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Fluorexetamine
Fluorexetamine
Fluorexetamine
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from Wikipedia
Fluorexetamine
Legal status
Legal status
Identifiers
  • 2-(ethylamino)-2-(3-fluorophenyl)cyclohexan-1-one
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H18FNO
Molar mass235.302 g·mol−1
3D model (JSmol)
  • CCNC1(CCCCC1=O)c1cccc(F)c1
  • InChI=1S/C14H18FNO/c1-2-16-14(9-4-3-8-13(14)17)11-6-5-7-12(15)10-11/h5-7,10,16H,2-4,8-9H2,1H3
  • Key:FCETYWCLCUZFJI-UHFFFAOYSA-N

Fluorexetamine (3'-fluoro-2-oxo-PCE, 3-FXE) is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It has reportedly been sold over the internet since around 2017, though has remained relatively uncommon.[1]

In April 2023 it was revealed by DrugsData.org that all their previously analyzed samples of fluorexetamine actually contained 2'-fluoro-2-oxo-PCE (2-FXE, also known as CanKet) rather than 3'-fluoro-2-oxo PCE (3-FXE). This was confirmed by a newly available reference standard for 2-FXE.[2] Similar misidentification may have occurred in other laboratories.

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Fluorexetamine

View on Grokipedia
from Grokipedia
Fluorexetamine (FXE), chemically known as 2-(ethylamino)-2-(3-fluorophenyl)cyclohexan-1-one, is a synthetic arylcyclohexylamine classified as a novel dissociative and hallucinogenic substance. Its structure features a cyclohexanone core attached to a meta-fluorinated phenyl ring and an ethylamino group, differentiating it from ketamine through the fluorine substitution and extended amine chain length. As a designer drug, fluorexetamine has emerged in recreational markets, primarily distributed online, where it induces dissociative anesthesia, analgesia, and perceptual distortions similar to ketamine and phencyclidine. Limited empirical data exist due to its status as a new psychoactive substance outside regulated research, with user reports indicating slightly more stimulating effects alongside risks of mania and co-ingestion complications akin to established dissociatives. Analytical standards confirm its identity for forensic and toxicological purposes, underscoring its detection in novel drug monitoring efforts.

Chemistry

Chemical Structure and Synthesis

Fluorexetamine, systematically named 2-(ethylamino)-2-(3-fluorophenyl)cyclohexan-1-one, possesses a molecular formula of C₁₄H₁₈FNO and a of 235.3 g/mol. This compound belongs to the class, characterized by a core with substitution at the 2-position by an ethylamino (-NHCH₂CH₃) group and a 3-fluorophenyl ring. The atom at the meta position of the phenyl ring distinguishes it from , which features a methylamino group and a 2-chlorophenyl , while sharing the alpha-amino motif with other analogs like eticyclidone. The structural scaffold derives from phencyclidine (PCP), but incorporates a ketone functionality akin to ethylaminoketones, enhancing its relation to derivatives. The 3-fluorophenyl substitution introduces electronic effects that may influence reactivity compared to unsubstituted phenyl analogs, though specific computational or empirical data on bond lengths or angles remain limited in public chemical databases. Synthesis of fluorexetamine generally proceeds via multi-step routes starting from and 3-fluorobromobenzene or related halides. A common pathway involves Grignard addition: reacts with 3-fluorophenylmagnesium bromide to yield 1-(3-fluorophenyl)cyclohexan-1-ol, followed by oxidation to 1-(3-fluorophenyl)cyclohexan-1-one, alpha-halogenation (e.g., bromination), and nucleophilic displacement with to install the ethylamino group. Alternative approaches may employ on the alpha-keto intermediate or variations using rearrangements, analogous to production methods, though optimized conditions for the fluoro-substituted aryl are not detailed in peer-reviewed literature. Clandestine syntheses often adapt these routes, resulting in impure products due to incomplete purification steps like or . No industrial-scale processes have been reported, reflecting its status as a .

