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Lidocaine, Xylocaine, Lignocaine, Maricaine, Ligoncaine, Lidocaine Hydrochloride, Lidocaine HCl, 137-58-6, 6108-05-0, 73-78-9

Lidocaine, Xylocaine, Lignocaine, Maricaine, Ligoncaine, Lidocaine Hydrochloride, Lidocaine HCl, 137-58-6, 6108-05-0, 73-78-9

LIDOCAINE

SECTION 1: PRODUCT IDENTITY AND CHEMICAL IDENTIFICATION

Parameter Lidocaine (Base) Lidocaine Hydrochloride
Chemical Name (IUPAC) 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrochloride
Synonyms (Turkish) Lidokain, Lignokain, Ksilokain Lidokain HCl, Lignokain Hidroklorür
Synonyms (English) Lidocaine, Xylocaine, Lignocaine, Maricaine, Ligoncaine Lidocaine Hydrochloride, Xylocaine Hydrochloride
CAS Number 137-58-6 6108-05-0 (dihydrate) / 73-78-9 (anhydrous)
EC Number (EINECS) 205-302-8 205-302-8 (same)
Molecular Formula C₁₄H₂₂N₂O C₁₄H₂₂N₂O · HCl
Molecular Weight 234.34 g/mol 270.80 g/mol
Chemical Class Amide-type local anesthetic Amide-type local anesthetic (hydrochloride salt)
Physical State (20°C) Solid (crystalline powder) Solid (crystalline powder)
Color White to off-white White to off-white
Odor Odorless Odorless
Taste Bitter and numbing Bitter and numbing

SECTION 2: CHEMICAL STRUCTURE

           CH₃
             \
              C
             / \
            /   \
           /     \
    CH₃—C         C—H
        \       /
         \     /
          C—NH—C—CH₂—N(C₂H₅)₂
         /     ‖
        /      O
       /
    CH₃

    Lidocaine (Base)
    2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide
    C₁₄H₂₂N₂O

    HCl salt: Lidocaine Hydrochloride (C₁₄H₂₂N₂O · HCl)

Structure Description:

Parameter Description
Chemical Class Amide-type local anesthetic
Functional Groups Amide (-CO-NH-), tertiary amine (-N(C₂H₅)₂), dimethylphenyl ring
Lipophilic Part 2,6-dimethylphenyl ring (provides anesthetic effect)
Hydrophilic Part Diethylamino group (provides water solubility)
Linkage Amide bond (more stable than ester bond)
SMILES CCN(CC)CC(=O)NC1=C(C)C=CC=C1C
InChI InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
InChI Key HBJZPBCJNUUEHN-UHFFFAOYSA-N
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
Rotatable Bond Count 5
Polar Surface Area (PSA) 32.3 Ų

SECTION 3: PHYSICAL AND CHEMICAL PROPERTIES

Property Lidocaine (Base) Lidocaine Hydrochloride Test Method / Note
Appearance White to off-white crystalline powder White to off-white crystalline powder Visual
Odor Odorless Odorless Olfactometric
Taste Bitter and numbing Bitter and numbing Sensory
Molecular Weight 234.34 g/mol 270.80 g/mol Calculated
Melting Point 66 – 69°C 127 – 129°C DSC / Capillary
Melting Point (Monohydrate) - 77 – 78°C DSC
Boiling Point bp₄ 180-182°C; bp₂ 159-160°C - Vacuum Distillation
Density ~0.9944 g/cm³ (estimated) - Calculated
Refractive Index (nD) ~1.5110 (estimated) - Refractometer
pKa (25°C, H₂O) ~7.88 ~7.88 Potentiometric
Water Solubility Practically insoluble Freely soluble General Method
Ethanol Solubility Soluble (4 mg/mL) Soluble General Method
Ether Solubility Soluble Soluble General Method
Benzene Solubility Soluble Soluble General Method
Chloroform Solubility Soluble Soluble General Method
Oil Solubility Soluble Soluble General Method
pH (0.5% Solution) - 4.0 – 5.5 pH Meter
Vapor Pressure (25°C) 4.28 × 10⁻⁵ mmHg - Calculated
Flash Point >150°C (solid) >150°C (solid) ASTM D93
Stability Stable under normal conditions Stable under normal conditions -
Hygroscopicity Not hygroscopic Slightly hygroscopic -
Log P (Octanol/Water) ~2.44 (lipophilic) - Calculated

