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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).[6] Tapentadol is used medically for the treatment of moderate to severe pain.[2] It is highly addictive and is a commonly abused drug.[2][8][9][10]
Frequently reported adverse effects include euphoria, constipation, nausea, vomiting, headaches, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating.[11] More severe adverse reactions can occur, including addiction and dependence, substance abuse, respiratory depression, and an elevated risk of serotonin syndrome.[12][13] 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.[9][14]
Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours.[15] Tapentadol is taken by mouth, and is available in immediate-release and controlled-release formulations.[16] Tapentadol’s combined mechanism of action is often compared to that of tramadol.[15] Unlike tramadol, tapentadol is not metabolised by cytochrome P450 enzymes, but rather through glucuronidation.[17] Due to this, tapentadol has fewer interactions with other medications and fewer side effects when compared with tramadol.[17]
Like tramadol, tapentadol affects both the opioid system and the norepinephrine system to relieve pain.[18] Unlike tramadol, it has only weak effects on the reuptake of serotonin and is a significantly more potent opioid with no known active metabolites.[15][19] The potency of tapentadol is somewhere between that of tramadol and morphine,[20] with an analgesic efficacy comparable to that of oxycodone despite a lower incidence of side effects.[6] The CDC Opioid Guidelines Calculator estimates a conversation rate of 50mg of tapentadol equaling 10 mg of oral oxycodone in terms of opioid receptor activation.[21]
In the late 1980s, Grünenthal developed tapentadol to improve on tramadol,[22] which they had created in 1962.[23] 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.[22] The result was tapentadol. Due to the high risk of addiction, substance misuse, and dependence,[24][10][14] tapentadol is a Schedule II controlled substance in the United States,[25] a Schedule 8 controlled drug in Australia,[26] and a Class A controlled substance in the United Kingdom.[27]
Medical use
Tapentadol is used for the treatment of moderate to severe pain for both acute (following e.g. injury or surgery) and chronic musculoskeletal pain.[28] It is also specifically indicated for controlling the pain of diabetic neuropathy when around-the-clock opioid medication is required.
Extended-release formulations of tapentadol are not indicated for use in the management of acute pain and are instead indicated only for the relief of severe, disabling pain, that is long-term in nature and cannot be controlled by any other pharmacological means.[6][29][30]
Tapentadol is pregnancy category C. There are no adequate and well-controlled studies of tapentadol in pregnant women, and tapentadol is not recommended for use in women during and immediately prior to labor and delivery.[30]
There are no adequate and well-controlled studies of tapentadol in children.
Specification
The Tapentadol with CAS registry number of 175591-23-8 is also known as Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-. The IUPAC name is 3-[(2R,3R)-1-(Dimethylamino)-2-methylpentan-3-yl]phenol. In addition, the formula is C14H23NO and the molecular weight is 221.34. This chemical is a centrally acting analgesic with a dual mode of action as an agonist at the μ-opioid receptor and as a norepinephrine reuptake inhibitor.
Physical properties about Tapentadol are: (1)ACD/LogP: 3.02; (2)ACD/LogD (pH 7.4): 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 2; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 13; (7)#H bond acceptors: 2; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 6; (10)Index of Refraction: 1.518; (11)Molar Refractivity: 69.164 cm3; (12)Molar Volume: 228.099 cm3; (13)Surface Tension: 36.154 dyne/cm; (14)Density: 0.97 g/cm3; (15)Flash Point: 134.18 °C; (16)Enthalpy of Vaporization: 58.792 kJ/mol; (17)Boiling Point: 323.493 °C at 760 mmHg.
Tapentadol Product Information
Tapentadol is listed under API and is intended for research and analytical applications. It is associated with Tapentadol. This is a controlled substance entry for enquiry only. Any possible supply discussion is subject to due diligence, certification, permits, documentation, intended end-use and applicable compliance review.
This controlled substance entry is shown for qualified research enquiry and compliance review, with product information including CAS number, molecular formula, molecular weight and enquiry details.