Physical and Chemical Properties

Fluorexetamine, chemically 2-(2-fluorophenyl)-2-(ethylamino)cyclohexan-1-one, possesses the molecular formula C14H18FNO for the form, with a computed molecular weight of 235.30 g/mol. The salt, which is the predominant form in analytical references, has the formula C14H18FNO · HCl and a molecular weight of approximately 271.76 g/mol. It appears as a crystalline , typically white or off-white in pure form. data indicate moderate in polar organic solvents and aqueous buffers: 10 mg/mL in DMSO and , 5 mg/mL in DMF and ( 7.2). These properties facilitate its handling in settings but highlight limited in non-polar solvents without further solubilization. Under recommended storage at -20°C, the salt exhibits stability for at least 5 years, with no significant degradation reported in controlled conditions. Impure samples, as may arise from non-pharmaceutical synthesis, could show reduced stability due to potential or oxidation of the and functionalities, though specific degradation kinetics remain undocumented in peer-reviewed literature.

Pharmacology

Mechanism of Action

Fluorexetamine functions primarily as a non-competitive antagonist at N-methyl-D-aspartate (NMDA) receptors within the arylcyclohexylamine class of dissociatives, a mechanism shared with ketamine and phencyclidine that inhibits glutamate-induced cation influx and disrupts excitatory neurotransmission in the central nervous system. This antagonism occurs at the phencyclidine (PCP) binding site within the NMDA receptor ion channel, reducing synaptic plasticity and contributing to anesthetic and dissociative properties observed in structural analogs. Direct empirical data on Fluorexetamine's receptor binding affinities are absent from peer-reviewed literature as of 2025, with pharmacological characterization relying on structural analogies to fluorinated ketamine derivatives like (2-FDCK). The 3'-fluoro substitution on the phenyl ring and 2-oxetanyl group may enhance or alter steric interactions at the NMDA site compared to unsubstituted PCE analogs, potentially influencing potency, though no assays confirm differential binding kinetics or selectivity. Arylcyclohexylamines like Fluorexetamine exhibit off-target effects at sigma-1 receptors and, to lesser extents, μ- and κ- receptors, which could modulate analgesia but remain understudied for this compound; fluorine modifications in analogs have been associated with preserved or slightly reduced affinity relative to . No verified interactions with serotonin systems, such as 5-HT2A agonism, have been reported, distinguishing it from serotonergic hallucinogens despite occasional user-reported stimulation. The absence of animal or human pharmacokinetic studies precludes quantification of these pathways' contributions to overall activity.

Pharmacokinetics and Metabolism

Fluorexetamine, a fluorinated analog of , lacks comprehensive pharmacokinetic studies due to its emergence as a novel recreational substance. Absorption occurs rapidly via intranasal or intravenous routes, with effects onsetting within minutes, consistent with the high and rapid distribution of structurally related compounds like . Oral absorption is limited by extensive first-pass hepatic , yielding an estimated of 10-20%, analogous to 's reported 17% oral . Distribution is extensive, favoring lipophilic tissues including the , facilitated by its structure; however, ortho-fluorination on the phenyl ring may result in a higher unbound fraction compared to , potentially enhancing brain penetration despite slightly reduced overall lipophilicity. Metabolism is predominantly hepatic, mediated by enzymes such as and , which catalyze N-demethylation to norfluorexetamine and subsequent or other phase I modifications, producing fluorinated metabolites detectable in biological fluids. Halogen substitution, including , influences these pathways by modulating enzyme-substrate interactions, often decreasing clearance rates relative to non-fluorinated analogs. Elimination follows a pattern similar to , with a terminal estimated longer than ketamine's 2-4 hours, attributed to fluorination-induced reductions in metabolic clearance and prolonged systemic exposure. Primary excretion occurs renally, with approximately 90% of dose eliminated as metabolites in over 24-48 hours, as evidenced by postmortem toxicological detections of the parent compound and inferred metabolites in cases involving fluorexetamine.

