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Opioid

Tapentadol

Also called Nucynta, Palexia, Yantil, Yantil SR

Original Wikipedia articleen.wikipedia.org/wiki/Tapentadol revision used (24 October 2026)

Why a "revision used" link? Anyone can edit Wikipedia at any time, so the article you open today may not say what it said when we read it. This link opens the exact version we read on 24 October 2026, frozen as it was. It is the only way to check that every quote on this page matches its source word for word. Newer versions may correct or change things. When we re-check this page against a newer version, the edit log records it. How we cite

Part of the metabolic pathway of Tapentadol. See the timeline on the metabolic highway.

Enzymes that break it down: CYP2C9, CYP2C19 and CYP2D6. Wikipedia’s drug infobox says: “Hepatic (mostly via glucuronidation but also by CYP2C9, CYP2C19, CYP2D6)” (revision 1378730489).

Common dose · Oral50–75 mg PW
Onset15–30 minutes PW
Total4–6 hours PW

Dosage

When sources disagree, both rows are shown as published. Nothing is averaged or merged.

Oral

SourceThresholdLightCommonStrongHeavy
PsychonautWiki12.5 mg PW25–50 mg PW50–75 mg PW75–150 mg PW150 mg+ PW
TripSit–25–50 mg TS50–75 mg TS75–150 mg+ TS–

NOTE: Doses are for no tolerance. Insufflated administration is ineffective. TS

TripSit dose text

TripSit's factsheet also states its doses as text.

Oral Light: 25-50mg Common: 50-75mg Strong: 75-150mg+ | NOTE: Doses are for no tolerance. Insufflated administration is ineffective. TS

What dose are you on? (self-reported, unverified)
Read this first. These numbers come from anonymous visitors typing in a box. Nobody checks them. People misjudge, mistype, troll, or take untested products of unknown strength. They are not a dose guide and never override the sourced table above. They exist only so the sourced ranges can be compared with what people say they take. If you are deciding what to take, use the sourced table, start low, and read the risks section.
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Duration

Route · sourceOnsetCome-upPeakOffsetTotalAfter-effects
Oral · PsychonautWiki15–30 minutes PW30–45 minutes PW1–2 hours PW2–3 hours PW4–6 hours PW–

TripSit factsheet

Onset
Oral_ER: 60-120 minutes · Oral_IR: 20-40 minutes TS
Duration
Oral_ER: 5-8 hours · Oral_IR: 3-5 hours TS
Aftereffects
1-12 hours TS

Mixing

For best safety practice, don't mix this drug with other depressants.

Why: respiratory depression. PsychonautWiki says:

Quotes from PsychonautWiki, CC BY-SA 4.0.

Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.

Backed by medical journals

Awaiting sourcePeer-reviewed reports on acute combinations, from PubMed and the journals the harm reduction sites cite.

PsychonautWiki also lists dangerous combinations shared across a whole group (opioids, serotonin syndrome) in a table this page does not copy. Read that list on PsychonautWiki.

TripSit combination chart

TripSit rates each pairing. Only pairings with a number carry a citation from TripSit. See the whole chart; TripSit's own notes are on combo.tripsit.me.

Dangerous

alcohol TScocaine TSdextromethorphan TSketamine TSmxe TStramadol TS

Caution

nitrous TSpcp TS

Low Risk & Synergy

cannabis TS

Low Risk & No Synergy

amt TScaffeine TSdmt TSlsd TSmdma TSmescaline TSmushrooms TS

Risks and toxicity

Tapentadol has a low toxicity relative to dose. As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss. It is also potentially lethal when mixed with depressants like alcohol or benzodiazepines and generally has a wider range of substances which it is dangerous to combine with in comparison to other opioids. Tapentadol is known to lower the seizure threshold. It should not be taken during benzodiazepine withdrawals as this can potentially cause seizures. PW

It is strongly recommended that one use harm reduction practices when using this drug. PW

Tolerance and addiction potential

As with other opioids, the chronic use of tapentadol can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal symptoms may occur if a person suddenly stops their usage. PW

Tolerance to many of the effects of tapentadol develops with prolonged and repeated use. The rate at which this occurs develops at different rates for different effects, with tolerance to the constipation-inducing effects developing particularly slowly for instance. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). Tapentadol presents cross-tolerance with all other opioids, meaning that after the consumption of tapentadol all opioids will have a reduced effect. PW

TripSit factsheet

Avoid
All other CNS depressants TS

Median lethal dose (LD50) in animals

Quoted from PubChem's Non-Human Toxicity Values, which come from the Hazardous Substances Data Bank (HSDB). PubChem describes them as: “Quantitative non-human toxicity values (e.g., lethal dose) for this compound. The data shown here are mostly for lab animals (e.g., rat, mouse, guinea pig, and rabbit).” and defines the “LD50 (median lethal dose, the estimated amount of a chemical expected to kill 50% of test animals in a single dose)”. PC

