in positive ion mode. It was found that HLMs produce mono-, di-, and trihydroxylated metabolites, as well as N-desalkyl metabolites, which can be further hydroxylated; the amide bond resisted the metabolic cleavage. For 5F-APICA, a series of oxidative defluorination products formed as well. For in vivo confirmation of the formed in vitro metabolites, spot urine samples from drug users were analyzed with the created method. It was shown that for the detection of APICA abuse, the preferred metabolites are the di- and tri-hydroxylated species, while in case of 5F-APICA, a monohydroxy metabolite is a better target. The N-despentyl (desfluoropentyl) hydroxyadamantyl metabolite also provides good retrospectivity to confirm the administration of any of these cannabinoids.

show abstract

Analysis of UR-144 and its pyrolysis product in blood and their metabolites in urine

Cited by 59 publications

References 26 publications

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

New challenges in toxicology of new psychoactive substances exemplified by fatal cases after UR-144 and UR-144 with pentedrone administration determined by LC-ESI-MS-MS in blood samples

Quantitative urine confirmatory testing for synthetic cannabinoids in randomly collected urine specimens

Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue

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