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BDPC
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BDPC
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BDPC
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Identifiers
  • 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H28BrNO
Molar mass402.376 g·mol−1
3D model (JSmol)
Melting point208 to 210 °C (406 to 410 °F)
  • CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br
  • InChI=1S/C22H28BrNO/c1-24(2)22(19-8-10-20(23)11-9-19)16-14-21(25,15-17-22)13-12-18-6-4-3-5-7-18/h3-11,25H,12-17H2,1-2H3 checkY
  • Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N checkY
  (verify)

BDPC (systematic name 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known as bromadol) is a potent fully synthetic opioid with a distinctive arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s.[1] Initial studies estimated that it was around 10,000 times the potency of morphine in animal models.[2] However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active trans-isomer.[3] This drug was first seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada,[4] and has reportedly continued to be available on the designer drug market internationally.[5][6] Analogues where the para-bromine is replaced by chlorine or a methyl group retain similar activity, while the meta-hydroxyl derivative demonstrated robust antagonist activity.[7][8]

p-methyl analogue of BDPC
p-chloro analogue of BDPC. [1]
m-hydroxy analogue of BDPC. [2]

See also

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References

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BDPC

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BDPC, systematically named 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol and commonly referred to as bromadol, is a fully synthetic distinguished by its scaffold. Developed by medicinal chemist Daniel Lednicer at the Upjohn Company during the as part of efforts to identify novel pain-relieving agents, the compound demonstrated extraordinary potency in preclinical evaluations. Early animal studies reported analgesic effects up to 10,000 times stronger than , though refined assays later established the trans isomer's potency at approximately 500-fold that of relative to benchmarks. Despite this efficacy, BDPC's narrow safety margin, marked by severe respiratory depression at low doses, precluded its progression to human trials or therapeutic approval. In contemporary contexts, it has surfaced sporadically as a and new psychoactive substance in unregulated markets, heightening overdose risks amid the broader synthetic crisis due to inconsistent dosing and adulteration.

Chemistry

Structure and nomenclature

BDPC, systematically named 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol, possesses the molecular formula C22_{22}H28_{28}BrNO and a molecular weight of 402.4 g/mol. The core structure consists of a ring bearing a and a 2-phenylethyl substituent at position 1, alongside a 4-bromophenyl group and a dimethylamino group both attached to position 4. This 4,4-disubstituted configuration, combined with the tertiary and phenolic-like , contributes to its classification as a synthetic structurally related to derivatives but distinguished by the equatorial hydroxy and axial chain positioning in its trans . The compound is commonly referred to as bromadol or BDPC, with "BDPC" serving as a derived from early pharmacological designations, while "bromadol" highlights the brominated phenyl moiety. The emphasizes the parent chain, reflecting standard nomenclature for such tertiary alcohols with quaternary carbon substitutions. is specified as trans for the pharmacologically active form, where the 4-substituents adopt a configuration optimizing receptor binding affinity. Analogs such as 4-methylbromadol replace the bromo with methyl, altering potency but retaining the core scaffold.

Physical and chemical properties

BDPC, or 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol, exists as a solid at , typically appearing white to off-white. Its molecular formula is C22_{22}H28_{28}BrNO, with a molecular weight of 402.4 g/mol. The compound exhibits a characteristic and is not flammable under standard conditions. Experimental melting and boiling points for the free base remain undetermined, though the hydrochloride salt shows distinct values: 242–243 °C for the trans isomer and 208–210 °C for the cis isomer as the hydrated form. Solubility is low in but higher in organic solvents like and , consistent with its lipophilic nature (predicted logP ≈ 5.1). is predicted at approximately 1.28 g/cm³, and the at around 489 °C under standard pressure. Chemically, BDPC features a tertiary amine moiety that imparts basicity (predicted pKa ≈ 14.8 for the conjugate acid of the alcohol, though amine pKa likely higher) and a tertiary alcohol group resistant to typical oxidation but potentially susceptible to under acidic conditions. The is low at 23.47 Ų, aiding membrane permeability. Limited experimental data exists due to its status as a opioid analog, with most properties derived from computational models or salts. Stability is maintained under refrigerated storage away from light and moisture, as per supplier guidelines.

