Is Lignocaine an Amide or Ester?

Lignocaine, also known as lidocaine, is one of the most widely used local anesthetics in medicine. But there is often confusion around whether lignocaine is classified as an amide or ester. This comprehensive guide will provide a definitive answer on the chemical classification of lignocaine.

What is Lignocaine?

Lignocaine, or lidocaine, is a common local anesthetic and antiarrhythmic drug. It is used for numbing tissue during medical procedures, such as dental work, minor surgery, endoscopies, and biopsies.

Lignocaine works by blocking sodium channels and inhibiting the conduction of nerve impulses, which produces temporary numbness and pain relief. The effects of lignocaine typically occur within minutes of administration and last for 30 to 120 minutes.

Lignocaine was first synthesized in 1943 by Swedish chemist Nils Löfgren and is on the World Health Organization’s List of Essential Medicines. It is available in various formulations, including solutions for injection, gels, sprays, creams, ointments, and patches.

Mode of Administration

Lignocaine can be administered via:

• Injection – Given subcutaneously for minor procedures or nerve blocks. Also used intravenously for arrhythmia treatment.
• Topical application – Gels, creams and patches applied directly to the skin or mucous membranes. Used for minor wounds, hemorrhoids, teething, and more.
• Inhaled – Solutions inhaled via nebulizer for bronchoscopies or intubation.
• Intravenous regional anesthesia – Extremities are exsanguinated then IV lignocaine is given to anesthetize the blocked arm or leg.

Uses of Lignocaine

Some common uses of lignocaine include:

• Local anesthesia for minor surgery and dental work
• Biopsies, lumbar punctures, bone marrow aspiration
• Catheter insertion
• Endoscopies like colonoscopies, cystoscopies, bronchoscopies
• Antiarrhythmic for ventricular tachycardia or fibrillation
• Topical anesthetic for hemorrhoids, wounds, teething babies
• Nerve blocks for hand, arm, leg or foot surgery

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Chemical Classification of Lignocaine

With the background on what lignocaine is, we can now definitively answer whether it is an amide or ester type of local anesthetic.

Lignocaine is an Amide-Type Local Anesthetic

Lignocaine, or lidocaine, belongs to the amide class of local anesthetics.

Specifically, it contains an amide linkage between the aromatic portion and intermediate chain. The amide linkage is what classifies lignocaine and related anesthetics as amides.

Other examples of amide local anesthetics include:

• Mepivacaine
• Prilocaine
• Ropivacaine
• Bupivacaine
• Etidocaine

Chemistry Behind Amide Local Anesthetics

To fully understand why lignocaine is classed as an amide, we need to explore the chemical structure and bonding that defines this group.

The Amide Bond

Amide local anesthetics contain a characteristic amide bond – hence their name.

The amide bond is formed between an amine group (-NH2) and a carboxyl group (-COOH). This creates a new amide functional group (-CONH2).

For lignocaine specifically, the amide bond forms between the aromatic diethylamino end and the intermediate chain diethylamide end.

Aromatic Portion

The aromatic portion is a benzene ring with various attached functional groups.

For lignocaine, there are two ethyl groups attached to an amine nitrogen atom. This gives the local anesthetic its “caine” suffix.

Intermediate Chain

The intermediate chain links the aromatic end and amine end.

In lignocaine, it consists of a 2-6 carbon diethylamide chain. Varying the chain length alters the anesthetic potency and duration.

Amine End

The amine group (-NH2) forms one half of the amide bond with the carboxyl group.

Structural variations here allow differentiation between the many amide anesthetics. Lignocaine specifically contains a tertiary amine group.

Complete Structure

Putting it all together, the complete chemical structure of lignocaine is:

2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

The aromatic benzene ring, intermediate diethylamide chain, and tertiary amine group classify lignocaine as an amide local anesthetic both functionally and structurally.

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Key Properties of Lignocaine

Understanding the unique properties of lignocaine provides further insight into its classification and clinical applications.

Onset and Duration

Lignocaine has a fast onset of action, typically within 1-5 minutes of administration. However, it has an intermediate duration of action, lasting approximately 1-2 hours.

This compares to the ultra-short action of esters like procaine, versus the prolonged effects of amides like bupivacaine.

Potency

Lignocaine has an intermediate potency compared to other local anesthetics. It is approximately half as potent as bupivacaine for example.

However, lignocaine has a high therapeutic index meaning the dose can be increased substantially before toxicity occurs. This makes it very versatile for different analgesic needs.

Vasodilation

Unlike many other local anesthetics, lignocaine causes vasodilation (dilation of blood vessels). This increases localized blood flow to the administration site.

Vasodilation enhances absorption into nerve tissues while also speeding the metabolism and elimination from the body.

Metabolism

Lignocaine undergoes hepatic metabolism in the liver. It is broken down into inactive metabolites which are then excreted renally.

Metabolism by plasma esterases is minimal, again highlighting it is an amide rather than ester compound.

Allergenicity

Lignocaine rarely causes allergic reactions, even after repeated exposures. This contrasts with the ester procaine which commonly provokes sensitization.