LD50 (as the source gives it)Reference
LD50 Rat iv 40 mg/kg PCHealth Canada; Product Monograph for Nucynta Extended-Release (Tapentadol), Drug Identification Number (DIN): 02415577 p.37 (Date of Revision: August 5, 2014). Available from, as of March 25, 2016: https://webprod5.hc-sc.gc.ca/dpd-bdpp/start-debuter.do?lang=eng (via HSDB record 8309)
LD50 Mouse po > 300 mg/kg PCHealth Canada; Product Monograph for Nucynta Extended-Release (Tapentadol), Drug Identification Number (DIN): 02415577 p.37 (Date of Revision: August 5, 2014). Available from, as of March 25, 2016: https://webprod5.hc-sc.gc.ca/dpd-bdpp/start-debuter.do?lang=eng (via HSDB record 8309)

Testing

Awaiting sourceReagent reactions and test kit guidance from a harm reduction testing service.

Effects

EuphoriaDry MouthMood liftItchinessRelaxantConstipationPupil constrictionAnalgesia TS

Overview

Tapentadol often sold under the brand name Nucynta is a synthetic opioid analgesic similar in structure to tramadol. Tapentadol has a duel mechanism of action, working on both the μ-opioid receptor and also acting as a norepinephrine reuptake inhibitor. Tapentadol is used in the management of moderate to severe pain. The subjective effects of tapentadol are similar to those of tramadol. Many users report extreme pain when trying to insufflate tapentadol. PW

An opioid analgesic drug with potency somewhere between tramadol and morphine, and with a similar action to Tramadol. Also an adrenergic reuptake inhibitor. High addiction potential. Potential for respiratory depression in overdose. Should not be combined with depressants or stimulants. TS

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.[1–5] WP

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 tapendatol with serotonergic drugs can heighten the risk of excessive serotonin accumulation while concurrent use with CNS depressants — alcohol, benzodiazepines, other opioids — can heighten the risk of profound sedation, dangerously slowed breathing, and death.[3][4][6][7][8] WP

Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours. Tapentadol is taken by mouth, and is available in immediate-release and controlled-release formulations. Tapentadol's combined mechanism of action is often compared to that of tramadol. Unlike tramadol, tapentadol is not metabolised by cytochrome P450 enzymes, but rather through glucuronidation. Due to this, tapentadol has fewer interactions with other medications and fewer side effects when compared with tramadol.[9][10][11] WP

Like tramadol, tapentadol affects both the opioid system and the norepinephrine system to relieve pain. Unlike tramadol, it has only weak effects on the reuptake of serotonin and is a significantly more potent opioid with no known active metabolites. The potency of tapentadol is somewhere between that of tramadol and morphine, with an analgesic efficacy comparable to that of oxycodone despite a lower incidence of side effects. The CDC Opioid Guidelines Calculator estimates a conversion rate of 50mg of tapentadol equaling 10 mg of oral oxycodone in terms of opioid receptor activation.[1][9][12–15] WP

In the late 1980s, Grünenthal developed tapentadol to improve on tramadol, which they had created in 1962. Their goal was to design a molecule that minimized serotonin activity, strongly activated the μ-opioid receptor, inhibited norepinephrine reuptake, and worked without metabolic activation. The result was tapentadol. Due to the high risk of addiction, substance misuse, and dependence, tapentadol is a Schedule II controlled substance in the United States, a Schedule 8 controlled drug in Australia, and a Class A controlled substance in the United Kingdom.[5][8][16–21] WP

History

History

Tapentadol was invented at the German pharmaceutical company Grünenthal in the late 1980s led by Helmut Buschmann; the team started by analyzing the chemistry and activity of tramadol, which had been invented at the same company in 1962.[16][17] WP

Tramadol has several enantiomers, and each forms metabolites after processing in the liver. These tramadol variants have varying activities at the μ-opioid receptor, the norepinephrine transporter, and the serotonin transporter, and differing half-lives, with the metabolites having the best activity. Using tramadol as a starting point, the team aimed to discover a single molecule that minimized the serotonin activity, had strong μ-opioid receptor agonism and strong norepinephrine reuptake inhibition, and would not require metabolism to be active; the result was tapentadol.[16] WP

In 2003 Grünenthal partnered with two Johnson & Johnson subsidiaries, Johnson & Johnson Pharmaceutical Research and Development and Ortho-McNeil Pharmaceutical to develop and market tapentadol; Johnson & Johnson had exclusive rights to sell the drug in the US, Canada, and Japan while Grünenthal retained rights elsewhere. In 2008 tapentadol received approval by the US Food and Drug Administration; in 2009 it was classified by US Drug Enforcement Agency as a Schedule II drug, and entered the US market. Tapentadol was reported to be the "first new molecular entity of oral centrally acting analgesics" class approved in the United States in more than 25 years.[22][23] WP

