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Benzocaine, Ethyl 4-Aminobenzoate, 94-09-7

Benzocaine, Ethyl 4-Aminobenzoate, 94-09-7

BENZOCAINE

PRODUCT IDENTIFIER INFORMATION

Parameter Information
Product Name Benzocaine
Chemical Name (IUPAC) Ethyl 4-aminobenzoate
CAS Number 94-09-7
EC Number (EINECS) 202-303-5
Molecular Formula C9H11NO2
Molecular Weight 165.19 g/mol

SECTION 1: CHEMICAL IDENTITY AND DESCRIPTION

Parameter Information
Chemical Name (IUPAC) Ethyl 4-aminobenzoate
Systematic Name 4-Aminobenzoic Acid Ethyl Ester
Synonyms Benzocaine, Ethyl 4-Aminobenzoate, p-Aminobenzoic Acid Ethyl Ester, Anaesthesin, Anesthone
Trade Names Anbesol, Orajel, Lanacane, Solarcaine, Dermoplast
CAS Number 94-09-7
EC Number (EINECS) 202-303-5
Molecular Formula C9H11NO2
Molecular Weight 165.19 g/mol
Chemical Class Ester-type local anesthetic (para-aminobenzoic acid ester)
Physical State (20°C) Solid (white crystalline powder)
Odor Odorless
Taste Slightly bitter; temporary numbness on tongue

SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES

Property Value Test Method
Appearance White crystalline powder Visual
Odor Odorless Olfactometric
Taste Slightly bitter; temporary numbness Sensory
Molecular Weight 165.19 g/mol Calculated
Melting Point 88 – 90°C DSC / Capillary Tube
Boiling Point 172°C (decomposes) TGA
Density ~1.17 g/cm3 ASTM D4052
pKa (25°C) ~2.5 (aromatic amine) Potentiometric
Solubility in Water (25°C) Slightly soluble (~1.3 g/L) Gravimetric
Solubility in Ethanol Soluble General Method
Solubility in Ether Soluble General Method
Solubility in Chloroform Soluble General Method
Solubility in Oils Soluble General Method
Solubility in Dilute Acids Soluble (amine group protonated) General Method
pH (Saturated Solution, 25°C) Neutral – Slightly basic pH Meter
Flash Point Non-flammable Not applicable
Stability Stable under normal conditions; light-sensitive  

SECTION 3: CHEMICAL PROPERTIES AND REACTIVITY

Parameter Information
Chemical Character Ester-type local anesthetic; weak base (aromatic amine pKa ~2.5)
Stability Stable under normal conditions; light-sensitive
Hydrolysis Hydrolyzed at alkaline pH and by plasma esterases → para-aminobenzoic acid (PABA) + ethanol
Decomposition Products (Heating) Decomposes at 172°C; CO, CO2, NOx
Incompatible Materials Strong oxidizing agents, strong alkalis, silver nitrate, mercury salts
Reaction with Acids Soluble in dilute acids due to protonation of amine group
Light Sensitivity Slowly yellows upon exposure to light
Hazardous Polymerization Does not occur

SECTION 4: LOCAL ANESTHETICS COMPARISON

Property Benzocaine Lidocaine Procaine Tetracaine Bupivacaine
CAS Number 94-09-7 137-58-6 59-46-1 94-24-6 38396-39-3
Class Ester Amide Ester Ester Amide
Onset of Action Fast (topical) Fast (2-5 min) Moderate (5-10 min) Slow (5-10 min) Slow (5-10 min)
Duration of Action Short-Medium Medium (1-2 hrs) Short (30-60 min) Long (2-3 hrs) Long (3-8 hrs)
pKa 2.5 7.9 8.9 8.5 8.1
Water Solubility Slightly soluble Practically insoluble Very soluble (HCl) Slightly soluble Slightly soluble
Route Topical only Injection, topical Injection, topical Injection, topical Injection
Injectable Not suitable Yes Yes Yes Yes
Vasodilation None (exception) Yes Yes Yes Yes
Maximum Dose Topical limited 4.5 mg/kg 10 mg/kg 1.5 mg/kg 2 mg/kg
Allergy Risk Low Very Low Moderate (PABA) Moderate (PABA) Very Low

