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AMB-FUBINACA

AMB-FUBINACA (methyl 2-({1-[(4-fluorophenyl)methyl]-1H--3-carbonyl}amino)-3-methylbutanoate) is a synthetic carboxamide that functions as a potent of the CB₁ receptor, exhibiting far greater binding affinity and efficacy than Δ⁹-tetrahydrocannabinol. Originally synthesized in pharmaceutical contexts, it emerged on markets around 2014 as a component of ""-like herbal products designed to mimic intoxication while circumventing legal restrictions on natural . Its extreme potency—orders of magnitude higher than THC—has led to rapid onset of severe effects including profound sedation, impairment, seizures, cardiovascular instability, and respiratory , contributing to clusters of acute overdoses and fatalities reported internationally. In recognition of these risks, AMB-FUBINACA was designated a Schedule I under the U.S. , reflecting its high abuse potential and lack of accepted medical use. Pharmacological studies indicate primary metabolism via hepatic carboxylesterases to an active , with effects persisting 2–4 hours post-administration, though toxicity can manifest abruptly due to narrow therapeutic margins.

Chemical and Physical Properties

Molecular Structure and Formula

AMB-FUBINACA, systematically named methyl (2S)-2-{[1-[(4-fluorophenyl)methyl]-1H-indazole-3-carbonyl]amino}-3-methylbutanoate, possesses the molecular formula C_{21}H_{22}FN_3O_3 and a molecular weight of 383.42 g/mol. The compound contains a chiral center at the alpha carbon of the valinate moiety, with the naturally occurring (S)-configuration predominant in reported samples. The core structure consists of an indazole ring substituted at the N-1 position with a 4-fluorobenzyl group and at the C-3 position with a carboxamide linkage to the N-terminus of methyl L-valinate, forming -C(O)NH-CH(CH(CH_3)_2)-C(O)OCH_3. This indazole-3-carboxamide framework, distinct from the naphthoylindole cores of earlier synthetic cannabinoids such as JWH-018, enables potent CB1 receptor agonism while differing in binding interactions due to the heterocyclic nitrogen and fused ring system. Relative to the analog AB-FUBINACA, which substitutes the terminal methyl ester with a primary amide (-C(O)NH_2), AMB-FUBINACA's ester modification represents a subtle structural variation that alters lipophilicity and metabolic stability without changing the overall indazole scaffold. Such tweaks in peripheral groups have been employed to generate analogs evading initial bans targeting specific naphthoyl or adamantyl motifs in controlled substances schedules.

Synthesis and Precursors

The synthesis of AMB-FUBINACA (N-[[1-(4-fluorophenyl)methyl]indazole-3-carbonyl]-L-valine methyl ) follows a standard multi-step route common to indazole-3-carboxamide class , involving N-alkylation, , and amide bond formation. This process begins with the regioselective N1-alkylation of commercially available methyl 1H-indazole-3-carboxylate using 1-(bromomethyl)-4-fluorobenzene (4-fluorobenzyl bromide) as the alkylating agent, typically in (DMF) with (NaH) as base under atmosphere at 0°C to for 24 hours, yielding the intermediate 1-(4-fluorobenzyl)-1H-indazole-3-carboxylic acid methyl in approximately 81% yield. The ester group is then hydrolyzed to the corresponding by treatment with 1 M aqueous in at for 48 hours, affording 1-(4-fluorobenzyl)-1H-indazole-3- in near-quantitative yield (98%). This acid undergoes amide coupling with methyl 2-amino-3-methylbutanoate (derived from L-valine) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (·HCl) and 1-hydroxybenzotriazole hydrate (HOBt·H₂O) as coupling reagents, in the presence of triethylamine, at for 18 hours, producing AMB-FUBINACA with yields ranging from 29% to 99% depending on purification. Key precursors—methyl 1H--3-carboxylate, 4-fluorobenzyl bromide, and L-valine methyl ester—are readily available from chemical suppliers and have been used in forensic and pharmacological studies to prepare reference standards, though their accessibility has prompted regulatory scrutiny for potential clandestine production. This synthetic pathway, detailed in peer-reviewed literature, emphasizes at the indazole N1 position to avoid 2-alkyl isomers, which exhibit distinct pharmacological profiles. Variations may employ alternative bases or solvents, but the core sequence remains consistent across reported preparations.

