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2-Oxo-PCE
2-Oxo-PCE
2-Oxo-PCE
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2-Oxo-PCE
Legal status
Legal status
  • CA: Schedule I[1]
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • Illegal in Hong Kong[2] and Sweden[3]
Identifiers
  • 2-(ethylamino)-2-phenyl-cyclohexanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC14H19NO
Molar mass217.312 g·mol−1
3D model (JSmol)
  • CCNC1(CCCCC1=O)C2=CC=CC=C2
  • InChI=1S/C14H19NO/c1-2-15-14(11-7-6-10-13(14)16)12-8-4-3-5-9-12/h3-5,8-9,15H,2,6-7,10-11H2,1H3
  • Key:IDLSBAANXISGEI-UHFFFAOYSA-N

2-Oxo-PCE (also known as N-ethyldeschloroketamine, eticyclidone and O-PCE) is a dissociative anesthetic of the arylcyclohexylamine class that is closely related to deschloroketamine and eticyclidine, and has been sold online as a designer drug.[4][5][6][7][8][9][10][11]

See also

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References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

2-Oxo-PCE

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from Grokipedia

2-Oxo-PCE, also known as 2'-oxo-PCE, N-ethyldeschloroketamine, or eticyclidone, is a synthetic belonging to the class of novel psychoactive substances, structurally related to and eticyclidine through the absence of a substituent. It has emerged as a sold online for recreational use, producing effects akin to including dissociation, analgesia, and hallucinations, but with reports indicating potentially greater potency and toxicity. Notable incidents include clusters of acute poisonings characterized by impaired , convulsions, and , often more severe than those from , as well as its detection in cases, including a fatal overdose involving co-ingestion with . While lacking formal medical approval, its metabolism and detection have been studied in analytical contexts to address its illicit distribution, sometimes misrepresented as in street samples.

Chemistry

Structure and nomenclature

2-Oxo-PCE, also known as 2'-oxo-PCE or eticyclidone, is a synthetic compound belonging to the class. Its molecular formula is C₁₄H₁₉NO, with a molecular weight of 217.31 g/mol. The core structure consists of a ring, featuring a group at position 1 and both a phenyl and an ethylamino group (-NHCH₂CH₃) attached to the adjacent carbon at position 2, rendering it a 2,2-disubstituted . The systematic IUPAC name for 2-Oxo-PCE is 2-(ethylamino)-2-phenylcyclohexan-1-one. This nomenclature reflects the cyclohexanone parent chain, with the ethylamino and phenyl groups specified at the 2-position, prioritizing the amino substituent in naming convention. Common synonyms include N-ethyldeschloroketamine, highlighting its relation to ketamine analogs lacking the chlorine atom on the phenyl ring, and O-PCE, where "O" denotes the oxo (ketone) functionality distinguishing it from non-ketone arylcyclohexylamines like phencyclidine (PCP) or PCE. The compound's structure positions it as a deschloro variant of N-ethylketamine, contributing to its classification as a novel arylcyclohexylamine derivative.

Physical and chemical properties

2-Oxo-PCE, systematically named 2-(ethylamino)-2-phenylcyclohexan-1-one, possesses the molecular formula C14H19NO and a molecular weight of 217.31 g/mol. This derivative features a core with substitution at the alpha position by a phenyl ring and an ethylamino group, contributing to its chemical stability under neutral conditions but susceptibility to or oxidation in harsh environments. The secondary functionality enables and formation of water-soluble salts, such as the , which is the predominant form in illicit samples. In seized materials, 2-Oxo-PCE typically presents as a white to off-white powdery or crystalline solid, often visually indistinguishable from . Experimental data on key physical constants, including , , and profiles, remain sparsely documented in peer-reviewed sources, reflecting limited accredited characterization due to its emergence as a rather than a pharmaceutical entity. Computed physicochemical descriptors, such as (logP), suggest moderate hydrophobicity consistent with analogs, facilitating membrane permeation relevant to its pharmacological action, though exact values require further validation.