Synthesis

Laboratory synthesis methods

The laboratory synthesis of BDPC, also known as bromadol, was originally developed by Daniel Lednicer at the Company in the late as part of efforts to create potent opioid analgesics. This method employs a five-step sequential organic synthesis starting from the monoketal of cyclohexane-1,4-dione, which serves as a protected precursor to enable regioselective introduction of substituents at the 4-position (geminal 4-bromophenyl and dimethylamino groups) and the 1-position (hydroxy and 2-phenylethyl groups). The approach leverages organometallic additions, nucleophilic substitutions, and deprotection steps typical for constructing substituted cyclohexanols with analgesic activity, yielding the trans isomer as the primary product. Detailed procedures for this synthesis, including variations for analogous 4-amino-4-arylcyclohexanols, are documented in German patent DE 2839891, filed by Lednicer, which describes the transformation of cyclohexanedione derivatives into the target compounds via aryl Grignard reagents and amine incorporation. Subsequent laboratory adaptations have focused on optimizing yields and purity for research purposes, often using standard reagents like p-bromophenylmagnesium bromide for arylation and dimethylamine for amination, followed by phenethyl Grignard addition to the intermediate ketone. These methods prioritize stereoselectivity to favor the pharmacologically active trans configuration, though illicit or non-patented reproductions may vary in efficiency and safety. No large-scale industrial processes were pursued due to the compound's extreme potency and developmental discontinuation.

Pharmacology

Pharmacodynamics

BDPC, also known as bromadol, functions primarily as an at the μ-opioid receptor (MOR), mediating its pharmacological effects through inhibition of , hyperpolarization of neurons via activation, and reduction of release. This binding profile underlies its potent properties, as well as characteristic opioid effects including , , respiratory depression, miosis, and gastrointestinal motility inhibition. In vitro functional assays conducted in human embryonic kidney (HEK293T) cells expressing human MOR revealed BDPC's high potency, with EC50 values of 1.89 nM (95% CI: 1.23–2.93 nM) for β-arrestin 2 recruitment and 3.04 nM (95% CI: 1.48–6.28 nM) for mini-Gi protein recruitment. Efficacy assessments showed Emax values of 182% relative to hydromorphone for β-arrestin 2 and 462% for mini-Gi, indicating BDPC acts as a highly efficacious, full without pronounced biased signaling toward either pathway. These metrics position BDPC as 7.6- to 10.8-fold more potent than in these cellular models. Animal studies corroborate this potency; in a mouse hot plate assay, BDPC demonstrated analgesic effects approximately 2.9 times greater than fentanyl. Broader evaluations from its developmental research at Upjohn estimated analgesic potency at around 500 times that of morphine, equivalent to roughly three times fentanyl's, though early reports of up to 10,000-fold morphine equivalence appear overstated based on subsequent data. No significant affinity or activity at δ- or κ-opioid receptors has been documented, suggesting selectivity for MOR.

Pharmacokinetics

Pharmacokinetic data for BDPC (also known as bromadol) are not available in published scientific literature. No studies have reported on its absorption, distribution, , or profiles. This absence of information stems from BDPC's development as a compound without progression to clinical trials or therapeutic applications, limiting systematic investigation into its handling by the body. Given its structural similarity to lipophilic opioids, rapid tissue penetration and hepatic might be anticipated, but such inferences remain unverified without . The lack of pharmacokinetic characterization contributes to uncertainties regarding dosing, duration of action, and potential accumulation in repeated use.

Development and history

Research at

BDPC, systematically known as trans-4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol, was synthesized in the 1970s by Daniel Lednicer and colleagues at The Company as part of a systematic exploration of 4-amino-4-arylcyclohexanone derivatives for activity. This sought to identify potent, non-addictive opioids by modifying structural features of known , building on earlier work with -based scaffolds. The team prepared a series of compounds varying the aryl substituent at the 4-position, the amino group, and the substituent at the 1-position of the ring, evaluating their potency in models such as the hot-plate and phenylquinone writhing assays. Key findings from the aryl ring modification study highlighted that para-substituted phenyl rings enhanced potency, with the 4-bromophenyl variant demonstrating exceptional activity. Subsequent modifications to the , reducing it to a hydroxyl in BDPC, further optimized the while maintaining high efficacy. Initial evaluations at reported BDPC's potency as up to 10,000 times that of in certain animal tests, positioning it among the most potent opioids identified at the time. However, later pharmacological assessments have revised this estimate to approximately 500 times 's potency and three times that of , attributing the discrepancy to assay variability and overestimation in early screens. Despite its promising preclinical profile, did not advance BDPC to clinical trials, likely due to challenges with , including narrow safety margins observed in studies common to high-potency opioids of this era. The compound's synthesis involved standard ketone alkylation followed by and stereoselective reduction, yielding the trans predominant for activity. These efforts contributed to broader understanding of opioids but underscored the difficulties in balancing potency with selectivity and reduced side effects.