Effects and Usage

Subjective and Physiological Effects

Fluorexetamine induces subjective effects typical of , including profound dissociation from the body and environment, analgesia, and perceptual alterations resembling those of . User reports describe immersion in cognitive activities, enhanced music , visual distortions, and a sense of liberated movement, often with a more stimulating profile than , featuring reduced and mild . Hallucinations, both internal (conceptual rethinking of personal experiences) and external, are frequently noted, alongside that prompts analysis of uncomfortable memories without inherent endorsement of therapeutic value. Physiological responses mirror those of related dissociatives like analogs, encompassing elevated , , and psychomotor activation such as increased locomotion. Agitation, abnormal behavior, and potential manic-like states have been documented in exposure cases, though specific incidences for fluorexetamine remain sparse and derived from limited clinical observations. Effects duration varies by route, purity, and individual factors, with anecdotal accounts indicating onset within minutes to an hour and persistence for 2–4 hours or longer in some instances. These reports, primarily from unregulated user communities, highlight variability and underscore the challenges in verifying purity, as analyses have revealed frequent adulteration in marketed samples.

Dosage and Administration

Due to the novel status of fluorexetamine (FXE) as a with limited clinical data, dosing lacks standardization and relies primarily on anecdotal reports from recreational users on online forums. Common doses range from 20 mg for threshold effects to 40-60 mg for moderate experiences comparable to low-dose use in social settings, with onset within 5-15 minutes and duration of 1-2 hours. typically requires higher amounts, around 50-100 mg for noticeable effects, though is lower than , leading to delayed onset (30-60 minutes) and extended duration (2-4 hours); (boofing) at 80-100 mg has been reported to produce rapid, intense "holing" similar to high-dose . The fluorine substitution on the phenyl ring may confer slightly enhanced potency relative to analogs, necessitating dose adjustments downward from equivalents to avoid over-intoxication, though direct comparisons vary by individual and purity of sourced material. Intravenous or is rarely reported due to risks of rapid onset and potential for overdose, but when attempted, doses are scaled even lower (10-30 mg) with immediate effects. Tolerance from prior use of like can significantly influence effective dosing, often requiring 20-50% increases for equivalent effects in experienced users, while cross-tolerance with other arylcyclohexylamines amplifies this variability. Harm reduction practices emphasize starting with low doses (e.g., 10-20 mg insufflated), volumetric dosing for accuracy, and avoiding redosing within the same session to mitigate accumulation and adverse outcomes.

Risks and Adverse Effects

Acute Toxicity and Overdose

Acute overdose of fluorexetamine (, 2-FDCK) primarily manifests through exaggerated and effects, including severe confusion, agitation, combativeness, , hallucinations, and loss or impairment of consciousness. Cardiovascular instability, such as and , alongside and , has been documented in intoxication cases, often compounded by co-ingestion of other substances like opioids, stimulants, or additional . Respiratory depression and seizures, inferred from structural analogs like , contribute to life-threatening outcomes, though direct empirical data on fluorexetamine's LD50 or dose-response thresholds in humans or animals are absent due to insufficient preclinical studies. Fatalities linked to fluorexetamine have been reported since at least 2021, predominantly in polydrug scenarios that exacerbate toxicity. In France, two forensic deaths and one self-mutilation case were attributed to 2-FDCK consumption, with postmortem analysis revealing the parent compound and metabolites like deschloroketamine (DCK) in blood at concentrations of 8–350 μg/L, alongside co-detected substances in some instances. A separate case involved a 42-year-old male found dead with fluorexetamine and 3-methoxyphencyclidine (3-MeO-PCE), where death was classified as non-specific asphyxia of toxic origin, highlighting synergistic risks with arylcyclohexylamine derivatives. Isolated fluorexetamine intoxication has been causally implicated in fatalities, such as one in Finland where it was the sole substance detected postmortem, underscoring potential for independent lethality at high doses. Over 60 confirmed intoxication cases, including hospitalizations, have been recorded in since 2019, frequently involving co-use and presenting with , cardiovascular, and digestive symptoms leading to overdose. An additional U.S. fatal overdose in was confirmed via testing, reflecting emerging detection in recreational markets. Forensic challenges arise from the compound's structural similarity to , resulting in initial misidentifications and underreporting; advanced analytical methods, such as LC-MS/MS, are required for accurate postmortem quantification, with blood concentrations in fatalities ranging variably but often exceeding therapeutic analog levels. No specific therapeutic interventions for fluorexetamine overdose are established, relying on supportive care analogous to ketamine management, including airway protection and benzodiazepines for agitation or seizures.