Synthesis

Laboratory synthesis

The laboratory synthesis of 2-Oxo-PCE, systematically named 2-(ethylamino)-2-phenylcyclohexan-1-one, follows routes established for α-aminoketones in the class, typically involving multi-step organic transformations starting from and phenyl-derived reagents. A foundational method, reported in 1966, utilizes thermal rearrangement of alicyclic α-hydroxyimines to generate 2-alkylamino-2-phenylcyclohexanones, including the N-ethyl variant. This approach begins with the preparation of 1-phenylcyclohexan-1-ol via Grignard addition of to , followed by conversion of the tertiary alcohol to an N-ethyl-substituted hydroxyimine intermediate, often through reaction with and an to form the requisite oxide or . Upon heating, generally in a high-boiling under conditions for several hours, the intermediate undergoes semipinacol-type rearrangement, wherein a carbon-carbon bond migrates, yielding the geminal ethylamino-phenyl substitution at the α-position relative to the reformed carbonyl. Yields in this rearrangement step typically range from 50-70% for analogous alkyl derivatives, with purification achieved via acid-base extraction and recrystallization as the salt. The method's selectivity arises from the stereoelectronic control in the rearrangement, favoring the desired α-aminoketone over elimination byproducts. Subsequent optimizations, including microwave-assisted or solvent-free conditions, have enhanced efficiency for related analogs, reducing reaction times from hours to minutes while maintaining comparable stereochemical outcomes, though specific adaptations for the N-ethyl phenyl compound remain sparse in peer-reviewed literature due to its niche status. These laboratory procedures require conditions, inert atmospheres, and standard glassware, underscoring the compound's synthesis as a controlled academic endeavor rather than scalable production.

Illicit production methods

Illicit production of 2-Oxo-PCE, also known as N-ethyldeschloroketamine, occurs primarily in clandestine laboratories, often in regions with limited regulatory oversight such as parts of and , where it is manufactured as a novel psychoactive substance (NPS) for online and street markets. The compound first appeared in forensic samples in in 2016, with subsequent detections in poisoning clusters across by 2018, indicating scaled-up illicit synthesis to meet demand for ketamine-like dissociatives. Synthesis routes for illicit 2-Oxo-PCE adapt laboratory methods developed for analogs like , the N-methyl variant first synthesized in the as a derivative but repurposed for recreational use. A typical multi-step process begins with the formation of an from and , followed by of a via organometallic reagents such as to the imine carbon, and subsequent to yield the 2-(ethylamino)-2-phenylcyclohexan-1-one structure. This approach mirrors the Grignard-mediated construction used in synthesis, where racemic mixtures are produced without , prioritizing yield over purity. Precursors like , ethylamine hydrochloride, and are commercially available and not strictly controlled, facilitating clandestine operations, though deviations from optimal conditions often introduce impurities such as unreduced imines or side-chain byproducts, contributing to variable potency and enhanced toxicity in seized samples. Forensic analyses of street products have identified 2-Oxo-PCE adulterated with opioids or other NPS, suggesting batch production in unregulated facilities lacking . Legal responses, including scheduling under the Misuse of Drugs Act as a Class B substance since 2016, have not halted production, as evidenced by ongoing detections in wastewater monitoring and seizures across and as of 2024.

Pharmacology

Pharmacodynamics

2-Oxo-PCE acts as a non-competitive antagonist at the , binding to the within the receptor's to block glutamate-induced calcium influx and excitatory neurotransmission in the and . This mechanism, shared with other derivatives like and , underlies its dissociative anesthetic properties, including analgesia, sedation, and disruption of thalamocortical communication. In vitro electrophysiological studies on rat hippocampal slices demonstrate that 2-Oxo-PCE potently and selectively inhibits NMDA receptor-mediated synaptic transmission and , exhibiting fast-onset blockade comparable to . While specific binding affinities (e.g., Ki or values) for 2-Oxo-PCE remain unreported in peer-reviewed literature, its structural similarity to suggests high-affinity interaction at the PCP site, contributing to pronounced and hallucinogenic effects observed in intoxication cases. Secondary interactions with other systems, such as release in mesolimbic pathways, may enhance reinforcing properties, though these are less characterized for this compound.

