CLASSIFICATION OF LOCAL

ANESTHETICS

By

Helen R. Hallare, DDM

 Chemical Groups of LOCAL
ANESTHETICS commonly used in
dentistry:

I. Ester group
A. Benzoic acid esters
1. Cocaine (topical only) naturally
occurring
2. Benzocaine (topical only)
Chemical Groups of LOCAL ANESTHETICS
commonly used in dentistry:

B. Para-aminobenzoic acid esters

1. Procaine (Novocaine)
2. Tetracaine (Pontocaine) extremely
strong local anesthetic for surface
anesthesia; no real injection use
3. Propoxycaine (Ravocaine)
4. 2-Chloroprocaine (Nesacaine) (not
marketed in an dental cartridge)
Chemical Groups of LOCAL ANESTHETICS
commonly used in dentistry:

II. Nonester group

A. Anilide (Nonester type)
1. Bupivacaine (Marcaine,
Sensorcaine)
2. Etidocaine (Duranest)
3. Lidocaine (Xylocaine)
4. Mepivacaine (Carbocaine)
5. Prilocaine (Citanest)
 Excretion and Absorption of Local
Anesthetics
1. Esters: Hydrolyzed by plasma
esterase and by products
excreted in urine. Note that one
by product is PABA (para-amino
benzoic acid)
2. Amides: Metabolized in liver by
microsomal enzymes and only 10—
20% is excreted unchanged
 Cocaine
From the leaves of a plant called
Erthroxylon coca; 1855 French chemist
F. Gaedcke
Albert Niemann isolated the alkaloid in
its pure form—named it ‘cocaine’
1884, Carl Koller, encouraged by
Sigmund Freud, discovered that it is
effective surface anesthesia of the
cornea
 Cocaine
William Steward Halsted in America
used the solution to produce anesthesia
in the inferior dental nerve; victim of
the drug’s addictive properties
First record of use in Britain, JADA
1886, William Alfred Hunt described
use in infiltration
1901, E. Mayer suggested addition of
adrenaline—promote vasoconstriction,
prolong duration, and intensify depth of
anesthesia
 Cocaine
Rarely used these days due to problems
of misuse
Methyl 3β-hydroxy-1αH-tropan-2β-
carboxylate ester benzoate (chemical
name)
Unique among local anesthetic agents in
that it produces vasoconstriction
 Cocaine
Preparation:
Topical preparation as a 4 - 10% solution
Recommended uses in Dentistry:
Should not be considered as a normal part
of dental local anesthetic armamentarium
due to its obvious disadvantage—potential
for abuse
Occasionally used topically intranasally
during apical surgery on maxillary incisor
teeth when the nasal floor is in close
proximity
 Benzocaine
Most commonly used ester local
anesthetic
Ethyl-p-aminobenzoate (chemical name)

Dosage
Due to its extremely poor solubility in
water and poor absorption, toxic
reactions to benzocaine are almost
unknown
 Benzocaine
Preparation:
 Extremely poor water solubility – not
suitable for injection; available only in
topical preparations
 Available in number of concentrations
up to 20% and in combination with other
agents
 Different flavors have been added to
benzocaine gel to make them
particularly popular with children
 Benzocaine
Recommended uses in Dentistry:
Topical application prior to an
infiltration – means of reducing pain
Incorporated into proprietary
medications for application to painful
intraoral lesions – ulcers
Sole source of anesthesia for
superficial soft tissue manipulation
 Procaine
Produced synthetically procaine
hydrochloride by two Swedish chemists,
Alfred Einhorn & E. Uhlfelder
Tested clinically by Henrich Braun and
marketed as Novocaine (proprietary
name)
Archetypal dental local anesthetic prior
to the introduction of lignocaine
 Procaine

