Structure
Procaine Chemical Structure – C13H20N2O2
Mode of action
Procaine primarily affects peripheral neurons by blocking sodium inflow through voltage-gated sodium channels in the neuronal cell membrane.
An action potential cannot form when the influx of sodium is inhibited, and signal conduction is so blocked.
Structure-Activity Relationship (SAR) of Procaine
Procaine is a local anesthetic used primarily to reduce the sensation of pain in specific areas of the body.
Its SAR can be summarized as follows:
1. Ester Linkage:
Procaine is an ester-linked local anesthetic, similar to benzocaine.
The ester linkage is crucial for its local anesthetic activity.
It is generally associated with a shorter duration of action and a lower incidence of allergic reactions compared to amide local anesthetics.
2. Aromatic Ring:
The presence of an aromatic ring (benzene) is essential.
This part of the molecule is lipophilic, aiding in its ability to penetrate cell membranes to reach its site of action in nerve cells.
3. Amino Group:
The para-position amino group on the benzene ring is important for anesthetic activity.
This group increases the solubility of the compound in biological fluids.
4. Diethylamino Ethanol Side Chain:
The diethylamino ethanol side chain is crucial for procaine’s activity.
The length and nature of this side chain can significantly affect the drug’s potency and duration of action.
Here is the mind map illustrating the Structure-Activity Relationship (SAR) of Procaine:
Synthesis of Procaine
The synthesis of Procaine typically involves the following key reaction:
Esterification of Para-Aminobenzoic Acid:
C7H7NO2 + C6H14N2O → C13H20N2O2 + H2O
In this reaction, para-aminobenzoic acid (C7H7NO2) is esterified with diethylamino ethanol (C6H14N2O) to form Procaine (C13H20N2O2), along with the production of water (H2O).
This synthesis is a classic example of esterification, a common method in organic chemistry for forming ester compounds.
The reaction typically involves an acid catalyst and must be carried out under controlled conditions to ensure the purity and yield of the procaine.
Uses
Procaine is used for spinal nerve block, peripheral nerve block, and anaesthesia.