Long-Term Health Impacts

Due to the novelty of fluorexetamine (2-FDCK), a fluorinated analog of , empirical data on its long-term health impacts remain exceedingly limited, with no large-scale human cohort studies available as of 2025. As a non-competitive akin to , however, chronic exposure is presumed to carry analogous risks, including cognitive deficits extrapolated from class . Long-term recreational use has been associated with reductions in gray matter volume, diminished integrity, and impairments in and executive function, potentially arising from disrupted signaling and . These effects may persist post-abstinence, with evidence indicating altered thalamocortical connectivity in heavy users. Neurotoxicity concerns stem from repeated NMDA blockade, which in models induces Olney's lesions—vacuolar degeneration in posterior cingulate and retrosplenial cortices—following high-dose, sustained administration of . , despite similar mechanisms, has not reproducibly caused such lesions in humans at therapeutic or recreational doses, though preclinical data suggest dose-dependent vulnerability to excitotoxic damage via hyperactivation of non-NMDA receptors. For fluorexetamine, whose mirror ketamine's but with potentially higher potency, analogous cortical cannot be ruled out in chronic heavy users, particularly given its structural similarity and reports of prolonged states. Urological complications represent another extrapolated risk, paralleling ketamine-induced ulcerative cystitis observed in chronic abusers, characterized by detrusor overactivity, reduced capacity, and from direct toxic metabolites. In rat models, the dissociative analog provoked bladder inflammation and dysfunction after repeated dosing, implicating arylcyclohexylamine metabolites in epithelial damage. Anecdotal fluorexetamine reports describe urinary urgency and frequency akin to early cystitis, though confirmatory is absent; cessation may mitigate progression, but irreversible has occurred in cases exceeding 5 grams weekly for years. Psychiatric sequelae, including persistent perceptual disturbances or hallucinosis, have been documented in long-term users, potentially via enduring NMDA hypofunction mimicking schizophrenia-like syndromes. Fluorexetamine's sparse case data similarly hint at " holes"—gaps in —but lack controlled validation, underscoring the need for caution given the substance's recency and underreporting in clinical literature. Overall, while 's established profile informs these projections, fluorexetamine's unstudied metabolic profile and variable purity in illicit markets amplify uncertainty.

Dependence and Withdrawal

Fluorexetamine, as an structurally related to , exhibits a dependence potential characterized primarily by psychological rather than strong physical , akin to other arylcyclohexylamines. Preclinical studies demonstrate that it supports self-administration and drug-seeking behaviors in animal models, indicating reinforcing properties comparable to , which drives compulsive use through and analgesia. Clinical admissions for dependence have been documented, though underreported due to its status as a novel psychoactive substance. Tolerance develops rapidly with repeated use, necessitating higher doses to achieve similar effects, a pattern observed in chronic NMDA antagonist users and supported by fluorexetamine's pharmacokinetic profile favoring accumulation in lipid-rich tissues. This tolerance is psychological in nature, stemming from adaptations in signaling, with less emphasis on opioid-like . Cross-tolerance occurs with other arylcyclohexylamines such as and , complicating cessation as prior exposure to these substances may reduce fluorexetamine's efficacy and exacerbate cravings during abstinence. Withdrawal from fluorexetamine is generally milder than that of classic stimulants or opioids, manifesting as predominantly psychological symptoms including anxiety, depression, , , and intense cravings, based on analogies to discontinuation where such effects peak within 24-72 hours and subside over 1-2 weeks. Physical symptoms, if present, are subtle—such as mild tremors or sweating—and lack the severity of autonomic hyperactivity seen in alcohol or withdrawal, reflecting the drug's non-GABAergic mechanism. User reports highlight underreporting of protracted symptoms like persisting beyond acute phases, potentially due to limited epidemiological data on this .