Pharmacokinetics

Limited pharmacokinetic data exist for 2-oxo-PCE, primarily derived from rodent studies and experiments using liver microsomes, reflecting its status as a novel dissociative with minimal clinical investigation. In rats administered 2-oxo-PCE orally at doses of 1.0–2.0 mg/kg, absorption is rapid, with peak blood concentrations achieved approximately 30 minutes post-administration via intragastric route. The compound distributes widely, showing highest tissue concentrations in the liver, alongside detection in blood and urine. Metabolism occurs primarily in the liver via phase I processes, including N-deethylation, carbonyl hydrogenation of the moiety, , oxidation to ketones, and , followed by phase II . rat studies identified four phase I metabolites and one glucuronidated phase II metabolite in urine, while incubation with pooled human liver microsomes confirmed 19 phase I metabolites, underscoring hepatic P450-mediated akin to other arylcyclohexylamines. No human-specific pharmacokinetic parameters, such as or clearance, have been reported. Excretion is predominantly renal, with conjugated metabolites exhibiting the highest urinary response intensities in rats; parent compound and metabolites remain detectable in urine for analytical purposes using LC-HRMS/MS, with limits of identification around 10 µg/L.

History

Early development ()

2-Oxo-PCE, chemically known as 2-(ethylamino)-2-phenylcyclohexan-1-one or N-ethyldeschloroketamine, was first synthesized in 1962 during pharmaceutical research efforts to create shorter-acting analogs of (PCP), a initially developed by in the mid-1950s. This work occurred concurrently with the synthesis of by Calvin L. Stevens at the same institution, as part of broader exploration of derivatives for applications. The compound represented an early attempt to modify PCP's structure—replacing the ring with an ethylamino group and incorporating a at the 2-position on the cyclohexane ring—to reduce duration of action and potentially mitigate side effects like prolonged observed with PCP. However, unlike , which advanced to human trials by 1964 and gained FDA approval in 1970 for use as a general , 2-oxo-PCE showed limited promise in preliminary evaluations and was not pursued for clinical development during the . Alongside eticyclidine (PCE), another PCP analog synthesized around the same period, 2-oxo-PCE exemplified the era's focus on structural variations of arylcyclohexylamines to optimize dissociative properties for medical use, though neither PCE nor its 2-oxo variant achieved the success of . No documented animal or human pharmacological studies specific to 2-oxo-PCE from this decade have been reported, indicating it remained largely an experimental synthesis without further advancement.

Emergence as a novel psychoactive substance (2010s–present)

2-Oxo-PCE, chemically known as 2-(ethylamino)-2-phenylcyclohexan-1-one, re-emerged in the mid- as a novel psychoactive substance within the class, marketed online as a analog of lacking the . Although originally synthesized in 1962 during efforts to develop short-acting derivatives, it saw no significant clinical or recreational use until vendors began distributing it to evade regulations. The compound's first documented detection in the illicit market occurred in in 2016, coinciding with the broader proliferation of deschlorinated analogs amid tightening controls on established dissociatives. By late 2017, 2-Oxo-PCE had surfaced prominently in , with authorities reporting its initial identification in 31 drug seizure cases involving 52 items and 4 drug-impaired driving incidents starting in October 2017. This was rapidly followed by a cluster of 56 acute intoxication episodes over two months, characterized by symptoms including impaired (84% of cases), (60%), and agitation (50%), prompting alerts. The substance's availability through online vendors facilitated its spread, often misrepresented or adulterated with other ketamine-like compounds, contributing to its appeal among users seeking dissociative effects similar to those of controlled arylcyclohexylamines. In the ensuing years, 2-Oxo-PCE has persisted in global NPS monitoring, with detections in analyses linked to overdoses and fatalities, such as a case involving co-ingestion with where postmortem concentrations reached 1.2 μg/mL in blood. European and North American forensic reports from 2018 onward highlight its role in poly-substance intoxications, while analogs like 2-fluoro derivatives emerged by 2022, underscoring ongoing structural modifications to sustain market presence. Regulatory responses, including scheduling under Germany's New Psychoactive Substances Act in 2019, reflect its established risks, yet underground production and online sales continue to drive sporadic outbreaks.