The low allergenicity makes lignocaine a go-to choice when patients have amide versus ester allergies.

Clinical Uses of Lignocaine

Given its unique properties, lignocaine has been a workhorse local anesthetic for over half a century. Some prime examples of its clinical utility include:

Local Anesthesia

Lignocaine provides safe, effective, and reversible numbness for minor dermatological procedures like:

• Laceration repair
• Biopsies
• Dilatation and curettage
• Wound debridement
• Drainage of abscesses
• Suturing

It can be injected subcutaneously or applied topically depending on need. The fast onset resolves pain quickly during treatment.

Dentistry

Dentists widely use lignocaine as a local anesthetic for procedures like:

• Cavity fillings
• Tooth extractions
• Root canals
• Gum surgeries
• Orthodontic repairs

It is often combined with other agents like epinephrine to provide deeper diffusion and plexus anesthesia.

Labor and Delivery

For women in labor, lignocaine helps provide:

• Perineal anesthesia during the second stage
• Paracervical blocks for short procedures
• Post-delivery repair of lacerations and episiotomies

It provides rapid pain control while enabling women to remain awake and active during birth.

Cardiac Arrhythmias

Intravenous lignocaine can be used to treat certain types of arrhythmias, especially ventricular tachycardia and fibrillation.

Its fast onset and short duration allows titratable control of heart rhythm disorders.

Endoscopies

Applied topically or inhaled, lignocaine suppresses the gag reflex and anesthetizes mucosal tissues during:

• Bronchoscopies
• Laryngoscopies
• Endoscopic retrograde cholangiopancreatography (ERCP)
• Transesophageal echocardiograms (TEE)

This provides procedural tolerance and patient comfort.

Regional Anesthesia

Lignocaine is a foundational agent for regional nerve blocks including:

• Brachial plexus blocks
• Ankle blocks
• Digital blocks
• Field blocks

It produces targeted anesthesia to numb specific limbs or digits during surgery while allowing patients to remain conscious.

This list highlights the broad utility and value of lignocaine across medical specialties thanks to its distinct pharmacologic properties.

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Safety Profile of Lignocaine

When used appropriately, lignocaine has an impressive safety profile and is considered very low risk. However, some side effects are possible.

Common Side Effects

Mild side effects occur occasionally after administration, including:

• Pain or burning at injection site
• Unpleasant taste
• Numbness of the tongue
• Dizziness
• Ringing in the ears
• Nausea
• Blurred vision

These adverse effects are generally transient and resolve without issue once the lignocaine wears off.

Allergic Reactions

Allergic reactions to lignocaine are rare but can potentially occur. Symptoms may include:

• Rash
• Hives
• Itching
• Swelling
• Anaphylaxis in severe cases

Those with hypersensitivities, asthma, or prior reactions to amide anesthetics are at highest risk.

Systemic Toxicity

If excessive doses are given intravenously, lignocaine can cause neurological and cardiac toxicity. Symptoms may include:

• Muscle twitching
• Seizures
• Abnormal heart rhythms
• Hypotension
• Respiratory depression

However, toxicity generally only occurs with high IV doses or when elimination is impaired.

With proper dosing and monitoring as per protocols, lignocaine administration is very safe. The benefits far exceed the minimal risks for most patients.

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Future Outlook for Lignocaine Use

Lignocaine has a proven track record of safety and efficacy over many decades. It continues to be one of the most widely used local anesthetic agents across medical fields.

With its versatility, potency, and low allergenicity, lignocaine is likely to remain a staple anesthetic for the foreseeable future. However, there are some evolving trends that may impact its use:

• Newer amide agents like ropivacaine gaining popularity for certain applications, like labor epidurals
• Topical anesthetic gels replacing injections for some minor dermatology and dental procedures
• Liposomal formulations providing slower release and prolonged anesthesia
• Combination agents with steroids, NSAIDs, and other drugs under development
• Resistant arrhythmias prompting higher doses or exploration of other antiarrhythmics

While these developments may shift preferences in some situations, lignocaine’s unique mix of speed, flexibility and proven reputation ensures it will continue to play a leading role.

Ongoing research also aims to further refine the safety profile and add new delivery methods to improve patient outcomes. After 80 years of lignocaine dominance, its future certainly seems secure as a top amide anesthetic.

Conclusion

In conclusion, lignocaine is definitively classified as an amide-type local anesthetic.

This is evidenced by its distinct amide chemical linkage between an aromatic end and intermediate chain. Lignocaine’s properties such as metabolism, allergenicity, and duration of action are characteristic of the amide class.

Structurally and functionally, lignocaine differs significantly from ester anesthetics like procaine or benzocaine. It will reliably exhibit amide-like clinical effects.

With its versatile pharmacology and extensively documented efficacy, lignocaine has cemented its status as the gold standard amide anesthetic over several decades of use. It provides an optimal balance of rapid onset, flexible potency, and intermediate duration of action.

For the foreseeable future, lignocaine is poised to maintain its place as a core anesthetic agent across medical fields ranging from dentistry to cardiac electrophysiology. Its classification as an outstanding amide anesthetic will continue enabling safe, effective, localized pain control.