Use has declined for a number of

reasons: susceptible persons may
become sensitized to this substance;
can cause dermatitis, urticaria and even
eodema of the glottis
Not as potent as cocaine, but it is very
much less toxic
 Procaine
Preparation:
Rarely used as sole anesthetic in
Dentistry today
No longer available in cartridges in some
parts of the world and must be drawn up
in ampule
Normal presentation is 2% solution,
however 1:80,000 adrenaline may be
added
Not available as a topical agent
 Procaine
Recommended uses in Dentistry
Only indication for use as a local
anesthetic is in patients with proven
allergy to the amide group
Useful in intravenous sedation relevant
to dental practice
Recognized regimen to treat
arteriospasm when it is administered
intra-arterially – excellent vasodilatory
properties
 Procaine
Onset and duration of action
Onset of action: 10 minutes (pulpal)
Duration of action: plain solution,
extremely short-lived pulpal anesthesia
of approximately 5 minutes
solution with adrenaline, pulpal
anesthesia of 30 minutes
Dosage
Maximum dose is 6 mg/kg with ceiling of
400 mg
 Tetracaine
Para-butylaminobenzoyl-2-
dimethylaminoethanol hydrochloride
(chemical name)
Proprietary name: Pontocaine
10x as potent and 10x as toxic as
procaine
Chemically it is closely related to
procaine but pharmacologically it is
closer to cocaine
Potent topical agent, does not possess
vasoconstricting properties
 Tetracaine

Popular for the production of spinal

anesthesia
No longer available in cartridges for use
in dentistry
Limited almost exclusively to topical
application
Rapidly absorbed into systemic
circulation—toxic effects, not sprayed
on mucous membrane
 Tetracaine
Preparation
 0.15%, 1% and 2% topical solutions

 Plain tetracaine hydrochloride

 Tetracaine hydrochloride with

1:100,000 vasodilator
Dosage
 Maximum of 20 mg (1 ml of 2% solution)
be applied at one time
 Tetracaine

Duration of action
When injected, plain 0.15% solution will
produce 30 – 45 minutes of analgesia
Same concentration with 1:100,000
epinephrine will produce 75 – 120
minutes of analgesia
 Tetracaine
Recommended use in Dentistry
 Although efective when given by
injection, it is not used in this manner
due to its toxicity.
 It is available in topical preparations
both on its own and in combination with
other anesthetic agents such as
lignocaine
 Propoxycaine (Ravocaine)
2-diethylaminoethyl 4-amino-2-
propoxybenzoate is its chemical name
Equal in potency and toxicity to
tetracaine
Preparation
Not used alone in dentistry, combined
with procaine, in a procaine 2%,
propoxycaine 0.4% solution with either
1:20,000 levondefrin or 1: 30,000
levarterenol as vasoconstrictor
 Propoxycaine
Duration of action
 Combination of procaine and propoxycaine
gives rapid and profound anesthesia with
a pulpal analgesia of about 1 – 1.5 hours
and soft tissue duration of 2 – 3 hours
Dosage
 Suggested maximum dose is 6.6 mg’kg (3
mg/lb)
 Maximum total anesthetic (procaine plus
propoxycaine) dosage should not exceed
400 mg
 2-Chloroprocaine
Proprietary name: Nesacaine
Beta-diethylaminoethyl-2-chloro-4-
aminobenzoate (chemical name)
Differs from other local anesthetic of
the ester group in having a chloride
atom substituted in the benzene ring
2x as potent but less toxic than
procaine – hydrolyzed 4x-5x faster than
procaine
 2-Chloroprocaine
Preparation
 Not available in dental cartridge,
multiple dose vial via disposable 3 to 5
cc syringe with a 25-gauge Leur-Lok
needle
 Available in 1.2% or 3% concentrations,
must be used with a vasoconstrictor due
to its shortness of duration
 2-Chloroprocaine