Pharmacology

Receptor Interactions

AMB-FUBINACA demonstrates high binding affinity for the CB1 receptor, with reported values of approximately 1.9 nM in displacement assays. It acts as a full at CB1, exhibiting substantially greater efficacy than Δ9-THC in functional assays measuring receptor activation. studies indicate an 85-fold higher potency at CB1 compared to Δ9-THC, underscoring its enhanced agonism relative to the phytocannabinoid. Affinity for the CB2 receptor is lower, with values reported around 10 nM or less in human assays, though selectivity favors CB1-mediated effects due to tissue distribution and potency differences. At supratherapeutic concentrations exceeding 1 μM, AMB-FUBINACA can disrupt CB1 receptor signaling pathways in a concentration-dependent manner, potentially indicating non-orthosteric interactions or off-target modulation, though its primary mechanism involves the orthosteric binding site. Compared to structural analogs like ADB-FUBINACA, which shows up to 140-fold greater CB1 potency over Δ9-THC, AMB-FUBINACA exemplifies the progressive enhancement of agonistic strength in indazole-based synthetic cannabinoid receptor agonists (SCRAs), driven by amide chain modifications that optimize receptor engagement. This trend reflects iterative structural evolution prioritizing nanomolar CB1 affinity and full agonism for illicit potency.

Pharmacodynamics

AMB-FUBINACA functions as a full agonist at the cannabinoid receptor type 1 (CB1), a Gi/o-coupled receptor predominantly expressed in the central nervous system. Receptor activation recruits Gi/o proteins, which inhibit adenylyl cyclase activity, leading to decreased intracellular cyclic AMP (cAMP) levels and modulation of downstream effectors such as voltage-gated calcium channels and inwardly rectifying potassium channels. This signaling cascade presynaptically suppresses neurotransmitter release, including inhibition of GABA and glutamate, through reduced calcium influx and increased potassium conductance. Unlike partial agonists such as Δ9-tetrahydrocannabinol (THC), AMB-FUBINACA exhibits high without a signaling ceiling, enabling maximal receptor activation and potential over-stimulation of CB1-mediated pathways. At concentrations exceeding 1 μM, it induces concentration-dependent disruption of CB1 receptor signaling, possibly via biased agonism or off-target interactions that alter G-protein coupling . In vitro studies using neuronal models like NG108-15 cells demonstrate that AMB-FUBINACA exposure dysregulates peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC-1α), a key regulator of mitochondrial biogenesis, alongside reductions in mitochondrial membrane potential independent of CB1 activation. These effects suggest interference with cellular energy homeostasis and oxidative stress responses at the organelle level.

Pharmacokinetics and Metabolism

AMB-FUBINACA demonstrates rapid absorption following in models, achieving peak concentrations shortly after dosing. Pharmacokinetic parameters include a of 5.91 hours, a of 203.13 L, and clearance of 23.81 L/h, indicating efficient distribution and elimination. In vitro stability assessments show the compound remains largely intact in human , with approximately 86% of the original concentration preserved after five hours of incubation. Metabolism occurs primarily in the liver via phase I and II processes, with ester hydrolysis as a dominant pathway yielding a metabolite. Additional transformations include , particularly at the chain and ring, followed by in some cases, and phase II of hydroxylated and products, rendering metabolites detectable in for forensic . These pathways, observed in liver microsomes and in vivo models like zebrafish larvae, highlight rapid that contributes to the compound's short duration of action. Distribution is influenced by high binding affinity to (HSA), with AMB-FUBINACA exhibiting approximately 99% binding, primarily at Sudlow's site I. A 2025 study using spectroscopic and docking methods confirmed this extensive protein interaction, which may limit free plasma concentrations and affect tissue penetration. The short suggests low potential despite variable dosing in illicit preparations.

Effects and Toxicity

Psychoactive and Physiological Effects

AMB-FUBINACA produces psychoactive effects that partially mimic those of Δ⁹-tetrahydrocannabinol (THC), including , relaxation, and altered perception, though these are often overshadowed by due to its full agonism at CB₁ receptors, lacking the modulating of natural . In drug discrimination studies with rats, AMB-FUBINACA substitutes for THC, indicating overlapping subjective effects, but its higher potency—exceeding that of THC by factors observed in potency assays—intensifies outcomes, frequently leading to psychological distress such as severe , , hallucinations, , anxiety, and delusions rather than consistent recreational highs. Physiologically, acute exposure elevates heart rate (), blood pressure (), and body temperature (), consistent with CB₁-mediated sympathetic activation, alongside drowsiness and reported in case observations. These effects arise from potent overactivation of central and peripheral systems, contrasting with THC's milder partial agonism, and contribute to unintended harms even at low recreational doses. The compound's short duration of action, typically 1-2 hours based on pharmacokinetic profiles and user reports extrapolated from similar synthetic cannabinoids, encourages redosing and heightens risks of cumulative exposure, despite its brevity challenging assumptions of negligible dependence potential. In mice, the structurally analogous AB-FUBINACA induces with somatic withdrawal signs after repeated short exposures, suggesting that AMB-FUBINACA's rapid onset and offset do not preclude rapid via CB₁ downregulation.

