A fatal case of MAM-2201 poisoning

Saito, Takeshi; Namera, Akira; Miura, Naoya; Ohta, Shuji; Miyazaki, Shota; Osawa, Motoki; Inokuchi, Sadaki

doi:10.1007/s11419-013-0190-9

Cited by 80 publications

(66 citation statements)

References 13 publications

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“…MAM-2201 has been detected in recreational users and intoxication cases, when Tae Yeon Kong and Ju-Hyun Kim contributed equally to this work. plasma concentrations ranged from <0.1 to 49 ng/mL, indicating its extensive metabolism [19][20][21][25][26][27]. N-(5-hydroxypentyl)-MAM-2201, N-(4-hydroxyfluoropentyl)-MAM-2201, MAM-2201 pentanoic acid, and dealkyl-MAM-2201 have been identified as the metabolites of MAM-2201 in urine and hair samples from MAM-2201 abusers [27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Metabolic characterization of (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone (MAM-2201) using human liver microsomes and cDNA-overexpressed cytochrome P450 enzymes

et al. 2016

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MAM-2201 is a synthetic cannabinoid that is increasingly found in recreational drug abusers and cases of severe intoxication. Thus, characterization of the metabolic pathways of MAM-2201 is necessary to predict individual pharmacokinetics and toxicity differences, and to avoid toxic drug-drug interactions. Collectively, 19 phase 1 metabolites of MAM-2201 were identified using liquid chromatography-Orbitrap mass spectrometry following human liver microsomal incubations in the presence of NADPH: 7 hydroxy-MAM-2201 (M1-M7), 4 dihydroxy-MAM-2201 (M8-M11), dihydrodiol-MAM-2201 (M12), N-(5-hydroxypentyl)-MAM-2201 (M13), hydroxy-M13 (M14), N-dealkyl-MAM-2201 (M15), 2 hydroxy-M15 (M16, M17), MAM-2201 N-pentanoic acid (M18), and hydroxy-M18 (M19). On the basis of intrinsic clearance values in human liver microsomes, hydroxy-MAM-2201 (M1), N-(5-hydroxypentyl)-MAM-2201 (M13), and hydroxy-M13 (M14) were the major metabolites. Based on an enzyme kinetics study using human cDNA-expressed cytochrome P450 (CYP) enzymes and an immunoinhibition study using selective CYP antibodies in human liver microsomes, CYP1A2, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4 enzymes were responsible for MAM-2201 metabolism. The CYP3A4 enzyme played a prominent role in MAM-2201 metabolism, and CYP1A2, CYP2B6, CYP2C8, and CYP2C9 enzymes played major roles in the formation of some metabolites. MAM-2201 is extensively metabolized by multiple CYP enzymes, indicating that MAM-2201 and its metabolites should be used as markers of MAM-2201 abuse and toxicity. Graphical abstract In vitro metabolic pathways of MAM-2201 were characterized in human liver microsomes and recombinant CYPs using LC-HRMS analysis. Total 19 phase I metabolites were identified with predominant contribution of CYP3A4.

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Section: Introductionmentioning

confidence: 99%

Metabolic characterization of (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone (MAM-2201) using human liver microsomes and cDNA-overexpressed cytochrome P450 enzymes

et al. 2016

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“…Uygulama yolu ve dozu bilinme-yen MAM-2201 femoral kanda (1,24 µg/l), beyin, vücut organları ve adipoz dokuda tespit edilmiştir. 20 İsviçre'de 17 yaşında bir erkek sokakta yalnız ölü bulunmuştur. Arkadaşı, ölen gencin öl-meden önce iki nefes ot çektiğini, ellerinde uyuş-ma hissettiğini ve başının döndüğünü söylemiştir.…”

Section: Uygulanma şEkli Ve Toksisitesiunclassified

“…Türevlendirme işlemi için ekstrakt azot gazı kullanılarak kuruluğa kadar buhar-laştırılır (tamamen kurutulmuş olmalı ve su veya alkol kalıntısı olmamalı), türevlendirici eklenerek 70°C de 30 dk inkübe edip soğutulduktan sonra gaz kroma-tografikütle spektrometresine (GC/MS) verilir. [13][14][15][16][17][18][19][20][21][22][23][24]27 Sentetik kannabinoidleri tanımlamada ve biyoanalitik yöntemlerini geliştirmede karşılaşılan başlıca zorluklardan biri referans materyal eksikliğidir. Saf referans materyalin sınırlı olmasından dolayı bu maddelerin tanımlanması ve kantitatif analizinin yapılması zor olmaktadır.…”

Section: Sentetik Kannabinoidlerin Analizi Ve Karşılaşı-lan Zorluklarunclassified

Synthetic cannabinoids: A new generation marihuana

Dip¹,

Gülmen²,

Dağlioğlu³

et al. 2017

tahd

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“…Saito et al [42] reported the accumulation of some SCs such as MAM-2201 in the adipose tissue due to their high lipophilicity.…”

Section: Pharmacological and Toxicological Aspects Of Synthetic Cannamentioning

confidence: 99%

“…However, blood sampling requires the presence of medical staff for the collection and there being a risk of infection. [36], 5F-PB-22 [35], MAM-2201 [42], and ADB-CHMINACA [38], respectively. However, the lethal doses for many SCs are still unknown.…”

Section: Blood Serum and Plasmamentioning

confidence: 99%

Bioanalytical methods for the determination of synthetic cannabinoids and metabolites in biological specimens

Aldlgan

Torrance

2016

TrAC Trends in Analytical Chemistry

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Recently the use of synthetic cannabinoids (SCs) has increased around the world. As a result, the importance for accurate analysis of SCs in human biological matrices is evident and continues to be especially challenging due to their chemical structures being constantly modified. Many methods have been published recently for the analysis of SCs in human biological samples. This review provides an overview of the analytical methods used for the analysis of SCs and their metabolites in biological specimens with a special focus on chromatographic analysis and sample preparation.Liquid chromatography assay is the most commonly used for confirmation purposes of SCs and their metabolites in biological matrices. In blood and oral fluid, analysis of SCs must be very sensitive. In urine, SCs have extensive metabolism pathways; therefore the main target compounds are their hydroxyl and carboxyl metabolites, which is important to recognise when establishing clinical and forensic toxicology analytical methods.

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A fatal case of MAM-2201 poisoning

Cited by 80 publications

References 13 publications

Metabolic characterization of (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone (MAM-2201) using human liver microsomes and cDNA-overexpressed cytochrome P450 enzymes

Metabolic characterization of (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone (MAM-2201) using human liver microsomes and cDNA-overexpressed cytochrome P450 enzymes

Synthetic cannabinoids: A new generation marihuana

Bioanalytical methods for the determination of synthetic cannabinoids and metabolites in biological specimens

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