SECTION 4: LIDOCAINE BASE vs HYDROCHLORIDE COMPARISON

Property Lidocaine (Base) Lidocaine Hydrochloride
Water Solubility Low (oil-soluble) High (water-soluble)
Main Application Area Oil-based formulations (topical creams, ointments, patches) Aqueous formulations (injectable solutions, eye drops, oral solutions)
Ionization at Physiological pH Mostly non-ionized (higher lipid solubility, faster onset) Ionized (water-soluble, more stable)
Tissue Penetration High (lipophilic) Low (hydrophilic; effective upon injection)
Commercial Forms Topical creams, ointments, patches Injectable ampoules, eye drops, oral gels, dental cartridges
Systemic Absorption Limited in topical application Rapid and complete upon injection

SECTION 5: CHEMICAL PROPERTIES AND REACTIVITY

Parameter Information
Chemical Character Amide-type local anesthetic; weak base (pKa ~7.88)
Stability Stable under normal conditions; amide bond is more resistant to hydrolysis than ester bond
Decomposition Products (Heating) CO, CO₂, NOx, HCl (for salt form)
Incompatible Materials Strong oxidizing agents, strong acids and bases
Hydrolysis Amide bond is more resistant to hydrolysis compared to ester-type anesthetics
Acid-Base Reaction Forms water-soluble salts with acids (lidocaine hydrochloride)
Hazardous Polymerization Does not occur

SECTION 6: LOCAL ANESTHETICS COMPARISON

Property Lidocaine Procaine Bupivacaine Tetracaine Benzocaine
CAS Number 137-58-6 59-46-1 38396-39-3 94-24-6 94-09-7
Class Amide Ester Amide Ester Ester
Onset of Action Rapid (2-5 min) Moderate (5-10 min) Slow (5-10 min) Slow (5-10 min) Slow
Duration Moderate (1-2 h) Short (30-60 min) Long (3-8 h) Long (2-3 h) Short
pKa 7.9 8.9 8.1 8.5 2.5
Maximum Dose 4.5 mg/kg 10 mg/kg 2 mg/kg 1.5 mg/kg Topical
Allergy Risk Very Low Moderate (PABA) Very Low Moderate (PABA) Low
Vasodilation Yes Yes Yes Yes None
Primary Use Infiltration, topical Infiltration, dental Epidural, spinal Spinal, topical Topical

SECTION 7: PHARMACOLOGICAL PROPERTIES AND MECHANISM OF ACTION

Property Description
Mechanism of Action Blocks voltage-gated sodium (Na⁺) channels, inhibiting the generation and conduction of action potentials in nerve cells.
Anesthetic Class Amide-type local anesthetic. Unlike ester-type anesthetics, metabolism occurs in the liver and allergy risk is low.
Onset of Action Rapid (2-5 minutes).
Duration of Action Moderate (1-2 hours); can be extended to 2-4 hours with epinephrine.
Vasodilator Effect Causes local vasodilation; epinephrine is added to slow absorption and prolong duration.
Anti-arrhythmic Effect Class Ib anti-arrhythmic; used in the treatment of ventricular arrhythmias.
Topical Effect Effective on mucosal and skin surfaces; used in spray, gel and cream forms.
Absorption Rapidly absorbed from mucosal surfaces; absorption increases from damaged skin.
Metabolism Hepatic metabolism via CYP3A4 and CYP1A2 enzymes.
Half-Life 1.5 – 2 hours
Elimination Excreted renally via urine (~90% as metabolites)
Protein Binding ~60-70%
Volume of Distribution ~1-2 L/kg

SECTION 8: MAIN APPLICATION AREAS

Application Area Lidocaine (Base) Lidocaine Hydrochloride
Dentistry - Local infiltration anesthesia, nerve block (2%)
Surgery - Minor surgical procedures, epidural anesthesia (1-2%)
Dermatological (Topical) Topical cream, gel, spray (2-5%) -
Ophthalmic - Eye drops (corneal anesthesia) (1-4%)
Cardiology - Ventricular arrhythmia treatment (IV: 1-1.5 mg/kg bolus)
Cosmetic Laser epilation, tattoo removal (2.5-5% cream) Local anesthesia prior to injections
Emergency Medicine - Suturing, catheterization, minor procedures (1-2%)
Topical (Skin) Skin patches, analgesic ointments Oral gels, rinses
Urology - Urethral anesthesia (2% gel)
ENT - Laryngoscopy, bronchoscopy, endoscopy (2-4% spray)