SECTION 5: PHARMACOLOGICAL PROPERTIES AND MECHANISM OF ACTION

Property Description
Mechanism of Action Blocks voltage-gated sodium (Na+) channels; prevents action potential generation and conduction in nerve cells
Anesthetic Class Ester-type local anesthetic (PABA ester)
Onset of Action Fast (30 seconds – 2 minutes for topical application)
Duration of Action Short-Medium (15-45 minutes); varies depending on formulation
Vasodilator Effect None (exception among local anesthetics); does not require epinephrine
Absorption Absorbed from mucosa and damaged skin; minimal absorption through intact skin
Metabolism Hydrolyzed by plasma pseudocholinesterases and liver esterases → PABA + ethanol
PABA Formation Hydrolysis releases para-aminobenzoic acid (PABA)
Injectable Use Not suitable for injection due to very low water solubility; topical use only
Methemoglobinemia Risk May cause methemoglobinemia at high doses or when applied to large surfaces (especially in children)

SECTION 6: PRIMARY APPLICATION AREAS

Sector / Application Use Typical Concentration
Oral Care / Dental Toothache, teething, oral ulcers, denture irritation 5 – 20% gel/cream/lozenge
Throat Lozenges Sore throat, pharyngitis, cough 5 – 10%
Dermatological Itching, insect bites, sunburn, minor burns, skin irritation 5 – 20% cream/gel/spray
Hemorrhoid Treatment Hemorrhoid pain and itching 5 – 20% ointment
Ear Drops Ear pain (otitis media, otitis externa) 5 – 10%
Cosmetic Laser hair removal, tattoo removal, pre-filler topical anesthesia 5 – 20% cream
Veterinary Superficial anesthetic (skin, mucosa) 5 – 10%
Medical Devices Lubricating and anesthetic gel for endoscopy, intubation tubes 2 – 10%

SECTION 7: QUALITY SPECIFICATIONS (PHARMACEUTICAL GRADE - USP/EP)

Parameter Specification Test Method
Appearance White crystalline powder Visual
Odor Odorless Olfactometric
Purity (C9H11NO2, Dry Basis) 98.0 – 102.0% HPLC / Titrimetric
Melting Range 88 – 90°C DSC / Capillary Tube
Loss on Drying (105°C, 2 hours) ≤ 0.5% Gravimetric
pH (Saturated Solution) Neutral – Slightly basic pH Meter
Chloride (Cl-) ≤ 0.01% Argentometric
Sulfate (SO4 2-) ≤ 0.02% Turbidimetric
Sulfated Ash ≤ 0.1% Gravimetric
Heavy Metals (as Pb) ≤ 10 ppm ICP-MS / USP <231>
Lead (Pb) ≤ 3 ppm ICP-MS
Arsenic (As) ≤ 1 ppm ICP-MS
Mercury (Hg) ≤ 1 ppm ICP-MS
Cadmium (Cd) ≤ 1 ppm ICP-MS
4-Aminobenzoic Acid (PABA) ≤ 0.5% HPLC
Related Substances (Total) ≤ 1.0% HPLC
Water Insoluble Matter ≥ 99.0% Gravimetric
Total Microbial Count ≤ 100 CFU/g USP <61>
Yeast and Mold ≤ 10 CFU/g USP <61>
E. coli Negative in 1g USP <62>
Salmonella spp. Negative in 25g USP <62>

SECTION 8: TOXICOLOGICAL PROFILE

Parameter Value
Acute Oral Toxicity (LD50, Rat) ~3,042 mg/kg
Acute Dermal Toxicity (LD50, Rabbit) > 2,000 mg/kg
Skin Irritation Mild irritant
Eye Irritation Irritant
Respiratory Irritation Inhalation of dust may cause mechanical irritation
Skin Sensitization Low risk; cross-allergy (PABA)
Carcinogenicity Not classified (IARC, NTP)
Mutagenicity Negative in in vitro tests
Reproductive Toxicity Limited data; use with caution at high doses
Methemoglobinemia Risk at high doses or when applied to large surfaces (especially in children)
Allergenicity Low-Moderate risk (PABA metabolite)

SECTION 9: GHS CLASSIFICATION AND LABELING

GHS Classification (compliant with 1272/2008/EC):

Hazard Class Category H-Statement
Skin Irritation Category 2 H315
Eye Irritation Category 2 H319
Specific Target Organ Toxicity (STOT - SE) Category 3 H335

Signal Word: WARNING

Hazard Pictograms: GHS07 (Exclamation Mark)

Hazard Statements (H-Codes):

Code Statement
H315 Causes skin irritation
H319 Causes serious eye irritation
H335 May cause respiratory irritation

Precautionary Statements (P-Codes):

Code Statement
P261 Avoid breathing dust
P280 Wear protective gloves/eye protection
P302+P352 IF ON SKIN: Wash with plenty of water and soap
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes
P312 Call a POISON CENTER/doctor if you feel unwell

SECTION 10: FIRST AID MEASURES

Exposure Route Action to Take
Inhalation Move to fresh air. Seek medical attention if respiratory irritation persists.
Skin Contact Wash with plenty of water and soap for at least 15 minutes. Seek medical attention if irritation persists.
Eye Contact Rinse immediately with plenty of water for at least 15 minutes. Remove contact lenses if present. Seek medical attention.
Ingestion Rinse mouth with water. If conscious, give 1-2 glasses of water. Do NOT induce vomiting. Seek medical attention.