Effects and usage

Subjective effects from user reports

User reports indicate that 2-Oxo-PCE, also known as O-PCE or eticyclidone, produces effects akin to those of or (MXE) but with greater potency, stimulation, and duration, often lasting 8-12 hours or longer at higher doses. Common physical sensations include initial warmth, tingling, and numbness, progressing to heavy sedation and body dissociation, with impaired coordination such as difficulty walking reported at moderate doses around 5 mg insufflated. Cognitively, the experience features minimal suppression in the early phase, characterized by stimulation and energy, followed by pronounced dissociation in the latter half, sometimes described as chaotic or entheogenic with memory disruptions resembling a "reboot." Visual effects are typically mild to moderate, including distorted perceptions (e.g., altered hand size or wobbly vision), closed-eye colorful shapes or faces, and open-eye tracers or green-tinged distortions at cumulative high doses exceeding 50 mg rectally. Emotionally, users report initial euphoria and bounciness at low doses (1-5 mg), shifting to contemplative solemnity, spiritual connection, or mood elevation persisting into the next day, though lacking the pronounced physical warmth of MXE. Higher doses are likened to phencyclidine (PCP) in heaviness, promoting calm introspection over recreational partying, with onset varying by route: 15-45 minutes rectally or insufflated. Adverse subjective elements include nausea, headaches, and overstimulation leading to unpredictable responses.

Clinical and pharmacological effects

2-Oxo-PCE, also known as eticyclidone or deschloro-N-ethyl-ketamine, exerts its primary pharmacological effects through non-competitive antagonism of N-methyl-D-aspartate (NMDA) receptors, a mechanism shared with prototypical arylcyclohexylamines such as and . This blockade inhibits glutamate-mediated excitatory , resulting in dissociative characterized by sensory detachment, analgesia, and psychotomimetic states. Unlike , which includes a chlorine enhancing receptor affinity, the deschlorinated of 2-Oxo-PCE may alter binding kinetics, though specific affinity constants (e.g., Ki values) remain unreported in peer-reviewed literature due to limited preclinical characterization. Clinical data on 2-Oxo-PCE is absent from controlled human trials, as it lacks regulatory approval for medical use and has emerged solely as a novel psychoactive substance. Observations derive exclusively from and clusters, where intravenous or produced ketamine-like effects but with heightened severity, including impaired consciousness in 84% of cases, confusion in 60%, and agitation in 56%. These manifestations suggest a narrower compared to , with elevated risks of cardiovascular stimulation (e.g., ) and neurological excitation (e.g., convulsions), potentially attributable to differential NMDA subtype selectivity or off-target interactions not yet delineated. In metabolic studies using models, 2-Oxo-PCE undergoes phase I transformations including hydrogenation, N-deethylation, and , yielding detectable urinary metabolites that inform its and elimination profile, though human await confirmation. No evidence supports or neuroprotective applications akin to , and its pharmacological profile underscores recreational rather than therapeutic utility.

Adverse effects and toxicity

Acute adverse reactions

Acute adverse reactions to 2-oxo-PCE, a analogue of , have been documented primarily through a 2018 cluster of 25 acute poisoning cases in , where the substance was misrepresented as . In cases attributed to sole 2-oxo-PCE ingestion, the most prevalent symptoms included impaired consciousness in 84% of patients, confusion in 60%, and abnormal behavior in 44%. was observed in 80% of affected individuals, alongside and agitation. Other reported manifestations encompassed aggressive behavior, loss of balance, and hallucinations, often requiring hospitalization for supportive care such as and monitoring. These reactions typically onset rapidly after oral or intranasal administration, with even low doses (e.g., 35-40 mg) linked to pronounced disorientation and , distinguishing 2-oxo-PCE from due to its higher potency at NMDA receptors and potentially greater risk of . Clinical focuses on airway , benzodiazepines for agitation, and cardiovascular stabilization, as no specific exists. Limited pharmacological data suggest these effects stem from uncompetitive NMDA antagonism, leading to dysregulation and sympathomimetic stimulation, though human trials are absent and reports rely on observations. Subsequent outbreaks, including a 2020 cluster involving related fluoro analogues, reinforce patterns of acute neuropsychiatric and autonomic .

