Benzedrone Stats & Data
Cc1ccc(cc1)C(=O)C(C)NCc1ccccc1KWHZRPBDEAQYDE-UHFFFAOYSA-NPharmacology
DrugBankDescription
Commonly known as 4-methylbenzylidene-camphor (4-MBC), enzacamene is a camphor derivative and an organic chemical UV-B filter. It is used in cosmetic products such as sunscreen to provide skin protection against UV rays. While its effects on the human reproductive system as an endocrine disruptor are being investigated, its use in over-the-counter and cosmetic products is approved by Health Canada. Its tradenames include Eusolex 6300 (Merck) and Parsol 5000 (DSM).
Mechanism of Action
Enzacamene absorbs UV-B rays. It is proposed that enzacamene exerts estrogen-like activities in the same direction as endogenous estrogens via nonclassical estrogen signaling mechanisms that do not involve gene regulation by the nuclear ER . It binds to cytosolic estradiol binding sites of estrogen receptors with low to moderate affinity compared to that of the endogenous agonist. Based on the findings of a study with _Xenopus_ hepatocytes in culture, enzacamene has a potential to induce the ER gene only at higher concentrations (10–100 μmol/L). While enzacamene was not shown to activate estrogen-dependent gene transcription when tested in an ER reporter gene assay in yeast cells, it was demonstrated in _Xenopus_ hepatocytes cultures that activate ER-dependent signaling mechanisms leading to altered gene expression . In micromolar concentrations, enzacamene accelerates cell proliferation rate in MCF-7 human breast cancer cells .
Pharmacodynamics
Several studies suggest that enzacamene elicit estrogen-like effects. In prepubertal male rats exposed to enzacamene during embryonic and fetal development, decrease in testicular weight with decreased levels of LH, GnRH, and glutamate were observed; in comparison, there was an increase in LH, GnRH, and aspartate levels in peripubertal rats . These findings suggest that high concentrations of enzacamene during embryonic and fetal stage inhibits the testicular axis in male rats during the prepubertal stage and stimulates it during peripubertad stage . In a study of zebrafish (Danio rerio) embryo, exposure to enzacamene during early vertebrate development was associated with muscular and neuronal defects that may result in developmental defects, including a reduction in AChE activity, disorganized pattern of slow muscle fibers, and axon pathfinding errors during motor neuron innervation . Enzacamene displays a weak binding activity in receptors binding assays using the mammalian estrogen receptor (ER) .
Metabolism
Based on the findings of a rat pharmacokinetic study, it is proposed that absorbed enzacamene following oral administration undergo extensive first-pass hepatic metabolism . Following oral administration of enzacamene (4-MBC) in rats, detected metabolites in the plasma and urine were 3-(4-carboxybenzylidene)camphor and as four isomers of 3-(4-carboxybenzylidene)hydroxycamphor containing the hydroxyl group located in the camphor ring system with 3-(4-carboxybenzylidene)-6-hydroxycamphor as the major metabolite. However the blood concentrations of 3-(4-carboxybenzylidene)-6-hydroxycamphor were below the limit of detection following peak concentration . Via hydroxylation mediated by cytochrome P450 system, 3-(4-hydroxymethylbenzylidene)camphor is formed. This metabolite is further oxidized to 3-(4-carboxybenzylidene)camphor via oxidation of alcohol dehydrogenase and aldehyde dehydrogenase, and may be further hydroxylated to form 3-(4-carboxybenzylidene)-6-hydroxycamphor mediated by CYP450 system .
Absorption
The maximum plasma concentration of enzacamene was 16ng/mL in healthy female volunteers following daily whole-body topical application of 2mg/cm^2 of sunscreen formulation at 10% (weight/weight) for four days . Blood concentration of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, peaked within 10 h after oral administration of enzacamene .
Toxicity
Oral LD50 and dermal LD50 in rat are reported to be 10,000 mg/kg . Oral TDLO in rat is 7 mg/kg . Oral and subcutaneous TDLO following continuous administration in rat are 476 mg/kg/4D and 4 mg/kg/2D, respectively . Cases of overdose have not been reported for enzacamene. Enzacamene is reported to be an endocrine disruptor that alters the reproductive axis.
Indication
Indicated for use as an active sunscreen agent.
Half-life
The half life of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, displayed half-lives of approximately 15 h after reaching peak plasma concentrations after oral administration in rats .