Onset and duration of action

 Extremely rapid onset with a
satisfactory short-acting anesthetic
(low toxicity) thus advantageous in use
for children who may inadvertently
traumatize the lip, tongue or cheek with
longer-acting agents
 Lignocaine
Most commonly used dental anesthetic
Synthetized in 1943, has been in clinical
use since 1948
Proprietary names: Xylocaine, Lignospan,
Lignostab, & Lidocaine (North America)
Chemical name: 2-diethylamino-2,6-
acetoxylidide.
2x potency than procaine
More profound anesthesia and long
duration (spreads more widely through
tissues)
 Lignocaine
Preparations:
Dental cartridges – plain 2%
solution and a 2% solution with
1:80,000 or 1:100,000 adrenaline
Topical – 4% and 10% spray, 2%
gels, and 5% ointment
 Lignocaine

Recommended uses in Dentistry:

2% with 1:80,000 adrenaline--ideal for
infiltration, intraosseous,
intraligamentary, and regional block
anesthesia for majority of patients
Contraindicated in those allergic to
amides and in individuals where
increased adrenaline levels may be
hazardous
 Lignocaine

Recommended uses in Dentistry:

Plain solution is not very effective in
obtaining pulpal anesthesia
Use for soft tissue procedures is very
limited—poor hemorrhage control
Nevertheless, effective topical
anesthetic for non-keratinized tissue:
reflected mucosa & as a symptomatic
treatment for painful mucosal lesions
such as ulcers
 Lignocaine
Onset and duration of action
Short onset of action, pulpal anesthesia
obtained in 2-3 minutes ff. infiltration
Plain solution is classified as short-acting
agent, will provide pulpal anesthesia for 10
minutes; 1-1 ½ hours soft tissue anesthesia
Adrenaline containing solution is
intermediate in duration providing 45-60
minutes (1-1 ½ hours) of pulpal anesthesia;
3-4 hours soft tissues anesthesia
 Prilocaine
Toluidine derivative; related both
chemically and pharmacologically to both
lignocaine and mepivacaine
Proprietary name: Citanest
2-propylamino-o-propionotoluidine
(chemical name)
As potent as lignocaine but is less toxic
Metabolized more rapidly than
lignocaine
Does not produce topical anesthesia
 Prilocaine
Preparations
Plain solution is 4%
Vasoconstrictor-containing version is
3% with 0.03 IU/ml felypressin (UK)
In other parts of the world prilocaine is
available with adrenaline
Topical anesthetic agent available –
combination prilocaine & lignocaine
EMLA (Eutectic Mixture of Local
Anesthetics)
 Prilocaine
Recommended use in Dentistry
3% with 0.03 IU felypressin is the alternative to
lignocaine with adrenaline when a vasoconstrictor-
containing solution is required
Effective when administered as an infiltration or
regional block anesthetic
Not as effective as lignocaine during
intraligamentary techniques
4% plain prilocaine more effective than 2%
lignocaine when a vasoconstrictor-free solution
must be employed
EMLA useful prior to venepuncture in children
and during dental sedation; oral application not
recommended by manufacturers
 Prilocaine
Contraindications
Should not be administered to infants,
patients with methaemoglobineamia, kidney
disease, hypoxia, anemia, liver disease or
heart failure, or any other condition in which
problems with oxygenation could be critical,
such as pregnancy
Should not be used in patients who have a
history of either sensitivity to an amide-type
local anesthetic agent or paraben allergy
 Prilocaine
Onset and duration of action
Slower onset of action than lignocaine:
pulpal anesthesia 4 minutes
4% prilocaine short-acting agent with
pulpal anesthesia lasting around 10
minutes
3% with 0.03 IU felypressin provides
duration of anesthesia similar to that
afforded by lignocaine
 Mepivacaine
The least vasodilatory of the amide
local anesthetic
Proprietary name: Scandonest (UK),
Carbocaine Pharmaceutical
Manufacturing Co.
1-methyl-2,6-pipecoloxylidide (chemical
name)
Mepivacaine without adrenaline has a 5-
year shelf-life, irrespective of the
conditions of storage
 Mepivacaine