Classification and Control Measures

Fluorexetamine is not explicitly scheduled under the U.S. at the federal level as of October 2025, distinguishing it from , which is classified as a Schedule III substance. Its structural resemblance to Schedule I and II arylcyclohexylamines, including (PCP), positions it for potential prosecution under the (21 U.S.C. § 813) if distributed or possessed with intent for human consumption, as the Act treats substantially similar chemical analogs of listed controlled substances as equivalents for enforcement purposes. This applicability hinges on demonstrating substantial similarity in chemical structure and pharmacological effects, though enforcement remains inconsistent due to interpretive challenges in and the need for intent-based determinations. At the international level, the Office on Drugs and Crime (UNODC) categorizes fluorexetamine as a phencyclidine-type new psychoactive substance (NPS), reflecting its emergence in global monitoring databases since detections around 2022. This classification underscores its alignment with anesthetics but highlights regulatory gaps, as NPS like fluorexetamine evade immediate scheduling through minor structural modifications that produce variants faster than legislative responses can adapt. State-level controls in the U.S. have begun addressing such analogs post-2022 forensic identifications, with some jurisdictions incorporating broad NPS bans or analog provisions into analog statutes, though comprehensive federal emergency scheduling has not occurred, exacerbating enforcement disparities across regions.

International Variations

Fluorexetamine's regulatory treatment exhibits significant international discrepancies, stemming from disparate national strategies toward novel psychoactive substances, ranging from outright prohibitions to precautionary surveillance. Within the , the substance is tracked via the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) , following formal notifications and confirmed detections in at least six member states by 2022. It lacks binding controls at the supranational level, fostering variations where certain countries invoke analogue bans on arylcyclohexylamines akin to , while others permit limited industrial or research handling absent explicit scheduling. The enforces a blanket prohibition under the , criminalizing production, supply, and related activities for unexempted NPS like Fluorexetamine detected in the early 2020s. In , analogous broad NPS provisions administered by the National Narcotics Control Commission encompass dissociatives such as Fluorexetamine, aligning with expansive listings implemented since the early 2020s to curb synthetic drug proliferation in . Global coordination through bodies like the (INCB) promotes harmonized vigilance on NPS trafficking, indirectly strengthening export and import restrictions via national implementations and information-sharing, though Fluorexetamine itself evades international scheduling under UN conventions.

History and Development

Emergence as a Novel Psychoactive Substance

Fluorexetamine emerged as a psychoactive substance in late 2022, with the first documented detection occurring in samples collected in October 2022. for Forensic Science Research and Education (CFSRE) issued a on December 16, 2022, identifying it as a analog structurally related to , based on initial case reports from routine drug testing. This marked its entry into monitored NPS surveillance systems, preceding broader clinical or epidemiological data. Online availability followed closely, with fluorexetamine appearing as a from vendors on clearnet and markets, marketed to users seeking ketamine-like effects. The European Monitoring Centre for Drugs and Drug Addiction's received formal notification of its presence in December 2022, citing seizures and user reports from research chemical suppliers. Its rise accelerated through user forums, where it was abbreviated as "FXE" and discussed extensively on subreddits dedicated to and . Mentions of FXE surged in November 2022, ranking as the second most discussed novel drug term behind fentanyl analogs, driven by anecdotal reports of potency and availability despite limited safety information. This forum-driven dissemination outpaced formal toxicological characterization, reflecting patterns seen in other rapidly proliferating NPS.