Acute Toxicity and Overdose Symptoms

Acute toxicity from AMB-FUBINACA manifests primarily through and cardiovascular excitation, with reported symptoms including severe lethargy, , seizures, , , and loss of consciousness. Other physiological effects encompass , , , , , eye flushing, and impaired motor performance. These arise from potent CB1 receptor agonism, which exceeds that of delta-9-tetrahydrocannabinol (THC) by orders of magnitude, enabling microgram-level doses to produce effects mimicking milligrams of natural but with disproportionate excitatory and depressive risks. Overdose symptoms escalate to life-threatening conditions such as respiratory depression, , , and multi-organ failure, often compounded by co-ingestion of other substances or unknown product purity. Concentrations in laced materials have ranged from 14.2 to 58.5 mg per gram, facilitating inadvertent high dosing via or , as seen in outbreaks like the 2016 New York "zombie" incident where users experienced profound and required hospitalization. Non-fatal serum levels have been documented at 58.7–115.9 ng/mL, while fatalities involve similar or higher concentrations alongside metabolites, with death attributed to , , or encephalopathies rather than inherent metabolic toxicity alone. Risk amplification stems from variable potency and adulteration, where synergism with opioids or stimulants exacerbates and seizures, contrasting with the milder profile of natural and underscoring the hazards of unregulated synthetic formulations. Case reports highlight causality through toxicological confirmation, with postmortem analyses revealing AMB-FUBINACA as the primary agent in acute collapses, devoid of pre-existing conditions in many instances. Empirical data from peer-reviewed refute portrayals of equivalent safety to THC, as synthetic variants induce greater neuropsychiatric disruption and autonomic instability per unit dose.

Notable Incidents and Casualties

In July 2016, a mass event in , , affected 33 individuals who exhibited severe altered mental status, including catatonia and unresponsive states described as "zombie-like," after smoking synthetic cannabinoid-laced herbal products marketed as K2. analysis of patient urine and product samples confirmed AMB-FUBINACA as the causative agent, with its de-esterified metabolite detected in biological fluids despite no parent compound in blood. No fatalities were reported in this outbreak, but the incident highlighted the drug's potency, estimated at up to 85 times that of delta-9-tetrahydrocannabinol, leading to rapid onset of depressant effects. From late May 2017 to early 2019, an outbreak in , , resulted in 64 deaths linked to AMB-FUBINACA use, representing the highest recorded mortality associated with this synthetic cannabinoid receptor agonist during that period. Toxicological evidence from postmortem and in these cases confirmed the presence of AMB-FUBINACA or its metabolites, often in combination with other substances, with most victims being male and averaging 42 years of age. This cluster underscored the drug's role in events, prompting enhanced monitoring and contributing to 's peak in synthetic cannabinoid-related fatalities. In the United States, AMB-FUBINACA (also known as FUB-AMB) was implicated in multiple prison overdose deaths, particularly in , where between March 2017 and November 2018, analysis of 54 fatal cases from state correctional facilities detected the compound alongside other like and MDMB-FUBINACA. These incidents contributed to a spike in accidental deaths within prisons, rising from 12 in 2016 to 62 in 2017, with identified as a primary factor in the incarcerated population's vulnerability due to limited medical access and high-potency adulteration. Detections of AMB-FUBINACA have persisted into 2023–2025 through routine new psychoactive substance monitoring, including in clinical urine samples and wastewater analyses, but without reports of large-scale outbreaks or mass casualties comparable to earlier events. This ongoing presence reflects sustained illicit circulation, though regulatory scheduling has reduced acute intoxication clusters in monitored regions.