Technical Data
Description
Tapentadol
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Researchers and formulators face unpredictable analgesic efficacy with prodrug opioids like tramadol, which rely on CYP2D6 metabolism. Tapentadol provides a direct-acting dual MOR agonist/NRI, eliminating genotype-driven variability. • Direct MOR agonism & NRI; no metabolic activation needed, bypassing CYP2D6 polymorphism. • Tapentadol HCl aqueous solubility 380 mg/mL, log P 2.89, ideal for high-loading IR/ER matrices. • 24% lower nausea/vomiting vs equianalgesic oxycodone, enabling better-tolerated analgesics.
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Tapentadol (CAS 175591-23-8) and its highly processable hydrochloride salt (CAS 175591-09-0) represent a distinct class of centrally acting analgesics characterized by a dual mechanism of action: µ-opioid receptor (MOR) agonism and norepinephrine reuptake inhibition (NRI). Unlike traditional opioids, tapentadol is engineered to balance these two mechanisms within a single molecule, providing robust efficacy while minimizing classical opioid-related adverse effects. From a formulation and procurement standpoint, tapentadol hydrochloride offers excellent physicochemical properties, including a high aqueous solubility of 380 mg/mL and a favorable partition coefficient (log P = 2.89), making it highly suitable for both immediate-release (IR) and extended-release (ER) aqueous matrix manufacturing [1].
Research Fit
While tramadol is frequently considered a structural and functional in-class comparator, substituting tapentadol with tramadol introduces critical pharmacokinetic liabilities. Tramadol is a prodrug that relies heavily on cytochrome P450 2D6 (CYP2D6) metabolism to convert into its active M1 metabolite (O-desmethyltramadol) to achieve meaningful MOR agonism. This dependence results in high inter-patient variability, rendering the drug ineffective in the ~6% of the population who are CYP2D6 poor metabolizers, while posing toxicity risks to ultra-rapid metabolizers[1]. In contrast, tapentadol is a direct-acting molecule that requires no metabolic activation and is primarily cleared via Phase II glucuronidation [2]. For pharmaceutical developers and procurement teams, selecting tapentadol eliminates genotype-dependent efficacy variations and mitigates the risk of CYP-mediated drug-drug interactions, ensuring a highly predictable pharmacokinetic profile.
Substitution Risk
- Tramadol—Metabolic activation via CYP2D6 introduces variability; direct MOR agonism and NRI profile may not transfer.
- Morphine / Oxycodone—Pure MOR agonists lack noradrenergic component; neuropathic pain pathway response may differ.
- Racemic or other stereoisomers—Only (R,R)-enantiomer is pharmacologically active; enantiomeric identity mismatch can alter assay outcomes.
CYP2D6-Independent Glucuronidation Pathway
Tapentadol differentiates itself from tramadol by operating entirely independent of the CYP2D6 metabolic pathway. While tramadol requires CYP2D6 activation to form its active M1 metabolite, tapentadol is a direct-acting analgesic that undergoes Phase II glucuronidation (forming the inactive tapentadol-O-glucuronide) [1]. This eliminates the efficacy failures seen in CYP2D6 poor metabolizers (approximately 6% of Caucasians) and avoids the toxicity spikes in ultra-rapid metabolizers [2].
| Evidence Dimension | Metabolic activation requirement and CYP2D6 dependence |
| Target Compound Data | Direct-acting, Phase II glucuronidation, 0% CYP2D6 dependence |
| Comparator Or Baseline | Tramadol (Prodrug, requires CYP2D6 for active M1 metabolite formation) |
| Quantified Difference | Elimination of the ~6% population variability linked to CYP2D6 deficiency |
| Conditions | Human pharmacokinetic profiling and metabolomics |
Procuring tapentadol ensures a predictable, genotype-independent therapeutic profile, which is critical for developing universally effective analgesic formulations.
MOR-NRI Receptor Binding Synergy
Tapentadol demonstrates a distinct synergistic binding profile, exhibiting a Ki value of 0.16 µM for the human recombinant µ-opioid receptor (MOR) and a Ki of 0.48 µM for the norepinephrine transporter (NET) [1]. Compared to morphine, which has a significantly higher MOR affinity (Ki = 0.002 µM), tapentadol’s MOR affinity is approximately 50-fold lower[2]. However, the concurrent NRI activity provides an opioid-sparing effect, allowing tapentadol to achieve equianalgesic in vivo efficacy to strong opioids but with a reduced opioid receptor burden.