Market Availability and Detection

Fluorexetamine has been available for purchase primarily as a white powder or crystalline solid since at least 2017, with vendors offering quantities in gram-scale amounts marketed for purposes. Sales have occurred on markets at prices of $50–$80 per gram, though products are frequently impure or misrepresented, including misidentification with positional isomers like 2-fluoro-2-oxo-PCE in user-submitted samples analyzed prior to 2023. identifications have increased since 2023, with fluorexetamine noted as a novel psychoactive substance in seizures, such as in during that period. Analytical detection of fluorexetamine relies on liquid chromatography-mass spectrometry techniques, particularly LC-QTOF-MS for structural confirmation by matching mass spectral data against reference materials. By 2023, deuterated internal standards like fluorexetamine-d5 hydrochloride (≥99% deuterated forms) became commercially accessible, facilitating accurate quantification in biological and seized samples via LC-MS or GC-MS with improved precision over non-isotopically labeled methods. These advancements have supported routine forensic screening amid rising detections in novel psychoactive substance casework.

Society and Culture

Recreational Use Patterns

Fluorexetamine (2-FDCK) is predominantly consumed recreationally by experienced users of substances, particularly those familiar with , who seek analogues offering comparable and effects amid increasing regulatory scrutiny of traditional options. This niche appeal stems from its emergence around 2017 as a alternative, with documented human use remaining sparse and confined largely to online communities of and enthusiasts. Overall prevalence is low, reflected in fewer than two dozen detailed trip reports archived as of 2023, underscoring its status as a marginal novel psychoactive substance rather than a widespread recreational . Administration typically occurs via oral or intranasal routes, with users reporting effective doses of 25-70 mg orally yielding dissociation, analgesia, and mild lasting 2.5-5 hours. Anecdotal accounts highlight preferences for its subjectively more stimulating onset and reduced sedation relative to , facilitating easier integration into exploratory or social contexts without pronounced motor impairment at moderate doses. Polydrug use is common, often involving combinations with other , stimulants, or as an adulterant in mixtures like "" (a polydrug mimicking ), though such practices vary by individual experimentation. While specific or settings are not extensively reported for fluorexetamine, its ketamine-mimetic profile aligns with use in electronic music events or small-group sessions, where users leverage its potency for immersive experiences. Detection in drug-checking samples from public events further indicates occasional deployment as a ketamine substitute in dynamic social environments.

Public Health Concerns and Controversies

Fluorexetamine's status as an unscheduled novel psychoactive substance has prompted concerns over its potential for unpredictable adverse effects, including and severe dissociation reported in user accounts monitored by the National Drug Early Warning System (NDEWS). Online mentions of the drug surged beginning in summer 2021, reaching a peak in December 2022, with commenters attributing manic episodes to substances labeled as FXE, often consumed without knowledge of purity or dosage accuracy. These reports highlight the risks of self-administration in unregulated settings, where co-ingestion with other substances—common among users—amplifies toxicity, mirroring patterns observed with analogs but without clinical dosing guidelines. Forensic data links novel arylcyclohexylamines like fluorexetamine to intoxications and fatalities, though specific FXE-attributed deaths remain sparsely documented due to its recency and analytical challenges in postmortem testing. The Center for Forensic Science Research and Education (CFSRE) classifies FXE as a with effects akin to and , noting associations with life-threatening outcomes such as , seizures, and in the broader class. Unlike medically supervised , which benefits from established and lower impurity risks, FXE's illicit production fosters variability in potency, contributing to elevated harm potential in emergency contexts; NDEWS surveillance underscores this through rising detection in non-fatal poisonings involving from 2019 onward. Debates over NPS regulation intensify with fluorexetamine, as its rapid online dissemination—despite structural similarities to controlled —exposes gaps in scheduling mechanisms that allow proliferation before empirical risk data accumulates. Proponents of expedited controls cite Indonesia's 2023 identification of FXE in seizures as evidence that delays enable , potentially increasing overdose incidences absent proactive bans. Conversely, critics contend that overbroad prohibitions stifle pharmacological research into analogs' therapeutic potential, as seen with ketamine's applications, while driving production underground where adulteration heightens real-world toxicity beyond what controlled studies predict. This tension reflects broader causal realities: illicit markets inherently undermine by obscuring agent-specific risks, yet empirical comparisons reveal ketamine's regulated medical use yields far fewer severe outcomes than its street counterparts, suggesting FXE's dangers stem more from environmental uncontrollability than inherent molecular differences.

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