In 2010 Grünenthal granted Johnson & Johnson the right to market tapentadol in about 80 additional countries. Later that year, tapentadol was approved in Europe. In 2011, Nucynta ER, an extended release formulation of tapentadol, was released in the United States for management of moderate to severe chronic pain and received Food and Drug Administration approval the following year for the treatment of neuropathic pain associated with diabetic peripheral neuropathy.[19][24][25][26] WP

After annual sales of $166 million, in January 2015, Johnson & Johnson sold its rights to market tapentadol in the US to Depomed for $1 billion. The drug was manufactured at a plant located on the island of Puerto Rico that was hit by Hurricane Maria in 2017 causing a major shortage in the drug's availability. In January 2018 Depomed sold off the manufacturing of the drug and licensed it to Collegium Pharmaceutical for $10 million up front with an annual royalty payment of a minimum $135 million for the next 4 years. This combination of events has caused additional short supply of the drug leaving patients who depend on it to seek alternative treatments.[27][28][29] WP

Pharmacology

Pharmacodynamics

Tapentadol is a synthetic opioid with a dual mechanism of action: it acts as a full agonist of the μ-opioid receptor (MOR) and as a norepinephrine reuptake inhibitor (NRI). This unique pharmacological profile allows it to treat both nociceptive and neuropathic pain, and it is theorised that the effects on norepinephrine are a substantial benefit for people taking it. Tapentadol does not affect serotonin, unlike tramadol, which prevents the reuptake of serotonin and norepinephrine, similarly to certain antidepressants known as serotonin–norepinephrine reuptake inhibitors (SNRIs), such as desvenlafaxine and duloxetine.[33][34][35] WP

Tapentadol exhibits high binding selectivity and affinity for MOR, which is the principal target of the endogenous neuropeptide β-endorphin. It has significantly lower affinity for the δ-opioid receptor (DOR), κ-opioid receptor (KOR) and M1 as an antimuscarinic effect.[11][36][37] WP

MOR binding sites are distributed throughout the human brain, with higher densities in regions such as the amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and select cortical areas.[38] WP

Opioids like tapentadol are believed to mediate analgesia primarily through MOR activation in the midbrain periaqueductal gray (PAG) and rostral ventromedial medulla (RVM), thereby inhibiting ascending pain pathways. MOR activation in the intestine contributes to common opioid-related side effects such as constipation.[39][40] WP

As noted, tapentadol is structurally similar to tramadol, and both drugs utilize a dual mechanism involving the opioid and norepinephrine systems. However, unlike tramadol, tapentadol exerts minimal influence on serotonin reuptake and is approximately 2–3 times more potent as an opioid. Tapentadol also lacks active metabolites, which distinguishes it from tramadol and may contribute to a more predictable pharmacokinetic profile.[39][41] WP

Pharmacokinetics

Following oral administration, tapentadol typically provides onset of analgesia within 32 minutes, with effects lasting approximately 4 to 6 hours. Approximately 32% of an oral dose of tapentadol escapes first-pass metabolism in the liver, entering systemic circulation to exert pharmacological effects on both the central nervous system (CNS) and peripheral nervous system (PNS).[1][6][9][42][43] WP

The free base conversion factor for tapentadol hydrochloride is 0.86. Food intake has a minor impact on the drug's peak plasma concentration: increasing it by approximately 8% for immediate-release (IR) and 18% for extended-release (ER) formulations. These differences are not clinically significant, and tapentadol may be taken with or without food.[9][44][45] WP

Tapentadol displays dose-dependent plasma concentrations; however, higher doses (e.g., 250 mg) may produce disproportionately elevated Cmax values relative to lower doses, suggesting non-linear pharmacokinetics at higher concentrations.[46] WP

In receptor binding studies, tapentadol demonstrated a Ki of 60 nM for cloned human μ-opioid receptors, with strong agonist activity comparable to morphine, as measured by [35S]GTPγS binding assays. Its inhibitory effect on norepinephrine reuptake (Ki = 480 nM) complements its opioid activity, while its weak serotonergic effects distinguish it from dual-acting agents like tramadol. In vitro studies using human tissue indicate that tapentadol has approximately one-third the binding affinity of morphine for the human μ-opioid receptor, reflecting its comparatively lower opioid potency. Nonetheless, it retains clinically meaningful opioid activity, contributing to its analgesic effects.[1][47–50] WP

Commercial formulations contain only the (R,R)-stereoisomer. Drugs with high MOR affinity, such as tapentadol, carry an abuse potential comparable to other strong opioids like morphine, oxycodone, and hydromorphone.[51] WP