| Evidence Dimension | µ-opioid receptor (MOR) binding affinity (Ki) |
| Target Compound Data | Ki = 0.16 µM for hMOR; Ki = 0.48 µM for NET |
| Comparator Or Baseline | Morphine (Ki = 0.002 µM for MOR) |
| Quantified Difference | 50-fold lower MOR affinity for tapentadol, yet comparable in vivo analgesic efficacy due to NRI synergy |
| Conditions | Human recombinant receptor binding assays and rat synaptosomal reuptake assays |
This dual-mechanism synergy allows formulators to achieve strong analgesic targets while structurally minimizing the severe side effects associated with high-affinity MOR agonists.
GI Tolerability vs. Oxycodone
In comparative clinical evaluations at equianalgesic doses, tapentadol immediate release (IR) demonstrates a quantitatively superior gastrointestinal tolerability profile compared to oxycodone IR. In a phase 3 study, patients receiving tapentadol IR 50 mg reported a 35% incidence of nausea and/or vomiting, whereas patients receiving oxycodone HCl IR 10 mg reported a 59% incidence [1]. This statistically significant reduction (P < 0.001) in GI adverse events highlights tapentadol’s opioid-sparing mechanism in practice.
| Evidence Dimension | Incidence of nausea and/or vomiting |
| Target Compound Data | Tapentadol IR 50 mg (35% incidence) |
| Comparator Or Baseline | Oxycodone HCl IR 10 mg (59% incidence) |
| Quantified Difference | 24% absolute reduction in GI adverse events at equianalgesic dosing |
| Conditions | Phase 3 postoperative pain clinical trial |
The significantly lower GI side effect burden makes tapentadol a preferred API for formulations targeting patients who cannot tolerate classical strong opioids.
High Aqueous Solubility for Formulations
From a manufacturing perspective, tapentadol hydrochloride possesses highly favorable physicochemical properties for formulation development. It exhibits an aqueous solubility of 380 mg/mL at ambient temperature and a partition coefficient (log P) of 2.89 in a 1-octanol/water system [1]. This classifies it as freely soluble in water, providing a distinct processing advantage over more lipophilic or poorly soluble in-class analogs, and facilitating straightforward incorporation into both immediate-release and complex extended-release hydrophilic matrix systems [2].
| Evidence Dimension | Aqueous solubility and partition coefficient |
| Target Compound Data | Solubility = 380 mg/mL; log P = 2.89 |
| Comparator Or Baseline | Baseline lipophilic opioid APIs (often requiring co-solvents or complexation) |
| Quantified Difference | Freely soluble status (380 mg/mL) enables high-dose aqueous processing without solubility enhancers |
| Conditions | Ambient temperature water solubility and 1-octanol/aqueous buffered solution 2-phase system |
High aqueous solubility streamlines the scale-up and manufacturing of advanced dosage forms, reducing formulation complexity and production costs.
Genotype-Independent Analgesics
Because tapentadol does not rely on CYP2D6 for metabolic activation, it is a highly reliable API for developing universally predictable pain management therapeutics. This is particularly relevant for global markets where CYP2D6 polymorphism (e.g., poor or ultra-rapid metabolizers) renders prodrugs like tramadol unreliable or unsafe [1].
High-Dose Aqueous & ER Formulations
The exceptional aqueous solubility of tapentadol hydrochloride (380 mg/mL) and its favorable log P (2.89) make it a highly processable candidate for high-concentration liquid formulations, injectables, and hydrophilic extended-release (ER) matrix tablets. Formulators can achieve high drug loading without the need for complex solubility enhancers or co-solvents [2].
Dual-Mechanism Neuropathic Pain Assays
In preclinical pharmacology and drug discovery, tapentadol serves as a primary reference standard for MOR-NRI (µ-opioid receptor agonist / norepinephrine reuptake inhibitor) dual-mechanism activity. Its specific binding profile (MOR Ki = 0.16 µM, NET Ki = 0.48 µM) allows researchers to benchmark novel synergistic compounds targeting neuropathic pain pathways without the confounding variable of active metabolites [3].