SECTION 9: QUALITY SPECIFICATIONS (PHARMACEUTICAL GRADE - USP/EP)

Parameter Specification (Base) Specification (HCl) Test Method
Appearance White to off-white crystalline powder White to off-white crystalline powder Visual
Odor Odorless Odorless Olfactometric
Assay (on dried basis) 98.0 – 101.0% 98.0 – 101.0% HPLC / Titrimetric
Melting Point 66 – 69°C 127 – 129°C DSC / Capillary
Loss on Drying (105°C, 2 h) ≤0.5% ≤0.5% Gravimetric
pH (0.5% Solution) - 4.0 – 5.5 pH Meter
Chloride (Cl⁻) - 13.7 – 14.5% Argentometric
Sulfated Ash ≤0.1% ≤0.1% Gravimetric
Heavy Metals (as Pb) ≤20 ppm ≤20 ppm ICP-MS / USP <231>
Lead (Pb) ≤3 ppm ≤3 ppm ICP-MS
Arsenic (As) ≤3 ppm ≤3 ppm ICP-MS
Mercury (Hg) ≤1 ppm ≤1 ppm ICP-MS
Cadmium (Cd) ≤1 ppm ≤1 ppm ICP-MS
Related Substances (Single) ≤0.5% ≤0.5% HPLC
Related Substances (Total) ≤1.0% ≤1.0% HPLC
2,6-Dimethylaniline ≤100 ppm ≤100 ppm HPLC
Total Microbial Count ≤100 CFU/g ≤100 CFU/g USP <61>
Yeast and Mold ≤10 CFU/g ≤10 CFU/g USP <61>
E. coli Negative in 1g Negative in 1g USP <62>
Salmonella spp. Negative in 25g Negative in 25g USP <62>
S. aureus Negative in 1g Negative in 1g USP <62>
P. aeruginosa Negative in 1g Negative in 1g USP <62>

SECTION 10: TOXICOLOGICAL PROFILE

Parameter Value
Acute Oral Toxicity (LD50, Rat) ~317 mg/kg
Acute Dermal Toxicity (LD50, Rabbit) >2,000 mg/kg
Acute Inhalation Toxicity Toxic (R23)
Skin Irritation Mild irritant
Eye Irritation Irritant
Inhalation Irritation Inhalation of dust may cause mechanical irritation
Skin Sensitization May cause sensitization (rare)
Carcinogenicity Not classified (IARC, NTP)
Mutagenicity Negative in in vitro tests
Reproductive Toxicity Fetal effects at high doses; use with caution in pregnancy (FDA Category B)
Systemic Toxicity At high doses: dizziness, tinnitus, convulsions, cardiac depression
Maximum Safe Dose (Adult) 4.5 mg/kg (without epinephrine); 7 mg/kg (with epinephrine)
NOAEL (Rat, 90 days) ~50 mg/kg/day
Target Organs Nervous system, heart, liver

SECTION 11: GHS CLASSIFICATION AND LABELING

GHS Classification (in accordance with 1272/2008/EC):

Hazard Class Category H-Statement
Acute Toxicity (Oral) Category 3 H301
Acute Toxicity (Dermal) Category 3 H311
Acute Toxicity (Inhalation) Category 3 H331
Skin Irritation Category 2 H315
Eye Irritation Category 2 H319
STOT - SE Category 3 H335

Signal Word: DANGER

Hazard Pictograms: GHS06 (Skull and Crossbones)

Hazard Statements (H-Codes):

Code Statement
H301 Toxic if swallowed
H311 Toxic in contact with skin
H315 Causes skin irritation
H319 Causes serious eye irritation
H331 Toxic if inhaled
H335 May cause respiratory irritation

NFPA 704 Hazard Classification:

Health Flammability Reactivity Special
2 0 0 -
(Moderate health hazard) (Non-combustible) (Stable) (None)

SECTION 12: PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P261 Avoid breathing dust/fume/gas
P264 Wash hands thoroughly after handling
P270 Do not eat, drink or smoke when using this product
P271 Use only outdoors or in a well-ventilated area
P280 Wear protective gloves/protective clothing/eye protection/face protection
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor
P302+P352 IF ON SKIN: Wash with plenty of soap and water
P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and continue rinsing
P311 Call a POISON CENTER/doctor
P321 Specific treatment (see label instructions)
P330 Rinse mouth
P332+P313 If skin irritation occurs: Get medical advice/attention
P337+P313 If eye irritation persists: Get medical advice/attention
P362+P364 Take off contaminated clothing and wash it before reuse
P403+P233 Store in a well-ventilated place. Keep container tightly closed
P405 Store locked up
P501 Dispose of contents/container in accordance with local/regional/national/international regulations

