Identification of Designer Drug 2C-E (4-Ethyl-2, 5-Dimethoxyphenethylamine) in Urine Following a Drug Overdose

Vrancken, Michael J. Van; Benavides, Raul; Wians, Frank H.

doi:10.1080/08998280.2013.11928922

Cited by 7 publications

(6 citation statements)

References 17 publications

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“…Although some of these cases occurred due to adulteration of samples with a high potency compound such as DOB-DFLY (Chavarin et al 2013; Iwersen-Bergmann et al 2018), in other cases the phenylethylamines themselves were the causative agents (Curtis et al 2003; Drees et al 2009; Topeff et al 2011; Sacks et al 2012; Bosak et al 2013; Van Vrancken et al 2013; Stoller et al 2017). In addition to 2C-B and 2C-I, which are popular phenethylamine hallucinogens (de Boer and Bosman 2004; Caudevilla-Galligo et al 2012; Burns et al 2014), 4-ethyl-2,5-dimethoxyphenethylamine (2C-E) is also used recreationally (Topeff et al 2011; Sacks et al 2012; Van Vrancken et al 2013; Woo and Hanley 2013). According to Shulgin and Shulgin (1991), 2C-E is active at doses of 10–25 mg. 4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine (2C-EF) also reportedly acts as a hallucinogen and is orally active in humans at doses of 6–12 mg with a duration of 12 hours (Shulgin et al 2011), although information about the extent of recreational use of this substance appears to be lacking.…”

Section: Discussionmentioning

confidence: 99%

Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran (“FLY”) and benzodifuran (“DragonFLY”) analogs

et al. 2019

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In recent years, rigid analogues of phenylalkylamine hallucinogens have appeared as recreational drugs. Examples include 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)ethan-1-amine (2C-B-FLY) and 1-(8-bromobenzo[1,2-b;4,5-b ’]difuran-4-yl)-2-aminopropane (Bromo-DragonFLY, DOB-DFLY). Although some rigid compounds such as DOB-DFLY reportedly have higher potency than their non-rigid counterparts, it is not clear whether the same is true for 2C-B-FLY and other tetrahydrobenzodifurans. In the present study, the head twitch response (HTR), a 5-HT2A receptor-mediated behavior induced by serotonergic hallucinogens, was used to assess the effects of 2,5-dimethoxy-4-bromoamphetamine (DOB) and its α-desmethyl homologue 2,5-dimethoxy-4-bromophenethylamine (2C-B), as well as their benzodifuranyl and tetrahydrobenzodifuranyl analogs, in C57BL/6J mice. DOB (ED50 = 0.75 μmol/kg) and 2C-B (ED50 = 2.43 μmol/kg) induced the HTR. The benzodifurans DOB-DFLY (ED50 = 0.20 μmol/kg) and 2C-B-DFLY (ED50 = 1.07 μmol/kg) had significantly higher potency than DOB and 2C-B, respectively. The tetrahydrobenzodifurans DOB-FLY (ED50 = 0.67 μmol/kg) and 2C-B-FLY (ED50 = 1.79 μmol/kg), by contrast, were approximately equipotent with their non-rigid counterparts. Three novel tetrahydrobenzodifurans (2C-I-FLY, 2C-E-FLY and 2C-EF-FLY) were also active in the HTR assay but had relatively low potency. In summary, the in vivo potency of 2,5-dimethoxyphenylalkylamines is enhanced when the 2- and 5-methoxy groups are incorporated into aromatic furan rings, whereas potency is not altered if the methoxy groups are incorporated into dihydrofuran rings. The potency relationships for these compounds in mice closely parallel the human hallucinogenic data. The high potency of DOB-DFLY is probably linked to the presence of two structural features (a benzodifuran nucleus and an α-methyl group) known to enhance the potency of phenylalkylamine hallucinogens.

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Section: Discussionmentioning

confidence: 99%

Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran (“FLY”) and benzodifuran (“DragonFLY”) analogs

et al. 2019

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“…In addition, the adverse effects we observed in rat and mouse behavioral assays included tremor, muscle spasms, hind limb paralysis and lethality and indicate toxicity at higher doses. Recent reports of seizures and serotonin syndrome following 2C-I ingestion (Bosak et al 2013), fatal toxic leukoencephalopathy and acute kidney failure following 2C-E ingestions (Sacks et al 2012;Van Vrancken et al 2013), and seizures and rhabdomyloysis following DOC and MDMA co-ingestion (Ovaska et al 2008) suggest consumption of these phenethylamines carries significant health risk.…”