Subsequent studies and interest

Following the initial research at in the 1970s, BDPC did not progress to clinical trials, likely due to its extreme potency and associated risks, with indicating analgesic effects up to 10,000 times that of , though later estimates revised this to approximately 500 times and three times . Limited follow-up pharmacological investigations occurred until the 2010s, when BDPC reemerged in discussions of novel synthetic opioids amid the broader opioid crisis, prompting renewed scrutiny of non-fentanyl alternatives on illicit markets. A 2018 review highlighted BDPC (bromadol) as a structurally distinct from the series, noting its potential for euphoric effects and recommending close monitoring due to early indicators of recreational interest in online psychonaut communities and isolated drug seizures, including one confirmed case in . This interest stemmed from its high mu- receptor () agonism, distinct from analogs, positioning it as a candidate for diversion in search of potent, non-scheduled alternatives. Subsequent studies in the late 2010s and early 2020s confirmed BDPC's exceptional MOR efficacy, exceeding reference agonists like DAMGO in functional assays, with Emax values among the highest in panels of emerging opioids, underscoring its pharmacological potency but also overdose risks given sparse human data. These findings, derived from recombinant cell models, emphasized BDPC's full agonism without detailed follow-up, reflecting caution over its compared to established opioids. No large-scale clinical or epidemiological studies have emerged, and its presence remains marginal in forensic reports, with interest largely confined to monitoring rather than therapeutic exploration.

International controls

BDPC (also known as bromadol) is not currently scheduled under any of the international drug control conventions, including the 1961 (as amended), the 1971 , or the 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. The (INCB) has identified BDPC as a non-fentanyl of concern in its monitoring of new psychoactive substances, noting its structural relation to historical research opioids and potential for abuse, but has not recommended international scheduling as of the latest available assessments in 2023. Emerging reports of BDPC appearing in illicit markets, particularly as a purported alternative to controlled synthetic opioids such as following its international scheduling in 2018, have prompted calls for pre-emptive monitoring and potential future controls through international early warning systems. No such controls have been enacted by the UN Commission on Narcotic Drugs as of October 2025.

National regulations

In the United States, BDPC (also known as bromadol or 4-(4-bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol) is not explicitly scheduled under federal controlled substances law administered by the (DEA). However, it has been added to Schedule I of 's controlled substances list effective March 2018 through Senate File 2578, which responded to law enforcement seizures of the substance as a synthetic . Schedule I classification in prohibits manufacture, possession, distribution, or use outside of limited research exemptions, reflecting its high potential for abuse and lack of accepted medical use. No other national-level regulations explicitly scheduling BDPC were identified in primary government sources across major jurisdictions such as , the member states, or as of 2025. In contexts where BDPC appears in illicit markets, it may be prosecuted under broader analog acts—such as the U.S. —or generic new psychoactive substances frameworks if intended for human consumption and structurally analogous to scheduled opioids. Monitoring by agencies like the DEA continues due to its potency and emerging recreational interest, but federal temporary or permanent scheduling has not occurred.

Risks and adverse effects

Overdose potential

BDPC exhibits high overdose potential due to its exceptional potency as a μ-opioid receptor , with animal studies indicating an analgesic efficacy approximately 500 times greater than and roughly three times that of . This narrow heightens the risk of respiratory depression, the primary mechanism of , where excessive dosing suppresses central respiratory drive, leading to hypoxia, , and death if untreated. As a with limited human pharmacokinetic data, BDPC's bioavailability and duration of action remain poorly characterized, complicating safe dosing and increasing accidental overdose likelihood, particularly in illicit formulations where purity varies. Early estimates overstated its potency at 10,000 times using less precise methods, but refined assays confirm substantial lethality risk comparable to ultra-potent synthetics like . No confirmed human overdoses have been publicly reported as of 2023, though its detection in U.S. illicit opioid samples alongside suggests emerging misuse potential. Overdose symptoms mirror those of other full μ-agonists: , , , and , with as the antidote, though multiple doses may be required given BDPC's potency exceeding fentanyl's. emphasizes testing for adulterants, as BDPC's structural similarity to derivatives may confound detection in standard screens.

Toxicity profile

BDPC, as a highly potent μ- receptor , demonstrates an EC50 of 1.89 nM in GTPγS binding assays, surpassing the potency of many synthetic opioids and implying a substantial overdose risk due to its narrow safety margin. This pharmacological profile predicts classic opioid toxicities, including profound respiratory depression, sedation, , , and in overdose scenarios, with fatalities primarily attributable to hypoxia from suppressed ventilation. Empirical toxicity data specific to BDPC are limited, with no established LD50 values or comprehensive pharmacokinetic studies available in peer-reviewed literature, reflecting its status as an obscure rather than a clinically developed . Detection of BDPC in five adverse event cases submitted to the European Monitoring Centre for Drugs and Drug Addiction's database since January 2018 underscores potential real-world harm, though detailed clinical outcomes—such as dose-response relationships or co-intoxicants—remain undisclosed. Chronic exposure risks mirror those of other full μ-opioid agonists, encompassing tolerance, , withdrawal symptoms (e.g., , , ), and secondary effects like and , exacerbated by BDPC's structural novelty and lack of antidote optimization beyond . Illicit formulations may compound toxicity through impurities or adulteration, as evidenced by street reports linking BDPC to heroin-fentanyl mixtures, heightening unpredictability in non-laboratory settings. Ongoing forensic surveillance is advised given rising interest in this non-fentanyl opioid alternative.
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