SECTION 13: FIRST AID MEASURES

Route of Exposure Action
Inhalation Remove to fresh air immediately. Get medical attention if respiratory difficulty persists. If breathing has stopped, perform artificial respiration.
Skin Contact Remove contaminated clothing immediately. Wash with plenty of soap and water for at least 15 minutes. Get medical attention.
Eye Contact Rinse immediately with plenty of water for at least 15 minutes. Keep eyelids open. Remove contact lenses if present. Get immediate medical attention.
Ingestion Rinse mouth with water. Do NOT induce vomiting. Get immediate medical attention and show the container or label.
Systemic Toxicity Symptoms Dizziness, tinnitus, numbness around the mouth, confusion, muscle twitching, convulsions, loss of consciousness, respiratory depression, cardiac arrhythmia. If these symptoms occur, seek immediate medical attention.
Note to Physician Toxicity management: Benzodiazepines (diazepam) for convulsions; atropine and epinephrine for cardiac depression. No specific antidote.

SECTION 14: FIREFIGHTING MEASURES

Parameter Information
Fire Hazard Combustible (solution forms are highly flammable)
Flash Point 9°C (in solution form)
Fire-Related Hazards CO, CO₂, NOx, HCl (for salt form)
Suitable Extinguishing Media Water mist, CO₂, dry chemical powder, alcohol-resistant foam
Unsuitable Extinguishing Media Water jet (may spread burning material)
Special Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing
Special Precautions Prevent firefighting water from entering water bodies. Avoid dust cloud formation.

SECTION 15: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Room temperature (15-25°C), dry, well-ventilated area, light-protected containers.
Temperature Limits 15-25°C (ideal); do not exceed 30°C
Humidity Low humidity environment (especially for HCl salt)
Light Light-proof containers (amber glass, HDPE, aluminum)
Container Requirements Tightly closed, light-proof, moisture-resistant containers
Incompatible Materials Strong oxidizing agents, ignition sources, moisture (for HCl salt)
Shelf Life 36-60 months (unopened original packaging, under proper storage conditions)
Signs of Degradation Color change (yellowing), caking, odor change, HPLC impurity increase
Stability Note Stable under normal conditions; amide bond is more stable than ester anesthetics

SECTION 16: PACKAGING OPTIONS

Packaging Type Quantity Material Application Area
Aluminum Foil Bag 1 kg, 5 kg Laminated aluminum / PE (light and moisture proof) High purity, pharmaceutical
Fiber Drum (PE Lined) 25 kg Cardboard + PE liner Industrial supply
HDPE Drum 25 kg, 50 kg HDPE (opaque, moisture barrier) Pharmaceutical manufacturing
Amber Glass Bottle 100 g, 500 g, 1 kg Amber glass (UV protected) Laboratory, analytical standards
Kraft Bag (PE Lined) 10 kg, 25 kg Kraft paper / PE liner Economical packaging
IBC Container 500 kg, 1000 kg UV-protected HDPE Large-scale industrial supply

SECTION 17: TRANSPORTATION INFORMATION

Parameter Information
UN Number UN 3249 (Toxic Solid, Organic, N.O.S.)
Hazard Class 6.1(b) (Toxic Substances)
Packing Group III
ADR/RID UN 3249, Toxic Solid, 6.1, PG III
IMDG Code UN 3249, Toxic Solid, 6.1, PG III
IATA (Air) UN 3249, Toxic Solid, 6.1, PG III
Marine Pollutant No
Transport Temperature Ambient temperature
Transport Precautions Keep away from heat sources, ignition sources and oxidizing agents. Light-proof packaging.
Spill Cleanup Avoid dust generation. Collect mechanically. Clean with absorbent material. Do not allow to enter sewers or water bodies.