Section: Discussionmentioning

confidence: 99%

Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function

et al. 2013

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Rationale Psychoactive substituted phenethylamines 2,5-dimethoxy-4-chlorophenethylamine (2C-C); 2,5-dimethoxy-4-methylphenethylamine (2C-D); 2,5-dimethoxy-4-ethylphenethylamine (2C-E); 2,5-dimethoxy-4-iodophenethylamine (2C-I); 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and 2,5-dimethoxy-4-chloroamphetamine (DOC) are used recreationally and may have deleterious side effects. Objectives This study compares behavioral effects and mechanisms of action of these substituted phenethylamines with those of hallucinogens and a stimulant. Methods The effects of these compounds on mouse locomotor activity and in rats trained to discriminate dimethyltryptamine, (−)DOM, (+)LSD, (±)MDMA and (S+)methamphetamine were assessed. Binding and functional activity of the phenethylamines at 5-HT1A, 5-HT2A, 5-HT2C receptors and monoamine transporters were assessed using cells heterologously expressing these proteins. Results The phenethylamines depressed mouse locomotor activity, although 2C-D and 2C-E stimulated activity at low doses. The phenethylamines except 2C-T-2 fully substituted for at least one hallucinogenic training compound but none fully substituted for (+)-methamphetamine. At 5-HT1A receptors, only 2C-T-2 and 2C-I were partial-to-full very low potency agonists. In 5-HT2A arachidonic acid release assays, the phenethylamines were partial to full agonists except 2C-I which was an antagonist. All compounds were full agonists at 5-HT2A and 5-HT2C receptor inositol phosphate assays. Only 2C-I had moderate affinity for, and very low potency at, the serotonin transporter. Conclusions The discriminative stimulus effects of 2C-C, 2C-D, 2C-E, 2C-I and DOC were similar to those of several hallucinogens but not methamphetamine. Additionally, the substituted phenethylamines were full agonists at 5-HT2A and 5-HT2C receptors, but for 2C-T-2, this was not sufficient to produce hallucinogenlike discriminative stimulus effects. Additionally, the 5-HT2A inositol phosphate pathway may be important in 2C-I’s psychoactive properties.

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“…Apart from multiple fatalities due to NBOMes, namely 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe (for a review, see [39]), fatalities have also been associated with other novel SPs, e.g. tryptamines (AMT, 5-MeO-AMT, AET, 5-OH-DMT [68]) and derivatives of the phenethylamine groups 2C-x (2C-E [69,70], 2C-T-7, 2C-T-21 [71]) and DOx (DOB, DOC [62,72], Bromo-DragonFLY [73]) (see list of abbreviations). Even if the exact toxicological mechanisms are not well understood in humans, animal studies indicate neuro-and genotoxic properties of certain SPs, such as 5-MeO-DIPT [74], 2C-C, 2C-P [75], and 25B-NBOMe [76,77].…”

Section: Harms Associated With Serotonergic Psychedelicsmentioning

confidence: 99%

Safer Tripping: Serotonergic Psychedelics and Drug Checking. Submission and Detection Rates, Potential Harms, and Challenges for Drug Analysis

et al. 2021

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Purpose of Review With the continuous emergence of new psychoactive substances, drug checking (DC) services are challenged by an increasingly complex drug market. Considering the resumed scientific and public interest in serotonergic psychedelics (SPs) like LSD, psilocybin, and 2C-B, we present the results of a literature search investigating the presence and proportion of SPs in DC samples. Recent Findings In 15 identified reports, submission and detection rates of SPs were comparably low, but increasing. Samples contained considerable amounts of adulterations or analogues, mostly novel SPs with unknown toxicological profiles and in some cases potentially life-threatening effects. The detection of SPs, however, requires advanced analysis techniques currently not available to most DC services. Summary Given the substantial proportion of novel SPs in DC samples and the associated risks, DC can be a valuable harm reduction and monitoring tool for SPs if analysis techniques with high sensitivity are employed.

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Identification of Designer Drug 2C-E (4-Ethyl-2, 5-Dimethoxyphenethylamine) in Urine Following a Drug Overdose

Cited by 7 publications

References 17 publications

Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran (“FLY”) and benzodifuran (“DragonFLY”) analogs

Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran (“FLY”) and benzodifuran (“DragonFLY”) analogs

Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function

Safer Tripping: Serotonergic Psychedelics and Drug Checking. Submission and Detection Rates, Potential Harms, and Challenges for Drug Analysis

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