Low-GI-Burden Opioid Replacements
For pharmaceutical procurement teams designing therapeutics for patients sensitive to classical opioids, tapentadol offers a validated pathway to reduce gastrointestinal adverse events. Its demonstrated 24% absolute reduction in nausea and vomiting compared to equianalgesic oxycodone makes it a highly suitable active ingredient for improved-tolerability pain management portfolios [4].
Application Fit Matrix
References
- [1] Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Toxicology Mechanisms and Methods, 2016.
- [2] FDA NDA 22-304; Tapentadol HCI Environmental Assessment. U.S. Food and Drug Administration, 2008.
- [3] Review of Structural Modification and Development of Novel Tramadol Derivatives. Pharmaceuticals, 2026.
- [4] Tapentadol immediate release: a new treatment option for acute pain management. Journal of Pain Research, 2010.
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log Kow = 3.57 (est)
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GHS Hazard Statements
Reported as not meeting GHS hazard criteria by 1 of 2 companies. For more detailed information, please visit ECHA C&L website;
Of the 1 notification(s) provided by 1 of 2 companies with hazard statement code(s):;
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];
H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard];
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Use and Manufacturing
Drug Indication
Therapeutic Uses
Nucynta (tapentadol) is indicated for the relief of moderate to severe acute pain in patients 18 years of age or older. /Included in US product label/
Nucynta ER (tapentadol) is indicated for the management of: pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate; neuropathic pain associated with diabetic peripheral neuropathy (DPN) in adults severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. Limitations of Usage: Because of the risks of addiction, abuse, and misuse with opioids, even at recommended doses, and because of the greater risks of overdose and death with extended-release opioid formulations, reserve Nucynta ER for use in patients for whom alternative treatment options (e.g., non-opioid analgesics or immediate-release opioids) are ineffective, not tolerated, or would be otherwise inadequate to provide sufficient management of pain. Nucynta ER is not indicated as an as-needed (prn) analgesic. /Included in US product label/
… Tapentadol /is/ a combined mu-opioid receptor agonist and noradrenaline reuptake inhibitor … .
CDC Guideline for Prescribing Opioids for Chronic Pain – United States, 2016; This guideline provides recommendations for primary care clinicians who are prescribing opioids for chronic pain outside of active cancer treatment, palliative care, and end-of-life care. The guideline addresses 1) when to initiate or continue opioids for chronic pain; 2) opioid selection, dosage, duration, follow-up, and discontinuation; and 3) assessing risk and addressing harms of opioid use. CDC developed the guideline using the Grading of Recommendations Assessment, Development, and Evaluation (GRADE) framework, and recommendations are made on the basis of a systematic review of the scientific evidence while considering benefits and harms, values and preferences, and resource allocation. CDC obtained input from experts, stakeholders, the public, peer reviewers, and a federally chartered advisory committee. It is important that patients receive appropriate pain treatment with careful consideration of the benefits and risks of treatment options. This guideline is intended to improve communication between clinicians and patients about the risks and benefits of opioid therapy for chronic pain, improve the safety and effectiveness of pain treatment, and reduce the risks associated with long-term opioid therapy, including opioid use disorder, overdose, and death.
Pharmacology
Tapentadol is an orally available, synthetic benzenoid that acts as an agonist for the mu-opioid receptor (MOR) and inhibits the reuptake of noradrenaline, with potential anti-nociceptive activity. Upon oral administration, tapentadol binds to the MOR which enhances MOR-mediated signaling, interferes with the sensation of pain and results in an analgesic effect. Tapentadol also inhibits the reuptake of noradrenaline, which increases the levels of noradrenaline (NA), activates the inhibitory alpha-2 receptors and results in an analgesic effect.
