Dibucaine Hydrochloride

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Cat Number

API61121

CAS Number

61-12-1

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CAS Number

61-12-1

EINECS

200-498-1

Storage

2-8℃

Synonyms

2-butoxy-n-(2-(diethylamino)ethyl)-cinchoninamidmonohydrochloride

Molecular Formula

C20H30ClN3O2

Molecular Weight

379.9

Smiles

CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC.Cl

Appearance

Solid

Melting Point

99-101℃

Relative Density

1.13

General Description

Dibucaine Hydrochloride is the hydrochloride salt of dibucaine (cinchocaine), one of the most potent and longest-acting amide-type local anesthetics. Its quinoline-based structure, featuring a dibutylaminoethylamino-quinoline-4-carboxamide scaffold, is unique among amide local anesthetics.

Mechanism of Action

Dibucaine Hydrochloride blocks voltage-gated sodium channels with high affinity due to its large lipophilic quinoline ring system, preventing membrane depolarization and nerve impulse conduction. Its high lipophilicity results in deep penetration into nerve membranes and prolonged sodium channel occupation.

Application

Used as a topical local anesthetic for mucous membrane anesthesia and as a spinal anesthetic. Dibucaine Hydrochloride is one of the most potent and longest-acting amide local anesthetics, with a unique quinoline-based structure providing deep, prolonged anesthesia. It also serves as the diagnostic agent for pseudocholinesterase deficiency testing.

The interaction between Dibucaine hydrochloride and a sodium channel inactivation gate peptide (MP-1A, Ac-GGQDIFMTEEQK-NH2) derived from the cytoplasmic linker between domains III and IV of the rat brain type IIA sodium channel alpha-subunit (G1484-K1495) was investigated by 1H-NMR spectroscopy. Changes in the 1H-NMR chemical shifts of the aromatic proton resonances of dibucaine at pH 7.0 in phosphatidylserine suspensions were observed.
To elucidate the molecular mechanism, several peptide mutants were examined including substitution of glutamine for phenylalanine (F1489Q; MP-2A), substitution of D-phenylalanine for L-phenylalanine (MP-1A'), and substitution of neutral amino acid residues for acidic residues (D1487N, MP-1NA; E1492Q, MP-IQEA; E1493Q, MP-IEQA). The results led to three conclusions. First, the aromatic ring of phenylalanine at position 1489 of MP-1A interacts with the quinoline ring of dibucaine through pi-pi stacking. Second, the tertiary amine nitrogen of dibucaine interacts electrostatically with the aspartic acid residue at position 1487 (D1487). Third, the presence of phosphatidylserine lipids reinforces these molecular interactions.

Fig. 1 Changes in chemical shifts of the quinoline ring proton resonances of Dibucaine as caused by the peptides. (KURODA Y.; et al. 2000)

References

KURODA Y, et al. Interactions between local anesthetics and Na+ channel inactivation gate peptides in phosphatidylserine suspensions as studied by 1H-NMR spectroscopy. Chemical and pharmaceutical bulletin, 2000, 48(9): 1293-1298.

Dibucaine hydrochloride was identified as an effective inhibitor of ketoprofen photodegradation induced by UV irradiation, which follows first-order reaction kinetics and yields three photoproducts. While antioxidants inhibit photodegradation through free radical scavenging, dibucaine demonstrated a different mechanism of action. The local anesthetic effectively suppressed the formation of photoproducts and reduced the rate of ketoprofen degradation under UV exposure. This study revealed a previously unrecognized photostabilizing property of dibucaine hydrochloride, distinct from conventional antioxidant pathways, suggesting potential applications in formulating photolabile drugs to prevent UV-induced degradation.

Fig. 2 Photostabilizing property of Dibucaine Hydrochloride. (Takara A.; et al. 2017)

References

Takara A, et al. Dibucaine inhibits ketoprofen photodegradation via a mechanism different from that of antioxidants. Journal of Photochemistry and Photobiology A: Chemistry, 2017, 333: 208-212.

What makes Dibucaine useful for pseudocholinesterase deficiency testing?

Dibucaine inhibits normal pseudocholinesterase by approximately 80% but atypical variants by only 20-30%, making it the standard diagnostic reagent for identifying patients at risk for prolonged neuromuscular blockade.

What storage conditions are required?

Should be stored at 2-8℃ in a tightly sealed container, protected from light and moisture.

What purity grade is available?

Supplied as a high-purity grade suitable for R&D and pharmaceutical manufacturing.

Can packaging be customized?

Order quantities and packaging formats are customizable upon request for R&D and production needs.