Elimination
The urine concentration of 4 ng/mL and 4 ng/mL of enzacamene were observed in female and male volunteers, respectively . In a rat pharmacokinetic study, most of orally administered enzacamene was recovered in in feces as 3-(4-carboxybenzylidene)camphor and, to a smaller extent, as 3-(4-carboxybenzylidene)-6-hydroxycamphor . Glucuronides of both metabolites were also detectable in faces . In urine, one isomer of 3-(4-carboxybenzylidene)hydroxycamphor was the predominant metabolite 3-(4-carboxybenzylidene)-6-hydroxycamphor, the other isomers and 3-(4-carboxybenzylidene)camphor were only minor metabolites excreted with urine . Enterohepatic circulation of glucuronides derived from the two major 4-MBC metabolites may explain the slow excretion of 4-MBC metabolites with urine and the small percentage of the administered doses recovered in urine .
Effect Profile
CuratedStrong euphoria and anxiety/jitters with moderate focus, mild stimulation
Tolerance & Pharmacokinetics
drugs.wikiTolerance Decay
Pattern inferred from cathinone/amphetamine use reports: tolerance builds over multi‑day use and decays over 1–3 weeks of abstinence. Data quality is anecdotal; avoid consecutive‑day or binge use.
Cross-Tolerances
Harm Reduction
drugs.wiki• Identity: The EU drug agency lists Benzedrone (4‑MBC) as an N‑benzyl analogue of mephedrone; do not confuse it with the sunscreen ingredient 4‑methylbenzylidene camphor, which is also abbreviated “4‑MBC.” This matters for checking and labeling to avoid dangerous mix‑ups.
• Limited human data: There are no human pharmacokinetic or clinical studies for 4‑MBC. Treat all dose and duration figures as uncertain and start low, go slow. Group‑level harm data for synthetic cathinones (e.g., mephedrone) indicate short action and redosing pressure.
• Potency and redosing: Multiple user reports describe 4‑MBC as weak or inactive at doses that would be active for 4‑MMC, leading to high‑dose redosing attempts. Avoid chasing effects; set a pre‑planned maximum and spacing (≥3 h) to limit cumulative cardiovascular strain.
• Route harms: Insufflation is commonly reported as extremely painful and irritating with nosebleeds; oral administration is generally preferred for harm reduction if one chooses to proceed. Consider nasal care or avoid intranasal use entirely.
• Cardiovascular/thermoregulatory risk: As a stimulant cathinone, expect increased heart rate, blood pressure, and temperature. Maintain hydration with electrolytes, take cooling breaks, and avoid hot environments—guidance extrapolated from cathinone group warnings and emergency department data.
• Injection risks: Cathinone injection is linked with high‑risk practices and outbreaks (HIV/HCV) in Europe; avoid injecting 4‑MBC. If someone injects stimulants, use sterile equipment each time and do not share.
• Polydrug interactions: Combining with MAOIs is high‑risk; combining with other stimulants or serotonergic agents (e.g., 4‑FA, tramadol, high‑dose caffeine) increases risks of hypertensive events, arrhythmias and, with serotonergics, serotonin toxicity. Use of authoritative combo charts can help flag red‑zones but is not a substitute for clinical data.
• Adulteration/mis‑selling: Synthetic cathinones are frequently mis‑sold or substituted; confirm identity with drug checking where available. Cathinones often react purple with Morris reagent; do not rely on a single reagent. Lab testing services provide the most reliable identification.
• Sleep and comedown: Residual stimulation and insomnia are common; allow a long, calm wind‑down window and avoid driving or safety‑critical tasks for at least 8–12 h after last dose. This aligns with stimulant HR practice and user narratives.
• “Pro‑drug” claim is unproven: Some forum speculation suggests possible N‑debenzylation to 4‑MC or 4‑MMC, but no in‑vivo evidence confirms this; do not assume mephedrone‑like potency or safety.
• Population cautions: People with cardiovascular disease, hypertension, arrhythmia history, or seizure disorders, and those on serotonergic or MAOI medications, face elevated risks and should avoid use. This is based on synthetic cathinone class harms.
References
Drugs.wiki References
- EUDA/EMCDDA – Perspectives on drugs: injection of synthetic cathinones (includes Benzedrone/4‑MBC in structural table)
- EUDA – Synthetic cathinones drug profile (group harms, short action, redosing)
- Bluelight – Benzedrone (4‑MBC) personal experiences (harsh insufflation, weak effects)
- Drugs‑Forum – 4‑MBC (4‑methyl‑N‑benzylcathinone) info thread (weak potency, naming cautions)
- TripSit – Drug combinations chart (general MAOI/stimulant and stimulant/serotonergic cautions)
- TripSit – Combination chart announcement (reference for use of chart)
- r/ReagentTesting – community guidance on cathinone reagent reactions (Morris)