Overdose cases and fatalities

A single fatal intoxication involving 2-oxo-PCE has been documented in the , concerning a 52-year-old man found deceased in his bedroom in 2018, with postmortem confirming the presence of N-ethyldeschloroketamine (2-oxo-PCE) alongside , an . The case highlighted potential cardiotoxic and neurotoxic effects, though the exact contribution of 2-oxo-PCE versus remains undetermined due to the combined substances. Systematic reviews of ketamine analogue overdoses report 56 acute poisoning cases linked to 2-oxo-PCE, representing 18% of non-ketamine dissociative overdoses in the analyzed dataset from primarily European poison control centers between 2010 and 2020. These incidents frequently involved severe symptoms exceeding those typical of ketamine, including higher rates of impaired consciousness (observed in over 50% of cases), convulsions, and hypertension, suggesting greater toxicity potential. No standalone fatalities were identified beyond the poly-drug case, though underreporting is possible given the substance's emergence as a novel psychoactive and its misrepresentation in illicit markets.

Long-term risks and dependence potential

Limited empirical data exist on the long-term risks of 2-Oxo-PCE due to its emergence as a novel psychoactive substance primarily in the , with most research focusing on rather than chronic exposure. As an derivative structurally related to , it may theoretically share risks such as persistent cognitive deficits, including memory impairment and , which have been documented in long-term users through and neuropsychological studies; however, no peer-reviewed investigations confirm these effects specifically for 2-Oxo-PCE. Urinary tract complications, akin to ketamine-induced cystitis involving and , remain unexamined for this analog, underscoring the gap in causal data. Dependence potential mirrors that of other dissociative anesthetics in its class, characterized by rapid tolerance development upon repeated administration, necessitating escalating doses to achieve comparable effects. , including cravings and compulsive use patterns, has been frequently reported among users, driven by reinforcement of and euphoric states via antagonism. Physical withdrawal symptoms appear minimal compared to opioids or stimulants, but psychic reliance can perpetuate cycles of misuse, as evidenced in clinical observations of similar compounds. United Nations Office on Drugs and Crime assessments of new psychoactive substances, including 2-Oxo-PCE, highlight limited but emerging evidence of liability, though prospective studies are needed to quantify incidence rates.

International and national regulations

2-Oxo-PCE is not subject to international control under the or other global treaties, as it does not appear on the INCB's Green List of scheduled substances. In the United States, 2-Oxo-PCE is not explicitly listed in the federal schedules of the , allowing its possession and distribution in unregulated contexts unless prosecuted as a to under the when intended for human consumption. State-level controls vary, with no uniform scheduling reported as of 2024. In , 2-Oxo-PCE is monitored as a new psychoactive substance but not explicitly scheduled under the , though related analogs fall under Schedule I provisions for dissociative anesthetics. classifies 2-Oxo-PCE as a controlled substance under its national narcotics regulations, with additions to prohibited lists including it among ketamine analogs targeted in updates through 2024. In the , 2-Oxo-PCE is prohibited as a psychoactive substance under the , criminalizing its production, supply, offer to supply, and possession with intent to supply, irrespective of specific scheduling under the Misuse of Drugs Act. Germany regulates 2-Oxo-PCE under the New Psychoactive Substances Act (NpSG) effective July 2019, restricting its manufacture, trade, and possession beyond industrial or scientific purposes. It is also banned in Sweden and Hong Kong, where it is explicitly listed among prohibited narcotics or falls under broad controls on dissociative analogs. In other European Union countries, it is typically managed through national NPS frameworks or EU early warning systems via EMCDDA monitoring, leading to ad hoc bans.

