Fentanyl Hydrochloride

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Cat Number

API0232116

CAS Number

1443-54-5

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CAS Number

1443-54-5

EINECS

685-598-7

Storage

Store at room temperature

Synonyms

Fentanyl HCl; IONSYS; UNII-59H156XY46; N-(1-Phenethyl-4-piperidyl)propionanilide hydrochloride; 59H156XY46; DTXSID90162666

Molecular Formula

C22H29ClN2O

Molecular Weight

372.9

Smiles

CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.Cl

Appearance

White crystals or powder

Melting Point

87.5°C

Boiling Point

466°C

Relative Density

1.1

General Description

Fentanyl hydrochloride is a synthetic piperidine-derived opioid analgesic, structurally related to meperidine but 50 to 100 times more potent than morphine. Its chemical name is N-(1-phenethyl-4-piperidinyl)-N-phenylpropanamide, with a lipophilic structure that facilitates rapid penetration of the blood-brain barrier. The hydrochloride salt provides water solubility for parenteral use. The molecule has a piperidine ring, a phenethyl group, and a propanamide side chain, contributing to its high mu-receptor affinity.

Mechanism of Action

Fentanyl is a highly selective full agonist at the mu-opioid receptor (MOR), activating G-protein-coupled signaling that inhibits adenylate cyclase and reduces neuronal excitability. This leads to decreased neurotransmitter release (including substance P, GABA, and glutamate) in pain pathways. The drug produces profound analgesia, euphoria, respiratory depression, and physical dependence. Its high lipophilicity allows rapid onset and redistribution, but the effect is terminated by tissue redistribution rather than metabolism.

Application

Fentanyl is indicated for the management of severe acute pain (e.g., surgical anesthesia, postoperative pain) and for breakthrough pain in cancer patients tolerant to other opioids. It is also used as a general anesthetic adjunct. Due to its high potency and rapid onset, fentanyl is a common agent for procedural sedation. Transdermal formulations are used for chronic pain, exploiting its high lipophilicity.

A meta‑analysis of 11 studies (965 lidocaine‑treated, 745 controls) assessed prophylactic intravenous lidocaine for preventing fentanyl‑induced cough (FIC). Lidocaine significantly reduced the incidence of FIC compared with placebo (OR 0.27, 95% CI 0.21‑0.35), with consistent effects in both adults and children. Both low (0.5‑1.0 mg/kg) and high (1.5‑2.0 mg/kg) doses were effective, with no significant difference between them. Fentanyl dose did not contribute to heterogeneity. Prophylactic IV lidocaine effectively prevents FIC across a range of doses.

Fig. 1 Funnel plots for the effects of lidocaine on FIC. (Tan W, et al., 2018)

References

Tan W, et al. Prophylactic Intravenous Lidocaine at Different Doses for Fentanyl-Induced Cough (FIC): A Meta-Analysis. Sci Rep. 2018;8(1):9946.

A scoping review of 64 genetic association studies examined CYP3A4 and CYP3A5 variants in relation to fentanyl overdose risk. The no‑function CYP3A5*3 (rs776746) allele was consistently associated with increased overdose risk, particularly supported by pharmacokinetic studies. Evidence for CYP3A4 variants (e.g., rs2242480) was less robust. The authors recommend prospective genotyping of at‑risk populations, integration of pharmacogenetics with psychiatric genetics, and large‑scale data harmonization to improve risk prediction.

Fig. 2 Simplified theoretical schema of causal associations between fentanyl overdose, pharmacokinetics, risk factors for exposure, genetics, and ancestry, race, and ethnicity. (Petrovitch D, et al., 2025)

References

Petrovitch D, et al. Scoping review of associations between cytochrome P450 3A4/5 single nucleotide polymorphisms and risk factors for fentanyl overdose. Pharmacogenomics. 2025;26(10-12):391-425.

What are the security requirements for shipping Fentanyl Hydrochloride as a potent opioid?

As a Schedule II controlled substance, shipments require secure, chain-of-custody protocols with tamper-evident packaging.

What is the recommended storage temperature for Fentanyl Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidative degradation of the piperidine ring.

Is Fentanyl Hydrochloride sensitive to light and moisture?

It is moderately photosensitive and slightly hygroscopic. Store in light-resistant, tightly sealed containers with desiccant to maintain purity.

How is the impurity norfentanyl (a major metabolite and degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method with highly sensitive detection, ensuring it remains within ICH limits.