Dimethocaine
[CAS# 94-15-5]

Identification

• Classification: API >> Other chemicals
• Name: Dimethocaine
• Synonyms: 3-Diethylamino-2,2-dimethylpropyl 4-aminobenzoate; 4-Aminobenzoic acid 3-(diethylamino)-2,2-dimethylpropyl ester; Larocaine; NSC 68927
• Molecular Formula: C₁₆H₂₆N₂O₂
• Molecular Weight: 278.39
• CAS Registry Number: 94-15-5
• SMILES: CCN(CC)CC(C)(C)COC(=O)C1=CC=C(C=C1)N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 1.035 g/cm³
• Index of Refraction: 1.529, Calc.^*
• Boiling Point: 403.5±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 197.8±23.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Dimethocaine, also known as larocaine, is a synthetic local anesthetic derived from the cocaine structure. The compound was first synthesized in the early 20th century as part of a broader effort to develop safer and more effective alternatives to cocaine for medical and dental applications. Its discovery was aimed at mitigating the side effects and addictive properties associated with cocaine use, while retaining the desirable anesthetic effects.

Chemically, dimethocaine is classified as an ester of p-aminobenzoic acid and diethylamine. Its structure features a methoxy group, which distinguishes it from other local anesthetics and contributes to its unique pharmacological properties. The synthesis of dimethocaine involves the reaction of cocaine or its derivatives with diethylamine, followed by various purification processes to yield the final product.

Dimethocaine exhibits local anesthetic properties similar to those of cocaine, but with a more favorable safety profile. Its primary application is in the field of medicine, where it is used for topical anesthesia in various surgical and dental procedures. Due to its ability to block nerve conduction, dimethocaine effectively numbs targeted areas, allowing for pain-free interventions. This makes it a valuable tool for healthcare professionals in both clinical and outpatient settings.

In addition to its medical applications, dimethocaine has gained attention in the field of recreational drug use. Its euphoric effects, similar to those of cocaine, have led to its misuse and popularity as a recreational stimulant. This duality of use has raised concerns regarding its potential for abuse, prompting regulatory scrutiny in various countries. Despite its legal status varying by region, the recreational use of dimethocaine highlights the ongoing challenge of balancing the therapeutic benefits of chemical substances with their potential for misuse.

Dimethocaine's applications extend beyond medicine and recreation, as it has also been studied for its potential use in veterinary medicine. Its efficacy as a local anesthetic in animals presents opportunities for improving pain management in veterinary procedures. Research in this area is ongoing, focusing on optimizing dosing regimens and assessing safety profiles for different animal species.

Safety considerations are crucial when using dimethocaine, as with any local anesthetic. Adverse effects can include allergic reactions, cardiovascular complications, and central nervous system toxicity if not used appropriately. Therefore, it is essential for practitioners to adhere to established guidelines and monitor patients closely during and after administration.

In conclusion, dimethocaine is a synthetic local anesthetic with a rich history of discovery and diverse applications in medicine, veterinary care, and recreational use. Its ability to provide effective local anesthesia while minimizing the risks associated with cocaine has established it as a significant compound in clinical practice. Ongoing research continues to explore its potential applications and ensure safe usage.

References

2014. Dimethocaine, a synthetic cocaine derivative: Studies on its in vitro metabolism catalyzed by P450s and NAT2. Toxicology Letters, 225(1).
DOI: 10.1016/j.toxlet.2013.11.033

2014. Dimethocaine, a synthetic cocaine analogue: studies on its in-vivo metabolism and its detectability in urine by means of a rat model and liquid chromatography-linear ion-trap (high-resolution) mass spectrometry. Analytical and Bioanalytical Chemistry, 406(7).
DOI: 10.1007/s00216-013-7539-0

1996. Stimulant activities of dimethocaine in mice: reinforcing and anxiogenic effects. Psychopharmacology, 127(4).
DOI: 10.1007/bf02806010