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Thenylfentanyl(CAT: I037199) is a synthetic opioid analgesic and a structural analog of fentanyl, known for its high potency as a μ-opioid receptor agonist. It exhibits strong analgesic effects by modulating opioid receptor activity, making it relevant in pain management and neuroscience research. Thenylfentanyl is often studied to understand opioid receptor interactions, tolerance, and dependency mechanisms. Due to its potency, it serves as a model compound for developing safer analgesics and exploring strategies to mitigate opioid-related side effects. Thenylfentanyl is a critical tool for advancing opioid pharmacology and therapeutic research.

CAS Number 122861-39-6
Synonyms Thenylfentanyl
Molecular Formula C19H24N2OS
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name N-Phenyl-N-(1-(2-thienylmethyl)-4-piperidyl)propanamide
InChI InChI=1S/C19H24N2OS/c1-2-19(22)21(16-7-4-3-5-8-16)17-10-12-20(13-11-17)15-18-9-6-14-23-18/h3-9,14,17H,2,10-13,15H2,1H3
InChIKey JSOSWRYHPGIWGT-UHFFFAOYSA-N
SMILES CCC(N(C1=CC=CC=C1)C2CCN(CC3=CC=CS3)CC2)=O
Chemistry Calculators Dilution Calculator
In vivo Formulation Calculator
Molarity Calculator
Molecular Weight Calculator
Reconstitution Calculator

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Thenylfentanyl is an analogue of fentanyl where the phenethylamine side-chain has been replaced by a thiophenylmethyl group. It was temporarily scheduled by the Drug Enforcement Administration in 1985,[1] due to fears it would be used as a designer drug. But in 2010 the DEA acknowledged it was essentially inactive.[2] Subsequently, the substance was since deregulated.

The legality of fentanyl analogues vary by country. In the United States, thenylfentanyl is unscheduled.

Thenylfentanyl Powder is a synthetic opioid

compound and structural analog of fentanyl, a drug known for its powerful pain-relieving properties and high abuse potential. Unlike some other fentanyl derivatives, thenylfentanyl has little to no recognized clinical use and is primarily known through its appearance in chemical research, forensic investigations, and sometimes as an illicit substance. Although not as potent as some of its analogs (like carfentanil or acetylfentanyl), thenylfentanyl still poses serious health risks, especially due to its potential for respiratory depression and overdose.

Chemical and Pharmacological Background

Thenylfentanyl, chemically named N-phenyl-N-[1-(2-thenyl)-4-piperidinyl]propanamide, differs from fentanyl by incorporating a thenyl (thiophen-2-ylmethyl) group in its structure. This subtle modification may reduce its opioid potency compared to traditional fentanyl, but it still acts on the mu-opioid receptors in the central nervous system—responsible for pain relief, euphoria, and sedation. It typically appears as a white to off-white crystalline powder and may be sold online or found in research chemical markets. However, its effects, potency, and toxicity are not well studied, making it highly unpredictable in real-world use.Health Risks and ToxicityEven though thenylfentanyl is believed to be less potent than fentanyl, it remains potentially lethal if misused. Key health risks include:Respiratory depression – the primary cause of death in opioid overdosesLack of clinical data, leading to unpredictable onset and durationIncreased danger when mixed with stronger opioids or sedativesSevere withdrawal symptoms in dependent individualsOverdose treatment may require multiple doses of naloxone (Narcan), especially if the powder is adulterated with more potent analogsIts presence in illicit drug mixtures raises concerns for accidental exposure and unintentional overdose.Legal StatusThenylfentanyl occupies a grey area in drug regulation in some countries but is increasingly being controlled under analogue laws:United States: Not specifically listed but may be prosecuted under the Federal Analogue ActUnited Kingdom: Likely covered under Class A drugs as a fentanyl analogCanada & Australia: Subject to control due to structural similarity to fentanylChina & EU: Varies by country, but generally restricted or bannedDue to growing concerns over designer opioids, many countries are moving toward blanket bans on entire chemical families, including thenylfentanyl.