Chemistry

Formula
C14H23NO PC
CAS number
175591-23-8 PC
Molar mass (g/mol)
221.34 PC
IUPAC name (computed by PubChem)
3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol PC
SMILES
CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C PC
InChIKey
KWTWDQCKEHXFFR-SMDDNHRTSA-N PC
PubChem CID
9838022

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References

  1. Journal / agency Smit JW, Oh C, Rengelshausen J, Terlinden R, Ravenstijn PG, Wang SS, Upmalis D, Mangold B. Effects of acetaminophen, naproxen, and acetylsalicylic acid on tapentadol pharmacokinetics: results of two randomized, open-label, crossover, drug-drug interaction studies. Pharmacotherapy. January 2010. doi:10.1592/phco.30.1.25 · PMID 20030470 · PMC2888545
  2. Other Tapentadol Consumer Medicine Information. September 2020
  3. Other Tapentadol. 23 October 2024
  4. Journal / agency Khaja M, Lominadze G, Millerman K. Cardiac Arrest Following Drug Abuse with Intravenous Tapentadol: Case Report and Literature Review. The American Journal of Case Reports. July 2017. doi:10.12659/AJCR.904695 · PMID 28729524 · PMC5536129
  5. Journal / agency Drug Enforcement Agency (US). Label: Nucynta - Tapentadol hydrochloride tablet, film coated. 2019-09-18
  6. Journal / agency Alshehri FS. Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Design, Development and Therapy. 2023-03-01. doi:10.2147/dddt.s402362 · PMID 36974332 · PMC10039632
  7. Journal / agency Nucynta 50 mg
  8. Journal / agency Dart RC, Bartelson BB, Adams EH. Nonmedical use of tapentadol immediate release by college students. The Clinical Journal of Pain. August 2014. doi:10.1097/AJP.0000000000000001 · PMID 24042351
  9. Journal / agency Singh DR, Nag K, Shetti AN, Krishnaveni N. Tapentadol hydrochloride: A novel analgesic. Saudi Journal of Anaesthesia. July 2013. doi:10.4103/1658-354X.115319 · PMID 24015138 · PMC3757808
  10. Journal / agency Etropolski MS, Okamoto A, Shapiro DY, Rauschkolb C. Dose conversion between tapentadol immediate and extended release for low back pain. Pain Physician. 2010. doi:10.36076/ppj.2010/13/61 · PMID 20119464
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  15. Journal / agency CDC Opioid Calculator. 13 October 2022
  16. Other Buschmann H. Analogue-based Drug Discovery. 2013
  17. Other 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
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  19. Other Nucynta History
  20. Other Schedule 8 Medicines. 2024
  21. Other List of most commonly encountered drugs currently controlled under the misuse of drugs legislation
  22. Other Froicu D, Sinatra RS. The Essence of Analgesia and Analgesics. 2010
  23. Other Grünenthal GmbH Presents Tapentadol, a Novel Centrally Acting Analgesic, at the 25th Annual Scientific Meeting of The American Pain Society. 6 June 2006
  24. Other Janssen Pharmaceutica N.V. Announces Expansion of Licensing Agreement for Tapentadol. 7 June 2010
  25. Other Dutton G. Pain Management Market Ripe with Immediate Opportunities. 1 June 2012
  26. Other FDA Approves Nucynta ER (tapentadol) Extended-Release Oral Tablets for the Management of Neuropathic Pain Associated With Diabetic Peripheral Neuropathy
  27. Other Staff. Depomed pays over $1 billion for US rights to Janssen's Nucynta franchise. 16 January 2015
  28. Other Byrne M, Pallaria F. Dealing with Prescription Drug Shortages
  29. Other Troubled Depomed sells off Nucynta, axes 40% of workforce to pare down costs. 5 December 2017
  30. Other Anlage III BtMG - Einzelnorm
  31. Other Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien
  32. Other DEA Controlled Substances
  33. Journal / agency Schröder W, Tzschentke TM, Terlinden R, De Vry J, Jahnel U, Christoph T, Tallarida RJ. Synergistic interaction between the two mechanisms of action of tapentadol in analgesia. The Journal of Pharmacology and Experimental Therapeutics. April 2011. doi:10.1124/jpet.110.175042 · PMID 21262850 · PMC3364495
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  48. Journal / agency Tapentadol
  49. Journal / agency Wiffen PJ, Derry S, Naessens K, Bell RF. Oral tapentadol for cancer pain. The Cochrane Database of Systematic Reviews. September 2015. doi:10.1002/14651858.CD011460.pub2 · PMID 26403220 · PMC6483480
  50. Other Tapentadol use and harms in Australia: Analysis of opioid sales data and sentinel survey data from people who inject drugs. 2020-06-23
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Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.