Structure via PubChem · Public domain (PubChem)
tapentadol
Sign in to saveAlso known as BN-200, CG-5503, Nucynta®, Palexia®
Tapentadol, sold under the brand names Nucynta and Palexia among others, is a synthetic opioid analgesic with a dual mode of action as a highly selective full agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Tapentadol is used medically for the treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug.
Chemical data
- Formula
- C14H23NO
- Molecular weight
- 221.34 g/mol
- IUPAC name
- 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
- SMILES
- CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C
- InChIKey
- KWTWDQCKEHXFFR-SMDDNHRTSA-N
- XLogP
- 3.5
- Polar surface area
- 23.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
837 papers- Tapentadol Versus Tramadol: A Narrative and Comparative Review of Their Pharmacological, Efficacy and Safety Profiles in Adult Patients.Drugs · 2021
- Tapentadol: A Comprehensive Review of Its Role in Pain Management.Cureus · 2024
- Tapentadol for the management of cancer pain in adults: an update.Current opinion in supportive and palliative care · 2023
- Tapentadol: an overview of the safety profile.Journal of pain research · 2019
- Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings.Drug design, development and therapy · 2023
via PubMed
Wikidata facts
- Mass
- 221.177964
Show 5 more facts
- chemical formula
- C₁₄H₂₃NO
- Commons category
- Tapentadol
- isomeric SMILES
- CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C
- canonical SMILES
- CCC(C1=CC(=CC=C1)O)C(C)CN(C)C
- defined daily dose
- 0.4
via Wikidata · CC0
~21 min read
Article
13 sectionsContents
- Medical use
- Contraindications
- Adverse effects
- Addiction and abuse
- Dependence and withdrawal
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- History
- Abuse and controls
- Veterinary use
- References
Tapentadol, sold under the brand names Nucynta and Palexia among others, is a synthetic opioid analgesic with a dual mode of action as a highly selective full agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Tapentadol is used medically for the treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug.
Frequently reported adverse effects include euphoria, constipation, nausea, vomiting, headaches, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating. More severe adverse reactions can occur, including addiction and dependence, substance abuse, respiratory depression, and an elevated risk of serotonin syndrome. Concurrent use of tapentadol with serotonergic drugs or central nervous system depressants – including alcohol, cannabis, benzodiazepines, and other opioids – can heighten the risks of excessive serotonin accumulation, profound sedation, dangerously slowed breathing and death.