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status
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Chemical and physical information
Formula: C22H28N2O4S

Molar mass: 416.54 g·mol?1

see
Sufentanil
List of painkiller analogues

Source and Classification

Thenylfentanyl is classified as an N-arylalkylamide derivative of norfentanyl. It is also recognized as a structural isomer of acetylthiofentanyl. The compound’s chemical formula is C19H24N2OS, with a molar mass of approximately 328.47 g/mol  . Its IUPAC name reflects its chemical structure, although specific identifiers such as CAS number and PubChem CID are not universally standardized across all databases  .

Synthesis Analysis

Methods and Technical Details

The synthesis of Thenylfentanyl can be approached through various chemical pathways, often involving modifications to existing fentanyl analogues. One notable method includes de-thiophenylmethylation of Thenylfentanyl to produce norfentanyl, followed by amination using phenethyl bromide to yield fentanyl. This synthetic route illustrates the compound’s potential utility in synthesizing other opioids .

Molecular Structure Analysis

Structure and Data

The molecular structure of Thenylfentanyl features a thiophenylmethyl group attached to a piperidine ring, characteristic of many fentanyl analogues. The structural formula can be represented as follows:

Thenylfentanyl C19H24N2OS

The structural representation highlights the presence of sulfur within the thiophenyl group, which distinguishes it from other analogues that may not contain this element. The compound’s three-dimensional conformation can be analyzed using molecular modeling software for further insights into its spatial arrangement  .

Chemical Reactions Analysis

Reactions and Technical Details

Thenylfentanyl can undergo various chemical reactions typical for amides and aryl derivatives. Key reactions include:

  • Hydrolysis: Under acidic or basic conditions, Thenylfentanyl can hydrolyze to yield corresponding acids and amines.
  • Reduction: The compound may be reduced using lithium aluminum hydride or similar reducing agents to form amine derivatives.

These reactions are significant for understanding the reactivity profile of Thenylfentanyl and its potential transformations in synthetic organic chemistry .

Mechanism of Action

Process and Data

Thenylfentanyl’s mechanism of action primarily involves interaction with mu-opioid receptors in the central nervous system. Although it has reduced efficacy compared to fentanyl, it still binds to these receptors, which are responsible for mediating pain relief and euphoric effects associated with opioids. The diminished activity suggests that while it may exhibit some opioid-like effects, it is less potent than other analogues  .

Physical and Chemical Properties Analysis

Physical and Chemical Properties

Thenylfentanyl exhibits several notable physical properties:

Chemical properties include stability under standard laboratory conditions but may vary under extreme pH or temperature conditions  .

Applications

Scientific Uses

While Thenylfentanyl itself has limited application due to its low potency, its structural characteristics make it relevant for research in opioid pharmacology. It could serve as a precursor in the synthesis of more potent opioids or be used in studies aimed at understanding opioid receptor interactions and developing safer analgesics with reduced side effects  .

Properties

CAS Number

122861-39-6

Product Name

Thenylfentanyl

IUPAC Name

N-phenyl-N-[1-(thiophen-2-ylmethyl)piperidin-4-yl]propanamide

Molecular Formula

C19H24N2OS

Molecular Weight

328.5 g/mol

InChI

InChI=1S/C19H24N2OS/c1-2-19(22)21(16-7-4-3-5-8-16)17-10-12-20(13-11-17)15-18-9-6-14-23-18/h3-9,14,17H,2,10-13,15H2,1H3

InChI Key

JSOSWRYHPGIWGT-UHFFFAOYSA-N

Canonical SMILES

CCC(=O)N(C1CCN(CC1)CC2=CC=CS2)C3=CC=CC=C3

Uses

In much the same way that benzylfentanyl can be used to synthesize fentanyl, thenylfentanyl could ostensibly be used for the same purpose. In such a procedure, thenylfentanyl would first be de-thiophenylmethylated to norfentanyl. This would be followed by amination to fentanyl using phenethyl bromide.[3]

Chemistry

Statue of Paul Janssen

Thenylfentanyl is a N-arylalkylamide derivative of norfentanyl. The substance is also a structural isomer of acetylthiofentanyl, wherein a methyl group on the thiophene sidechain has been relocated to the carboxamide group nearest the aniline. It is due to this reduced sidechain length that Thenylfentanyl has dramatically diminished MOR activity compared to other fentanyl analogues. Many of fentanyl’s analogues were discovered by Belgian physician Paul Janssen.

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