SECTION 18: REGULATORY STATUS

Region / Authority Status
USA (USP-NF) Official monograph (USP Lidocaine; Lidocaine Hydrochloride)
European Pharmacopoeia Official monograph (Ph. Eur. Lidocaine; Lidocaine Hydrochloride)
USA (FDA) Prescription drug; OTC topical forms approved
WHO Essential Medicines List Essential medicine (local anesthetic and anti-arrhythmic)
Turkey Licensed pharmaceutical active ingredient; prescription drug; KKDIK registered
REACH (EU) Registered substance
TSCA (USA) Listed
DEA / Controlled Substance Not a controlled substance
IARC Not classified (not carcinogenic)
NTP Not listed
OSHA Regulated as hazardous substance
California (Prop 65) Not listed

SECTION 19: OTHER NAMES AND SYNONYMS

Type Name
Chemical Names 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide; 2-(Diethylamino)-2',6'-acetoxylidide
Common Names (Turkish) Lidokain, Lignokain, Ksilokain
Common Names (English) Lidocaine, Xylocaine, Lignocaine, Maricaine, Ligoncaine
Salt Form Lidocaine Hydrochloride (CAS 73-78-9 / 6108-05-0)
CAS Number (Base) 137-58-6
CAS Number (HCl) 6108-05-0 (dihydrate) / 73-78-9 (anhydrous)
EC Number 205-302-8
HS Code 2924.29

SECTION 20: SUMMARY TABLE

Parameter Lidocaine (Base) Lidocaine Hydrochloride
CAS Number 137-58-6 6108-05-0 / 73-78-9
Molecular Formula C₁₄H₂₂N₂O C₁₄H₂₂N₂O · HCl
Molecular Weight 234.34 g/mol 270.80 g/mol
Appearance White to off-white crystalline powder White to off-white crystalline powder
Melting Point 66 – 69°C 127 – 129°C
Water Solubility Practically insoluble Freely soluble
pKa ~7.88 ~7.88
Primary Function Amide-type local anesthetic; Class Ib anti-arrhythmic Amide-type local anesthetic; Class Ib anti-arrhythmic
Main Application Oil-based topical formulations Aqueous formulations (injection, eye drops)
Shelf Life 36-60 months 36-60 months
GHS Signal Word DANGER DANGER
UN Number UN 3249 UN 3249
Hazard Class 6.1(b) 6.1(b)

SECTION 21: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

  1. Systemic Toxicity: High doses or intravascular injection can cause serious cardiac and neurological toxicity. Maximum dose must not be exceeded.

  2. Dose Calculation: Maximum adult dose is 4.5 mg/kg (without epinephrine) and 7 mg/kg (with epinephrine). Pediatric doses should be adjusted.

  3. Allergy: As an amide-type anesthetic, there is no cross-allergy risk with ester-type anesthetics (procaine, benzocaine). However, caution should be exercised if there is any history of allergy.

  4. Aspiration: Always aspirate before injection; avoid intravascular injection.

  5. Flammable Solution: Solution forms are highly flammable; keep away from ignition sources.

  6. Pregnancy: FDA Category B; use during pregnancy only if clearly necessary.

  7. Topical Use: Rapidly absorbed from mucous membranes and damaged skin; calculate total dose when applying to large surfaces.

BEST PRACTICE RECOMMENDATIONS:

  1. Correct Form Selection: Choose the correct form based on the application. Use Lidocaine Hydrochloride for aqueous solutions and Lidocaine Base for oil-based topical formulations.

  2. Epinephrine Use: Adding a vasoconstrictor (epinephrine) slows absorption, prolongs duration, and reduces systemic toxicity risk.

  3. Aspiration: Always aspirate before injection; avoid intravascular injection.

  4. Topical Use: Rapidly absorbed from mucous membranes and damaged skin; calculate total dose when applying to large surfaces.

  5. Stability: Amide bond is more stable than ester bond; provides long shelf life.

  6. Storage: Store at room temperature in light-protected containers; keep away from strong oxidizing agents.

  7. Personal Protective Equipment: Chemical-resistant gloves, safety goggles or face shield, protective clothing (lab coat), dust mask (N95/FFP2).

  8. Hygiene: Wash hands thoroughly after handling; Do not eat, drink or smoke when using this product.

LEGAL DISCLAIMER:

The information provided in this document is based on our current knowledge and experience and is presented in good faith. However, as all conditions of use are beyond our control, it does not constitute a binding specification or guarantee. This Technical Data Sheet is for informational purposes only and does not constitute medical advice. Users are responsible for testing suitability for their own applications and for complying with all local, regional, and national regulations. For complete safety, storage, use, handling, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Lidocaine is a pharmaceutical active ingredient; its use must be under the supervision of a healthcare professional.

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