Preparations
3% plain solution
2% solution with 1:80,000
adrenaline
Not available in a topical
preparation
 Mepivacaine
Recommended use in Dentistry:
Prime indication is for the use is when
vasoconstrictor-free solution must be
employed as 3% mepivacaine is more
effective than plain lignocaine or
prilocaine solutions
Solution with adrenaline has identical
indications for use as lignocaine with
adrenaline although it has a shorter
duration of action
 Mepivacaine

Onset and duration of action

Rapid onset of action: (pulpal) 2 minutes
Duration of action:
(pulpal) plain solution—30 minutes
with adrenaline provides anesthesia
of similar depth as lignocaine but of
slightly shorter duration
 Dosages

Anesthetic Max. Max. dose Max. dose Max. dose Max. dose
solution dose of 1.8 ml of 1.8 ml of 2.2 ml of 2.2 ml
(mg/kg) cartridges cartridges in cartridges cartridges in
[absolute in an adult a 5-year-old in an adult a 5-year-old
ceiling of 70 kg child of 20kg of 70 kg child of 20kg
(mg)]
2% lignocaine 4.4 [300] 8.3 2.4 6.8 2

2% mepivacaine 4.4 [300] 8.3 2.4 6.8 2

3% mepivacaine 4.4 [300] 5.6 1.6 4.5 1.3

3% prilocaine 6.0 [400] 7.4 2.2 6 1.8

4% prilocaine 6.0 [600] 5.5 1.7 4.5 1.4

 Bupivacaine
Developed from mepivacaine and is thus
chemically related to lignocaine
Differs from mepivacaine in that a
methyl group in the piperidine ring has
been replaced by a butyl group
Proprietary name: Marcaine,
Sensorcaine
1-butyl-2,6-pipecoloxylidide (chemical
name)
4x as potent as lignocaine
 Bupivacaine
Preparations:
Has recently been available to the
dental profession in conventional 1.8 ml
cartridges
Supplied in 10,30, & 50 ml vials
containing 0.25%, 0.375%, 0.5%, 0.75%
solutions available with or without
1:200,000 adrenaline
 Bupivacaine
Recommended uses in Dentistry
Few indications in routine restorative
dentistry
Main uses are in oral surgery—regional
block, long lasting anesthesia
Useful for post-operative pain control
following procedures such as the
surgical removal of impacted third
molars
Short-term temporary relief of acutely
painful conditions—trigeminal neuralgia
 Bupivacaine
Onset and duration of action:
Onset of action: longer than lignocaine,
may take more than 5 minutes pulpal
anesthesia
Duration of action: longer 1.5 – 2 hours
pulpal anesthesia
When used as a regional block, soft
tissue anesthesia of 6 – 8 hours is
possible
 Bupivacaine
Dosage
 Total doses in the healthy adult should
not exceed 2.0 mg/kg (0.9 mg/lb), not
to exceed 225 mg with epinephrine
1:200,000 and 175 mg without
vasoconstrictor.
 These total doses may be repeated up
to once every 3 hours not to exceed
400 mg in 24 hours
 Etidocaine

Amide derivative that is structurally

similar to lidocaine
4x as potent as lidocaine, with a twofold
increase in the duration of action, twice
as toxic
Proprietary name: Duranest
2-ethylpropylethylbutyroxylidide
(chemical name)
 Etidocaine

Preparations:
Dental local anesthetic cartridges as
1.5% solution with 1:200,000 adrenaline

Onset and duration of action

Onset of action: 2 – 3 minutes pulpal
Duration of action: long-acting
anesthetic similar to bupivacaine
 Etidocaine

Recommended use in Dentistry:

Main indications for use are similar to
those mentioned for bupivacaine as a
regional block anesthetic
When used in infiltration techniques for
surgical procedures 1.5% etidocaine
with 1:200,000 adrenaline is not as
effective as 2% lignocaine with 1:80,000
adrenaline