History and Production

Development and Early Research

AMB-FUBINACA was first documented as a derivative in international WO 2009/106980-A2, filed by researchers at and published on September 3, 2009, as part of a series of indazole-3-carboxamide compounds designed as potent for potential applications. This development built on prior synthetic research aimed at elucidating the endocannabinoid system's role in pain modulation, with the core selected for its structural mimicry of Δ9-tetrahydrocannabinol (THC) pharmacophores while enhancing receptor affinity. The compound, featuring a valinate linkage, was synthesized to probe structure-activity relationships at cannabinoid receptors CB1 and CB2, but did not pursue it beyond preclinical disclosure due to challenges in selectivity and safety profiles typical of high-potency agonists. Early pharmacological investigations, conducted primarily in academic and pharmaceutical laboratories before , confirmed AMB-FUBINACA's exceptional potency as a tool compound for receptor studies, with in vitro assays revealing a CB1 value of approximately 10 and functional up to 85-fold greater than THC in cAMP inhibition models. These experiments emphasized its role in modeling signaling pathways, including downstream effects on G-protein coupled receptor activation, without evidence of targeted therapeutic optimization or human trials. The absence of clinical intent reflected broader trends in synthetic research, where such derivatives served as non-patented probes to dissect THC-like amid regulatory constraints on natural analogs. Forensic laboratories first identified AMB-FUBINACA in seized materials in during late 2014, prompting initial analytical characterizations that corroborated its preclinical potency through and receptor binding validations. These detections highlighted the compound's evolution from a synthetic intermediate in exemplars to a reference standard for emerging , driven by academic interest in evading barriers while advancing causal understanding of CB1-mediated effects. Pre-2016 studies further quantified its selectivity, noting minimal CB2 affinity relative to CB1, underscoring its utility in isolating central nervous system-specific mechanisms over peripheral .

Emergence in Illicit Markets

AMB-FUBINACA first appeared in illicit markets around 2014 as a novel synthetic agonist (SCRA), capitalizing on regulatory gaps left by bans on prior compounds such as and AM-2201. Marketed as an alternative to "" or products, it was typically dissolved in solvents and sprayed onto dried plant material like damiana or marshmallow leaves, creating smokable herbal blends that mimicked high while evading standard drug tests. Its low production costs—stemming from straightforward using commercially available precursors—and potency made it attractive for vendors seeking profitable, legal-evasion substitutes for THC. Prevalence escalated between 2016 and 2018, particularly , where it predominated alongside analogs like ADB-FUBINACA in urban settings and correctional facilities. A notable early incident occurred on July 12, 2016, in , , when 33 individuals experienced acute intoxication from AMB-FUBINACA-laced "AK-47 24 Karat Gold" herbal incense, highlighting its rapid dissemination via street-level distribution networks. In prisons across the US, , and , it was commonly smuggled as infusions on correspondence paper, exploiting its detectability challenges and appeal to inmates barred from . User demographics skewed toward those pursuing euphoric effects without urinalysis flags, including young adults in high-drug-testing environments like or sectors. Following its temporary placement into Schedule I by the DEA in January 2017, direct market share declined as producers pivoted to non-controlled structural analogs with minor modifications to or chains. However, early warning systems reported sporadic detections of AMB-FUBINACA itself persisting into the early , with traces noted in via EMCDDA-monitored seizures and in forensic samples amid broader SCRA cycles. This pattern underscores adaptability, where vendor innovation in analog design sustained supply despite targeted bans, driven by ongoing demand for cheap, evasive intoxicants.

Sources of Production and Distribution

AMB-FUBINACA is primarily synthesized in clandestine laboratories, with serving as a major hub for production due to the availability of chemical and established manufacturing capabilities for . These , often initially unregulated, are used to produce the compound as a pure , which is then exported internationally for further processing. data from international agencies indicate that bulk shipments originate from Chinese suppliers, highlighting the role of Asian chemical industries in supplying high-purity formulations at scale. Distribution networks rely on the form being shipped via international mail or , often to , , and other regions, where it is dissolved in solvents and sprayed onto dried material to create smokable products mimicking herbal incense. This lacing process amplifies volume significantly; for instance, 1 kg of AMB-FUBINACA can be mixed with approximately 66 kg of inert herb to yield around 100,000 doses, facilitating low-cost, high-volume sales. Channels include marketplaces offering bulk or pre-laced products, as well as physical outlets like head shops marketing them as "legal highs" or variants, though enforcement has disrupted some vendors. Following China's 2021 generic ban on indazole- and indole-3-carboxamide synthetic cannabinoid classes, producers adapted by developing "tail-less" precursors—unsaturated analogs evading structural controls through one-step synthesis into controlled substances. These innovations, detected in grey market samples since late 2021, persisted into 2024 with variants incorporating novel side chains, maintaining supply despite regulatory pressures. Bulk production costs remain low, with pure powder available online for $1.95 to $3.80 per gram in quantities up to kilograms, enabling unregulated trade where inconsistent dosing on laced materials contributes to widespread variability in potency and associated risks.

