Tapentadol
[CAS# 175591-23-8]

Identification

• Classification: API >> Other chemicals
• Name: Tapentadol
• Synonyms: 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol
• Molecular Formula: C₁₄H₂₃NO
• Molecular Weight: 221.34
• CAS Registry Number: 175591-23-8
• EC Number: 605-757-6
• SMILES: CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H361-H411
• Safety Statements: P203-P264-P270-P273-P280-P301+P317-P318-P330-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Controlled Substance: DEA Drug Code Number: 9780

Discovery and Applications

Discovered in the early 2000s, tapentadol represents a new class of analgesics known as μ-opioid receptor agonists and norepinephrine reuptake inhibitors (MOR-NRIs). Its unique dual mechanism of action combines the opioid effects of μ-opioid receptor agonism with the noradrenergic effects of norepinephrine reuptake inhibition, providing effective pain relief with fewer side effects than traditional opioids.

A notable feature of tapentadol is its ability to effectively relieve a wide range of pain conditions. Whether used for acute pain management following surgery or trauma, or for chronic pain conditions such as neuropathic pain or osteoarthritis, tapentadol offers a variety of treatment options for patients experiencing pain of varying intensity and duration.

The analgesic effects of tapentadol are attributed to its dual mechanism of action, which targets multiple pain pathways in the central nervous system. By activating μ-opioid receptors, tapentadol modulates pain perception and transmission, providing rapid and effective pain relief. In addition, its inhibition of norepinephrine reuptake enhances descending inhibitory pathways, further dampening pain signals and improving pain control.

Tapentadol has several advantages over traditional opioid analgesics, especially in terms of safety and tolerability. Unlike pure μ-opioid receptor agonists, tapentadol produces fewer adverse reactions such as respiratory depression, sedation, and constipation due to its dual mechanism of action and lower affinity for opioid receptors. This reduced risk of adverse reactions makes tapentadol a preferred drug for patients who are sensitive to opioids or who are at risk for side effects of opioids.

In addition to its role in acute and chronic pain management, tapentadol may also be used to treat other conditions. Preliminary studies have shown that tapentadol may be effective in treating neuropathic pain such as diabetic neuropathy and postherpetic neuralgia. In addition, tapentadol's dual mechanism of action may be beneficial for psychiatric disorders such as depression and anxiety, although further research is needed to explore its potential in this regard.

In addition, tapentadol has also been studied for its role in mitigating opioid-related adverse reactions and reducing the risk of opioid abuse. Tapentadol is a μ-opioid receptor agonist that has lower abuse potential and respiratory depression than traditional opioids, offering a promising alternative for chronic pain patients at risk for opioid dependence or overdose.

References

2021. Comparison of opioid prescribing upon hospital discharge in patients receiving tapentadol versus oxycodone following orthopaedic surgery. International Journal of Clinical Pharmacy.
DOI: 10.1007/s11096-021-01290-7

2013. Three Newly Approved Analgesics: An Update. Anesthesia Progress.
DOI: 10.2344/0003-3006-60.4.178

2010. Safety and efficacy of tapentadol ER in patients with painful diabetic peripheral neuropathy: results of a randomized-withdrawal, placebo-controlled trial. Current Medical Research and Opinion.
DOI: 10.1185/03007995.2010.537589