Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays

Nakajima, Jun; Takahashi, Misako; Nonaka, Ryouichi; Seto, Takako; Suzuki, Jin; Yoshida, Masao; Kanai, Chieko; Hamano, Tomoko

doi:10.1007/s11419-011-0114-5

Cited by 91 publications

(67 citation statements)

References 19 publications

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“…Beginning in October 2012, new type of synthetic cannabinoids, a structural modification of compounds from 3-naphthoylindole series [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] has begun to be seized by police regularly, on the territory of Russia and Belarus.…”

Section: Introductionmentioning

confidence: 99%

Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid

Шевырин

Melkozerov²,

Nevero³

et al. 2013

Forensic Science International

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Section: Introductionmentioning

confidence: 99%

Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid

Шевырин

Melkozerov²,

Nevero³

et al. 2013

Forensic Science International

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“…For example, PINACA compounds appear on the market as APINACA (AKB-48) and ADB-PINACA together within a mixture alongside the 5-fluoropentyl analogs. [7][8][9][10][11] PB-22 and 5F-PB-22 were first reported as the drugs in a 2009 patent filed by the pharmaceutical manufacturer Pfizer.…”

Section: Chemistrymentioning

confidence: 99%

How Present Synthetic Cannabinoids Can Help Predict Symptoms in the Future

Mozayani¹

2016

MOJT

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Abbreviations: SCs, synthetic cannabinoids; Δ-9-THC, delta-9-tetrahydracannabinol; UHPLC, ultra high performance liquid chromatography; DAD, photodiode array; MS, mass spectrometry; GC, gas chromatography; DART, direct analysis in real time; TOF, time of flight spectrometry; NMR, nuclear magnetic resonance; ATR, attenuated total resonance; FTIR, fourier transform infrared spectrometry; TIC, total ion chromatogram; LC-MS/MS, liquid chromatography tandem mass spectrometry; CNS, central nervous system; LOD, limit of detection; LOQ, limit of quantitation; ULOL, upper limit of linearity; DUID, driving under the influence of drug; HLM, human liver microsomes; HPM, human pulmonary microsomes; CES 1, carboxylesterase 1 IntroductionSynthetic cannabinoids (SCs) are synthetic compounds sprayed on herbal products and have spread worldwide since 2004. Many of these compounds, more specifically l-valinamides and l-tert-leucinamides, are often characterized as part of the third, fourth and fifth generation of synthetic cannabinoids. There are many street names for herbal like compounds which are sprayed with these compounds, referred to as "Spice" such as Spice Diamond, Spice Gold, Spice Arctic Energy, Magic, Voodoo and Yucatan Fire. Such drugs are easily obtainable via the Internet, in smoke shops, and street markets. To evade law enforcement, these herbal incense products are often labeled "not for human consumption". Despite this, many countries have entered many synthetic cannabinoids to schedule 1. 1,2Initial reports of synthetic cannabinoids (SCs) in Unites States were in November 2008. In December 2008, German forensic laboratories initially identified JWH-018 and cannabicyclohexanol (CP-47,497 C8 homologue). The synthetic cannabinoids are frequently applied on plant material and inhaled. In January 2010, the popularity of these cannabinoids and their associated products appeared to have increased in the United States.3 Numerous SCs have been identified as adulterants, which have been seized by law enforcement. JWH-018, JWH-073, JWH-200, CP-47,497, and CP-47,497 C8 homologues were the first SCs identified as being abused. New generations of synthetic cannabinoids quickly emerged to evade law enforcement. After various laws were passed in the United States, different generations of SCs emerged varying only by slight modifications in structure. Some recent SCs include AB-CHMINACA and AB-PINACA. These substances are commonly marketed under the guise of being a ''legal high'' with a disclaimer of ''not for human consumption''. Law enforcement, public health officials, and clinicians are encountering cases in which there has been abuse of these substances, 4 requiring up to date information of the drug legislation, chemistry of the compounds and their detection, as well as the toxicology to be able to help identify these compounds when they present clinically.After the passage of the Synthetic Drug Abuse Prevent Act of 2012 in the United States, a third and fourth generation of SCs including UR-144, XLR11, and AKB-48 emerged...

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“…Structure-activity relationships for synthetic cannabinoids have been established [4][5][6][7][8], and JWH compounds (JWH-018, JWH-122, and JWH-073) have been modified as follows: introduction of a fluorine atom (AM-2201, MAM-2201, and EAM-2201) [9] and substitution of the naphthyl group for a cyclopropyl group (UR-144 and XLR-11) [10,11], adamantyl group (APICA and 5F-APICA) [10], or quinolinyl group (QUPIC and QUCHIC) [12,13]. Synthetic cannabinoids have been found in seized herbal materials, and their continual emergence on recreational and illicit drug markets has become a global issue [14][15][16][17][18][19].…”

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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Abstract: During our careful surveillance of unregulated

Cited by 91 publications

References 19 publications

Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid

Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid

How Present Synthetic Cannabinoids Can Help Predict Symptoms in the Future

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

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