United States Scheduling

The (DEA) temporarily scheduled AMB-FUBINACA, also known as FUB-AMB or MMB-FUBINACA, as a under the effective November 3, 2017. This action was justified by findings of its high abuse potential, absence of accepted medical use, and lack of safety for use under medical supervision, with evidence of pharmacological effects akin to delta-9-THC but exceeding it in potency and associated risks, including severe observed in intoxication cases. The scheduling followed analytical confirmation of AMB-FUBINACA in products linked to acute outbreaks, such as the July 12, 2016, incident in , , where 33 individuals exhibited "zombie-like" , catatonia, and respiratory after smoking synthetic cannabinoid-laced herbs, prompting rapid response and underscoring its role as a potent depressant up to 85 times stronger than THC at CB1 receptors. Prior to federal temporary controls, several states preemptively banned AMB-FUBINACA via emergency declarations after local detections in illicit products; for instance, Louisiana implemented such a prohibition through state health department rules in response to emerging synthetic cannabinoid threats, reflecting faster state-level agility amid rising hospitalizations. The DEA's rationale emphasized incident data, including prison and community overdoses tied to its distribution as "zombie drug" variants, which drove urgency for federal intervention to curb imminent public safety hazards. Permanent Schedule I placement was finalized on March 30, 2020, effective immediately thereafter, after a proposed in October 2019 confirmed the substance's continued abuse, no FDA-approved applications, and eight-factor analysis revealing persistent trafficking and health risks despite temporary controls. remains challenged by the rapid emergence of structural analogs, where illicit producers alter core scaffolds (e.g., or carboxamide groups) to circumvent listings, perpetuating the evolution of new psychoactive substances (NPS) faster than regulatory updates can address. Post-2017 scheduling correlated with AMB-FUBINACA becoming the predominant synthetic in seizures through early 2018, but detections declined thereafter as market shifts favored successors like MDMB-FUBINACA, though overall NPS innovation sustains enforcement demands.

International Controls and Bans

The World Health Organization's Expert Committee on Drug Dependence (ECDD) initiated a review of FUB-AMB (also known as AMB-FUBINACA or MMB-FUBINACA) during its 41st meeting in November 2018, following notifications under the 1971 , with recommendations forwarded to the UN Commission on Narcotic Drugs for potential scheduling in Schedule II. Despite this process, AMB-FUBINACA remains unscheduled under international drug control treaties as of the most recent WHO assessments. In the , the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) has monitored including AMB-FUBINACA through its but has not conducted a formal or issued a specific alert leading to EU-wide scheduling; however, national controls exist, such as inclusion in Germany's Anlage II (non-prescribable controlled substances) and bans in and . Several countries have implemented specific bans: classifies AMB-FUBINACA as a Schedule II substance under the . added it to its controlled substances list in August 2018 alongside other . In , AMB-FUBINACA was classified as a Class A controlled drug under the Misuse of Drugs Act following its association with over 70 deaths in 2017 and 2018, prompting urgent regulatory action amid outbreaks of severe intoxications. Post-control monitoring reveals persistent challenges, including detection of AMB-FUBINACA metabolites in from major cities in 2022, suggesting ongoing illicit use despite national bans. The WHO's ongoing critical reviews of synthetic analogs from 2023 to 2025 underscore the need for updated assessments, as structural modifications evade existing controls. Delays in achieving international enable cross-border flows, with variations in national scheduling facilitating trafficking from unregulated production hubs to controlled markets.

Challenges in Enforcement

The rapid evolution of synthetic agonists (SCRAs) like AMB-FUBINACA has outpaced legislative responses, with laboratories producing structural analogs such as MDMB-FUBINACA to circumvent specific bans. These modifications, often minor alterations to the or tail groups, allow new variants to evade targeted scheduling while retaining psychoactive potency, as evidenced by the emergence of over 20 new cannabinoids identified in in 2024 alone. Generic prohibition frameworks, such as the U.S. Analogue Act, provide partial deterrence by treating substantially similar substances as controlled, but producers adapt by synthesizing from unregulated precursors or semi-synthetic routes derived from legal cannabinoids. Detection and tracing of AMB-FUBINACA and its analogs present significant technical barriers, necessitating specialized analytical methods like (NMR) spectroscopy and (MS) for accurate identification amid complex matrices in seized materials. Routine screening techniques often fail to distinguish these compounds from herbal adulterants or other NPS, while opacity—characterized by decentralized online sales, DIY synthesis kits, and cross-jurisdictional supply chains—impedes source attribution and disruption efforts. Enforcement limitations are underscored by post-ban market shifts, with UNODC reporting 101 newly emerged NPS in 2024, including diversified SCRAs that escalated in potency to maintain appeal despite controls. Reliance on has inadvertently incentivized underground innovation, leading to "tail-less" and semi-synthetic variants that exploit regulatory gaps, as observed in detections from to 2025. This dynamic highlights the need for adaptive strategies beyond scheduling, such as enhanced precursor , though jurisdictional variances continue to facilitate evasion.