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Technical Information
Formal Name N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-propanamide
CAS Number 437-38-7
Molecular Formula C22H28N2O
Formula Weight 336.5
Purity ≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/ml
SMILES
O=C(N(C1=CC=CC=C1)C2CCN(CCC3=CC=CC=C3)CC2)CC
InChi Code
InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
InChi Key
PJMPHNIQZUBGLI-UHFFFAOYSA-N
Regulatory Information
DEA Schedule II
Shipping & Storage Information
Storage -20°C Shipping
Room temperature in continental US; may vary elsewhere
Stability ≥ 5 years

Toxicity of fentanyl (CAS: 437-38-7) and valerylfentanyl (CAS: 122882-90-0): the first integrative in silico toxicology study with clinical and forensic implications

Fentanyl is a potent synthetic opioid, widely recognized for its dual role as a valuable medical analgesic and a significant public health threat. Initially developed in the 1960s for pain management, fentanyl has become a cornerstone in clinical medicine, particularly for surgical anesthesia and the management of severe, chronic pain due to its rapid onset and strong analgesic effects (Khatoon and Faudzi 2024). Its utility in pain management is complemented by various formulations, including transdermal patches, intravenous administration, and oral forms, making it versatile in clinical practice. Despite its medical benefits, fentanyl is also a leading cause of opioid-related overdose deaths worldwide. Its high potency, approximately 50–100 times stronger than morphine, renders it a frequent subject of misuse and a significant contributor to the ongoing opioid crisis (Borrego-Ruiz 2024). The illicit production and distribution of fentanyl, particularly through clandestine laboratories, have exacerbated the problem, leading to widespread abuse, overdose, and fatalities (Giorgetti et al. 2017). The public health impact of fentanyl misuse is profound, with opioid overdose deaths continuing to rise globally. In the USA alone, fentanyl has been implicated in a majority of opioid-related deaths in recent years (Tamburro et al. 2016). This crisis has prompted significant efforts in public health education, harm reduction, and the development of policies to monitor and control the distribution of opioids. Valerylfentanyl is a new psychoactive substance (NPS) and a member of the fentanyl analog family, which includes numerous potent substances with significant clinical and toxicological implications. Synthetic opioids like valerylfentanyl have been involved in the ongoing opioid crisis, contributing to a surge in overdose deaths worldwide. The toxicokinetics, side effects, and broader public health impacts of valerylfentanyl are areas of active research. Understanding these aspects is crucial for developing effective prevention and treatment strategies.

It should be noted that fentanyl analogs have been synthesized to circumvent legal restrictions and are often sold illicitly as recreational drugs. These substances pose substantial risks due to their high potency and potential for overdose. Valerylfentanyl’s effects are similar to other fentanyl analogs, but it is less potent in terms of affinity to opioid receptors (Åstrand et al. 2020). Known physicochemical data for fentanyl and valerylfentanyl have been chemically characterized in Table 1, based on available sources.

Table 1

Known physicochemical data for fentanyl and valerylfentanyl
Parameter
Fentanyl
Valerylfentanyl
IUPAC name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpentanamide
Molecular formula
C22H28N2O
C24H32N2O
Molecular structure
https://static-content.springer.com/image/art%3A10.1007%2Fs00204-025-04214-w/MediaObjects/204_2025_4214_Figa_HTML.gif
https://static-content.springer.com/image/art%3A10.1007%2Fs00204-025-04214-w/MediaObjects/204_2025_4214_Figb_HTML.gif
SMILES notation
O = C(CC)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3
CCCCC(= O)N(C1CCN(CCC2 = CC = CC = C2)CC1)C3 = CC = CC = C3
Molecular weight, g/mol
336.47
364.52
LogP (XLogP3)
3.94
4.28
Melting point
83–84 °C
Not available
Water solubility
Slightly soluble
Not available
CAS number
437-38-7
122,882–90-0
PubChem CID
3345
21,595,398
Legal status (UN)
Schedule I (narcotic)
Schedule I (narcotic)
This table aims to collate and present the sparse data that have been gathered from various databases (PubChem) (CompTox Dashboard 2023). Although numerous studies have investigated the pharmacological and toxicological properties of synthetic opioids, including various fentanyl analogs (Armenian et al. 2018; Williamson and Kermanizadeh 2024), there remains a substantial gap in the availability of fundamental toxicological data that would define a comprehensive toxicological profile for these substances. Current research tends to focus predominantly on acute toxicity and structural predictions of hazard potential, often leveraging computational methods (Bremer et al. 2016). However, essential studies that traditionally underpin toxicological assessment—such as those evaluating subchronic and chronic toxicity, developmental and reproductive toxicity, carcinogenicity, immunotoxicity, or neurotoxicity—are largely absent for emerging fentanyl analogs like valerylfentanyl.
This lack of data is particularly concerning given the wide spectrum of possible toxicological end points associated with synthetic opioids. The high potency, structural variability, and increasing appearance of new analogs on illicit markets elevate the urgency of systematically characterizing their risk profiles (Concheiro et al. 2018; Hasegawa et al. 2022). Despite the growing presence of such compounds in forensic casework and public health settings, the topic remains underrepresented in mainstream toxicological research, likely due to legal, ethical, and logistical constraints associated with traditional in vivo testing of highly potent, illicit substances.
At the same time, toxicological science is undergoing a methodological transformation, with a growing emphasis on alternative testing strategies aligned with the principles of the 3Rs (Replacement, Reduction, and Refinement of animal use). This has paved the way for integrated approaches to testing and assessment, including in silico modeling and computational toxicology, which offer promising, ethical, and rapid tools for hazard identification (Solimini et al. 2018). These methods can support early-phase prioritization and risk assessment by predicting toxicity end points across a wide range of biological systems, including organ-specific effects, genotoxicity, and cardiotoxicity. In the evolving landscape of toxicological research, new approach methodologies (NAMs) have emerged as critical tools for advancing safety assessments while reducing reliance on traditional animal testing.
A particularly important, yet often underestimated tool within NAMs is the use of in silico methods. These are computer-based approaches that use algorithms, models, and simulations to predict the toxicological properties of chemical substances based on their molecular structure, known biological activity, and chemical similarity to known compounds. In silico tools include quantitative structure–activity relationships (QSAR), read-across models, machine learning algorithms, and molecular docking, among others. They offer the ability to rapidly screen large numbers of chemicals, identify potential hazards early, and prioritize substances for further testing. Among these, in silico methods should serve as the fundamental first step in toxicity evaluation. These computational techniques allow for the early identification of potentially hazardous substances through predictive modeling and simulation of chemical behavior, enhancing the efficiency and ethical standards of toxicological research (Roberts 2024; Ram et al. 2022; Hartung 2009; Najjar et al. 2023). Based on this rationale, the core idea of the current study was to employ an integrated in silico approach for the prediction of key toxicity end points of fentanyl and its structural analog, valerylfentanyl. This strategy involved the sequential application of various in silico tools to estimate multiple toxicological parameters, including acute toxicity, organ-specific effects, irritation, genotoxicity, and cardiotoxicity, with direct relevance to both clinical and forensic toxicology contexts. The concept of conducted in silico research is presented as a workflow diagram in Fig. 1, illustrating the integrated strategy applied for toxicity prediction.

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