Tapentadol Hydrochloride

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Cat Number

API0232152

CAS Number

175591-09-0

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Product Detail Description Scientific Support Customer Q&A

CAS Number

175591-09-0

EINECS

687-970-4

Storage

Store at room temperature

Synonyms

Tapentadol HCl; Nucynta; Palexia; Nucynta ER; BN-200 HYDROCHLORIDE; 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol hydrochloride

Molecular Formula

C14H24ClNO

Molecular Weight

257.8

Smiles

CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C.Cl

Melting Point

209-210°C

Boiling Point

323.493°C at 760 mmHg

General Description

Tapentadol hydrochloride is a centrally acting analgesic with a novel dual mechanism: mu‑opioid receptor agonism and norepinephrine reuptake inhibition (NRI). Its chemical structure is a 3‑(3‑dimethylamino‑1‑ethyl‑2‑methylpropyl)phenol, unrelated to classical opioids or SNRIs. The hydrochloride salt enhances solubility. The molecule has two chiral centers; the pharmaceutical is a single enantiomer.

Mechanism of Action

Tapentadol acts as a full agonist at the mu‑opioid receptor with approximately 1/50 the potency of morphine, and also inhibits the presynaptic reuptake of norepinephrine via the norepinephrine transporter (NET). The dual mechanism produces synergistic analgesia in both ascending and descending pain pathways. Unlike pure opioids, tapentadol has a ceiling effect for respiratory depression and less μ‑receptor‑mediated gastrointestinal effects.

Application

Tapentadol is indicated for the management of moderate to severe acute pain (immediate‑release) and for chronic pain (extended‑release) when continuous opioid analgesia is required. It is also approved for diabetic peripheral neuropathy (DPN). The norepinephrine component contributes to efficacy in neuropathic pain, and the reduced μ‑receptor load results in lower rates of nausea, vomiting, and constipation compared to equianalgesic doses of oxycodone.

Two open‑label trials (57 children from birth to <2 years, including 8 preterm neonates) assessed single doses of tapentadol oral solution or intravenous infusion; a third double‑blind placebo‑controlled trial (15 patients) assessed multiple oral doses after surgery. Tapentadol serum concentrations fell within the adult target range, and pain improved within 15 minutes. In the multiple‑dose trial, supplemental opioid use was low, and all patients stopped treatment because pain resolved. Treatment‑emergent adverse events were mild and none serious. Tapentadol shows favorable pharmacokinetics, efficacy, and safety in children under 2 years of age.

Fig. 1 Dose finding process for tapentadol oral solution and intravenous infusion for the age range preterm neonates to children <18 years of age. (Eissa A, et al., 2021)

References

Eissa A, et al. Tapentadol for the Treatment of Moderate-to-Severe Acute Pain in Children Under the Age of Two Years. J Pain Res. 2021;14:229-248.

Does Tapentadol Hydrochloride require protection from light during long-term storage?

Yes, it is moderately photosensitive. Prolonged light exposure can cause discoloration and degradation. Store in light-resistant containers.

What is the recommended storage temperature for Tapentadol Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate racemization and formation of phenolic impurities.

Is Tapentadol Hydrochloride hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity tapentadol N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.