MeSH Pharmacological Classification
ATC Code
N02 – Analgesics
N02A – Opioids
N02AX – Other opioids
N02AX06 – Tapentadol
Mechanism of Action
Treatments for neuropathic pain are either not fully effective or have problematic side effects. Combinations of drugs are often used. Tapentadol is a newer molecule that produces analgesia in various pain models through two inhibitory mechanisms, namely central mu-opioid receptor (MOR) agonism and noradrenaline reuptake inhibition. These two components interact synergistically, resulting in levels of analgesia similar to opioid analgesics such as oxycodone and morphine, but with more tolerable side effects. The right central nucleus of the amygdala (CeA) is critical for the lateral spinal ascending pain pathway, regulates descending pain pathways and is key in the emotional-affective components of pain. Few studies have investigated the pharmacology of limbic brain areas in pain models. Here we determined the actions of systemic tapentadol on right CeA neurones of animals with neuropathy and which component of tapentadol contributes to its effect. Neuronal responses to multimodal peripheral stimulation of animals with spinal nerve ligation or sham surgery were recorded before and after two doses of tapentadol. After the higher dose of tapentadol either naloxone or yohimbine were administered. Systemic tapentadol resulted in dose-dependent decrease in right CeA neuronal activity only in neuropathy. Both naloxone and yohimbine reversed this effect to an extent that was modality selective. The interactions of the components of tapentadol are not limited to the synergy between the MOR and a2-adrenoceptors seen at spinal levels, but are seen at this supraspinal site where suppression of responses may relate to the ability of the drug to alter affective components of pain.
KEGG Target based Classification of Drugs
Solute carrier family
SLC6
Tapentadol (CAS 175591-23-8) Industry Research 2025: Global and Regional Market Trends 2019-2024 and Forecast to 2029
Report- 50 Pages
- September 2026
- Region: Global
- Merchant Research and Consulting Ltd
- ID: 4185422
It explores various applications and examines manufacturing methods, supported by an analysis of relevant patents. The global market analysis covers constraints, drivers, and opportunities from 2019 to 2024, supply and demand dynamics, suppliers and regional overviews across Europe, Asia, North America, and other regions.
The report forecasts future trends and supply-demand scenarios up to 2029, with detailed market predictions by region. Additionally, it analyzes market prices across different regions and evaluates the end-use sectors for Tapentadol.
The Tapentadol global market report covers the following key points:
- Tapentadol description, applications and related patterns
- Tapentadol market drivers and challenges
- Tapentadol manufacturers and distributors
- Tapentadol prices
- Tapentadol end-users
- Tapentadol downstream industries trends
Key questions answered in the report:
- What were the main trends of the global Tapentadol market in 2019-2024?
- What was the size of the global Tapentadol market in 2019-2024?
- Who are the main players in the global Tapentadol market?
- Which drivers and challenges will determine the development of the global Tapentadol market during 2025-2029?
- What will the CAGRs be for the global product industry?
- And many others
This product will be delivered within 5-7 business days.
Table of Contents
2. TAPENTADOL APPLICATIONS3. TAPENTADOL MANUFACTURING METHODS4. TAPENTADOL PATENTS
10. TAPENTADOL END-USE SECTOR
Tapentadol 175591-23-8
| Catalogue No | PA 20 2650000 |
| CAS No |
175591-23-8 |
| Chemical Name | Tapentadol |
| Molecular Formula | C14H23NO |
| Weight | 221.34 |
| Similar Products | 175591-09-0 (HCl Salt) , 1356394-30-3 (x phosphate salt) |
| Storage | 2-8°C Refrigerator |
| Shipping Conditions | Ambient |
| Category |
Pharmaceutical Reference Standards, Intermediates, impurities, metabolites, pharmaceutical standards, Fine Chemicals |
| Appearance | NA |
| Synonyms | 3-((2R,3R)-1-(Dimethylamino)-2-methylpentan-3-yl)phenol; Nucynta; Palexia; 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol; |
A hydrochloride salt of Tapentadol, which is an opioid analgesic of the benzenoid class. It is used for the treatment of moderate to severe pain and chronic musculoskeletal pain. Also controls pain of diabetic neuropathy . An agonist of the μ-opioid receptor and a norepinephrine reuptake inhibitor (NRI)
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CAS No : 175591-23-8 | Chemical Name : Tapentadol – Pharmaffiliates
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CAS Number: 175591-23-8
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Chemical name: Tapentadol
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CAS No.175591-23-8,3- (1-dimethylamino-2-methyl-pentan-3-yl
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Tapentadol (CAS 175591-23-8) | Physicochemical properties
Detailed information about Tapentadol (CAS 175591-23-8), including physicochemical properties, SDS, safety data, applications, and …
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Tapentadol Hydrochloride | LGC Standards
Centrally acting oral analgesic with a dual mode of action that has demonstrated efficacy in preclinical and clinical models of pain relief.
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