SR-17018

CAS Number 2134602-45-0
Molecular Formula C₁₉H₁₈Cl₃N₃O
Molecular Weight 410.7 g/mol
Purity ≥99.0%
Appearance White, powdery solid

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Product Description

SR-17018 is a synthetic organic compound which belongs to the benzimidazolone chemical class and is primarily used in scientific research. Structurally, it features a dichlorinated benzimidazolone core linked to a chlorobenzyl-piperidine group. SR-17018 is a potent GPR55 antagonist, making it an invaluable tool for researchers studying the role of GPR55 in various biological processes, including pain perception, bone density regulation, and cancer cell proliferation. Additionally, SR-17018 is also a biased μ-opioid receptor agonist, designed to preferentially activate G-protein signaling over β-arrestin2 recruitment. This property allows it to produce morphine-like analgesia with reduced side effects such as respiratory depression and tolerance development. Preclinical studies have shown that SR-17018 exhibits analgesic effects with lower intrinsic efficacy in non-human primates compared to traditional opioids, making it a promising candidate for further research in pain management.

Synthesis Methods

  • Synthetic Origin: SR-17018 is a synthetic organic compound belonging to the benzimidazolone chemical class.

  • Structure: It features a dichlorinated benzimidazolone core linked to a chlorobenzyl-piperidine group.

  • Synthesis Details: Specific synthesis methods are not detailed in the provided files, but it is known to be a chemically synthesized compound.

Research Findings

  • In Vivo Efficacy: Studies in non-human primates show that SR-17018 has low intrinsic efficacy, similar to buprenorphine, which explains its improved side-effect profile.

  • Phosphorylation Studies: SR-17018 induces a unique phosphorylation pattern on the μ-opioid receptor, with delayed dephosphorylation kinetics, suggesting a slow off-rate and potential for sustained receptor activation.

  • Behavioral Assays: In animal models, SR-17018 exhibits reduced tolerance and dependence liability compared to morphine, with efficacy in neuropathic pain models where morphine is less effective.

Uses

  • Research Use: SR-17018 is primarily used for research purposes and is not approved for human or veterinary diagnostic or therapeutic use.

  • Pharmacological Studies: It is used to study the function of the μ-opioid receptor (MOR) and its biased signaling properties.

  • Pain Management Research: Investigated for its potential in managing pain with reduced side effects compared to traditional opioids.

  • Tolerance and Dependence Studies: Used to study the development of tolerance and dependence in animal models.

  • Comparative Studies: Used alongside other opioid modulators to understand receptor signaling and effects.

Biological and Pharmacological Properties

  • Pharmacological Activity: SR-17018 is a G-protein-biased μ-opioid receptor (MOR) agonist.

  • Bias Hypothesis: It is designed to preferentially activate G-protein signaling over β-arrestin2 recruitment, which is believed to mediate adverse effects such as respiratory depression.

  • Analgesic Effects: Produces morphine-like analgesia with reduced respiratory depression and lower development of tolerance.

  • Receptor Phosphorylation: Exhibits a unique phosphorylation pattern on the μ-opioid receptor, with delayed dephosphorylation kinetics.

  • Functional Profile: In non-human primates, SR-17018 shows low efficacy for activating the MOR receptor, similar to buprenorphine.

Properties and Characteristics of SR-17018

  • Chemical Formula: C₁₉H₁₈Cl₃N₃O

  • Molecular Weight: 410.7 g/mol

  • CAS Number: 2134602-45-0

  • IUPAC Name: 5,6-dichloro-3-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-1H-benzimidazol-2-one

  • Synonyms: 5,6-Dichloro Desmethylchlorphine, SR-17018

  • Physical State: Solid

  • Solubility: Soluble in DMF and DMSO (1 mg/ml), slightly soluble in ethanol, and soluble in DMSO:PBS (pH 7.2) at 0.33 mg/ml

  • Melting Point: Undetermined

  • Boiling Point: Undetermined

  • pH Value: Not applicable

  • Partition Coefficient (n-octanol/water): Not determined

  • Density: Not determined

  • Flash Point: Not applicable

  • Flammability: Not flammable

  • Explosion Limits: Not determined

  • Odor: Characteristic

  • Appearance: Solid powder

Safety and Handling

  • Handling: Should be handled by trained personnel in a laboratory setting using appropriate personal protective equipment (PPE) such as gloves and safety glasses.

  • Storage: Typically stored at low temperatures (e.g., -20°C) in a dry environment to ensure stability.

  • Hazards: Not classified as hazardous under the Globally Harmonized System (GHS).

  • First Aid: No special measures required for inhalation, skin contact, or eye contact. Fresh air and medical consultation are advised if symptoms persist after inhalation or swallowing.

Regulatory and Safety Information

  • Regulatory Status: Not listed under various regulatory frameworks such as IARC, NTP, OSHA, EPA, and TSCA.

  • Safety Data Sheet (SDS): Provided by Cayman Chemical Company, indicating that the substance is for research use only and not for human or veterinary diagnostic or therapeutic use.

  • Disposal: Smaller quantities can be disposed of with household waste, and uncleaned packaging must be disposed of according to official regulations.

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