SECTION 11: FIREFIGHTING MEASURES

Parameter Information
Fire Hazard Non-flammable
Hazards During Fire Decomposes above 172°C; CO, CO2, NOx
Suitable Extinguishing Media Water mist, CO2, dry chemical powder, foam
Special Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing

SECTION 12: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Cool (15-25°C), dry, well-ventilated area; light-protected closed packaging
Container Requirements Tightly closed, light-resistant containers
Keep Away From Light, moisture, alkaline substances, strong oxidizing agents
Shelf Life 48 months (unopened original packaging under appropriate storage conditions)
Stability Note Light-sensitive; hydrolyzes at alkaline pH; store in dry and dark environment

SECTION 13: PACKAGING OPTIONS

Packaging Type Quantity Material
Aluminum foil pouch (light-protective) 1 kg Laminated aluminum
Aluminum foil pouch (light-protective) 5 kg Laminated aluminum
Fiber drum with PE liner 25 kg Fiberboard + PE
HDPE drum (light-protected) 25-50 kg HDPE

SECTION 14: TRANSPORTATION INFORMATION

Parameter Information
UN Number Not regulated (not hazardous)
Hazard Class Not applicable
Packing Group Not applicable
ADR/RID Not regulated
IMDG Code Not regulated
IATA (Air) Not regulated
Marine Pollutant No
Transport Temperature Ambient

SECTION 15: REGULATORY STATUS

Region / Authority Status
USA (USP-NF) Official monograph (USP Benzocaine)
European Pharmacopoeia Official monograph (Ph. Eur. Benzocaine)
USA (FDA) OTC topical anesthetic; available without prescription
WHO Essential Medicines List Essential medicine (topical anesthetic)
Turkey Licensed pharmaceutical active ingredient; used in OTC products

SECTION 16: OTHER NAMES AND SYNONYMS

Type Name
Chemical Names Ethyl 4-Aminobenzoate; 4-Aminobenzoic Acid Ethyl Ester; p-Aminobenzoic Acid Ethyl Ester
Common Names Benzocaine, Ethyl Aminobenzoate
Other Names Anaesthesin, Anesthone
Trade Names Anbesol, Orajel, Lanacane, Solarcaine, Dermoplast
CAS Number 94-09-7
EC Number 202-303-5

SECTION 17: SUMMARY TABLE

Parameter Value
Product Benzocaine
CAS Number 94-09-7
Molecular Formula C9H11NO2
Molecular Weight 165.19 g/mol
Appearance White crystalline powder
Melting Point 88 – 90°C
pKa ~2.5
Solubility in Water Slightly soluble (~1.3 g/L)
Primary Function Ester-type topical local anesthetic
Shelf Life 48 months
GHS Signal Word Warning

SECTION 18: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

  1. Topical Use Only: Not suitable for injection due to very low water solubility; must be used topically only.

  2. Methemoglobinemia Risk: May cause methemoglobinemia at high doses or when applied to large surfaces, especially in children. Do not exceed recommended dose.

  3. Light Sensitivity: Slowly yellows upon exposure to light; store in light-resistant containers.

  4. Alkaline pH Hydrolysis: Hydrolyzes in alkaline environments; formulate at neutral or slightly acidic pH.

  5. PABA Allergy: May cause allergic reactions in patients sensitive to PABA and ester-type anesthetics.

BEST PRACTICE RECOMMENDATIONS:

  1. Formulation: Due to low water solubility, formulate as cream, gel, ointment, or spray; use appropriate solvents (ethanol, propylene glycol, oils).

  2. Dose Control: Limit total dose, especially in children and large surface applications.

  3. Storage: Store in dry, cool, and dark environment in tightly closed containers.

  4. Combination: Can be combined with other local anesthetics (lidocaine, tetracaine) to increase duration and depth of action.

  5. Allergy Testing: Prefer alternative (amide-type) anesthetic before use in patients with PABA sensitivity.

LEGAL DISCLAIMER:

The information provided in this document is presented in good faith based on our current knowledge and experience; however, since all usage conditions are beyond our control, it does not constitute a binding specification or warranty. This Technical Data Sheet is for informational purposes only and does not constitute medical advice. Users are obligated to test the suitability for their own applications. For complete safety, storage, handling, transportation, disposal, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. This product is not intended to diagnose, treat, cure, or prevent any disease.

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