Procaine
[CAS# 59-46-1]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: Procaine
• Synonyms: 2-(Diethylamino)ethyl 4-aminobenzoate; 4-Aminobenzoic acid 2-diethylaminoethyl ester
• Molecular Formula: C₁₃H₂₀N₂O₂
• Molecular Weight: 236.31
• CAS Registry Number: 59-46-1
• EC Number: 200-426-9
• SMILES: CCN(CC)CCOC(=O)C1=CC=C(C=C1)N

Properties

• Solubility: 5mg/mL (water), 10mM (DMSO)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 62 $deree$C
• Index of Refraction: 1.543, Calc.^*
• Boiling Point: 373.6±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 179.8±22.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Procaine is a local anesthetic with the chemical formula C13H18N2O2S. It belongs to the amino ester class of local anesthetics and is widely recognized for its application in medical and dental procedures. The discovery of procaine can be traced back to the early 20th century, specifically to 1905, when it was synthesized by the German chemist Alfred Einhorn. Einhorn was seeking to create a less toxic alternative to cocaine, which had been commonly used as a local anesthetic but posed significant health risks.

The synthesis of procaine marked a significant advancement in the field of anesthesia. Cocaine, while effective, had several drawbacks, including potential for addiction, systemic toxicity, and adverse side effects. Einhorn's development of procaine provided a safer and more effective alternative, as it lacked the addictive properties of cocaine and exhibited a lower incidence of side effects. Procaine was initially used in dentistry and minor surgical procedures, quickly becoming a standard anesthetic in clinical practice.

Procaine acts by inhibiting the transmission of nerve impulses in the targeted area, providing localized pain relief. It does this by blocking sodium channels in nerve membranes, preventing the depolarization required for nerve signal propagation. The onset of procaine is relatively quick, with effects typically lasting for about one to two hours, making it suitable for various short-term procedures. Due to its effectiveness and safety profile, procaine became a popular choice among healthcare providers, especially in outpatient settings.

In addition to its use in local anesthesia, procaine has also been utilized in various medical applications. One notable use is in the treatment of chronic pain conditions, where procaine is administered via injection to provide long-lasting pain relief. Its application in this context has gained interest, particularly in alternative medicine and integrative health approaches. Procaine is sometimes used in combination with other therapies to enhance pain management and improve patient outcomes.

Another area of research has explored the potential of procaine in treating conditions such as osteoarthritis and fibromyalgia. Preliminary studies have suggested that procaine may have anti-inflammatory properties, which could contribute to its efficacy in managing pain associated with these conditions. However, further research is needed to establish its effectiveness and safety in these specific applications.

Procaine is also used in the field of aesthetic medicine, particularly in procedures involving dermal fillers and facial rejuvenation. Its local anesthetic properties help minimize discomfort during injection procedures, enhancing patient comfort and satisfaction. The combination of procaine with other injectable agents has become increasingly popular in cosmetic treatments.

Despite its widespread use, procaine is not without limitations. Some individuals may experience allergic reactions or hypersensitivity to procaine, although such occurrences are relatively rare. Additionally, due to its short duration of action, procaine may not be suitable for procedures requiring longer anesthesia. In such cases, healthcare providers may opt for alternative local anesthetics with extended duration.

In summary, procaine is a vital local anesthetic with a significant history of discovery and diverse applications in medicine and dentistry. Its development represented a major advancement in anesthetic practice, providing a safer and more effective alternative to cocaine. Ongoing research continues to explore its potential uses in pain management, aesthetic medicine, and beyond, underscoring its importance in modern clinical practice.

References

1979. Pharmacokinetic Model for Procaine in Humans during and following Intravenous Infusion. Journal of Pharmaceutical Sciences, 68(8).
DOI: 10.1002/jps.2600680826

1979. CYTOTOXIC EFFECTS OF PROCAINE, LIGNOCAINE AND BUPIVACAINE. British Journal of Anaesthesia, 51(4).
DOI: 10.1093/bja/51.4.273

1979. Changes of insulinemia, glycemia and feeding behavior induced by VMH-procainization in the rat. Brain Research, 174(2).
DOI: 10.1016/0006-8993(79)90816-3