Detection and societal impact

Analytical detection challenges

Detection of 2-oxo-PCE, a novel arylcyclohexylamine dissociative, in biological matrices and seized materials is complicated by its structural similarity to ketamine and other designer drugs, often requiring targeted analytical approaches beyond routine screening. Immunoassay-based tests, such as enzyme-linked immunosorbent assays (ELISA) for common substances of abuse, typically do not cross-react sufficiently with 2-oxo-PCE to enable reliable presumptive identification, as these assays lack antibodies specific to its deschloro-N-ethyl-ketamine structure. However, cross-reactivity has been observed in phencyclidine (PCP) immunoassays, resulting in false-positive PCP results that necessitate confirmatory testing to avoid misattribution in clinical or forensic contexts. Confirmatory detection relies on chromatographic techniques coupled with , including gas chromatography- (GC-MS) for volatile derivatives and liquid chromatography-tandem (LC-MS/MS) for polar metabolites in or . These methods exploit characteristic fragmentation patterns, such as loss of the ethylamino group or cyclohexyl ring cleavage, but demand validated reference standards and optimized extraction protocols, like dual-mode extraction, to achieve sufficient sensitivity (e.g., limits of detection around 1-10 ng/mL in ). For analogues like 2-fluoro-2-oxo-PCE, LC-MS/MS screening interferences have prompted secondary GC-MS verification in driving-under-influence cases, highlighting the risk of spectral overlap with co-eluting compounds. Further challenges arise from incomplete characterization of 2-oxo-PCE's metabolism, with primary phase I metabolites (e.g., N-desethyl-2-oxo-PCE) detectable in rat urine via high-resolution MS but varying in human detectability and stability. This limits retrospective detection windows, particularly in non-targeted workflows, and complicates quantification in postmortem samples where postmortem redistribution or degradation may occur. Biotransformation studies indicate potential microbial instability in wastewater or stored specimens, underscoring the need for prompt analysis and method validation tailored to arylcyclohexylamines. Isomeric variants, such as those encountered in fluorexetamine-related seizures, exacerbate identification errors even when mass-to-charge ratios match reporting criteria, often requiring orthogonal techniques like NMR for unambiguous structural elucidation in reference labs.

Misrepresentation in drug markets and public health implications

In illicit drug markets, 2'-oxo-PCE has been frequently misrepresented, with samples labeled or sold as other substances such as (DCK), , or , leading users to ingest it under false expectations of effects and potency. Additionally, laboratory analyses of products marketed as 2'-oxo-PCE have revealed adulteration with related compounds, including 2-fluoro-2-oxo-PCE, which alters the expected pharmacological profile and dosing assumptions. Such mislabeling exploits the rapid evolution of novel psychoactive substance (NPS) markets, where vendors substitute or blend analogues to evade detection or meet demand for established dissociatives like . This misrepresentation exacerbates risks by promoting unintended polydrug use and dosage errors; for instance, consumers anticipating effects from purported may escalate intake, resulting in profound dissociation, , or characteristic of arylcyclohexylamines. Clinical reports document clusters of acute poisonings linked to 2'-oxo-PCE, featuring ketamine-like symptoms but with elevated rates of severe outcomes such as impaired consciousness (observed in multiple cases), convulsions, and compared to itself. A documented fatality involved co-ingestion with , where 2'-oxo-PCE contributed to respiratory depression and cardiovascular collapse, underscoring its potential for lethal interactions when misrepresented or combined unexpectedly. Broader implications include heightened toxicity profiles relative to , with evidence of more severe dissociative states and motor impairment at equivalent doses, complicating efforts in unregulated markets. The proliferation of such NPS analogues strains systems through increased emergency presentations and forensic challenges, as users often lack awareness of batch variability or synergistic risks with stimulants and antidepressants prevalent in misrepresented products. Systematic monitoring, such as through services, reveals these discrepancies, yet market opacity perpetuates cycles of acute intoxications and long-term uncertainties regarding or dependence in unsuspecting populations.

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