We unleash your business potential by maximize the business innovation.
Send EmailBupivacaine Hydrochloride, Bupivacaine HCl, Bupivacaine Base, 38396-39-3, 2180-92-9
BUPIVACAINE HYDROCHLORIDE
PRODUCT IDENTIFIER INFORMATION
| Parameter | Information |
|---|---|
| Product Name | Bupivacaine Hydrochloride |
| Chemical Name (IUPAC) | (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride |
| CAS Number | 38396-39-3 (HCl salt) / 2180-92-9 (Base) |
| EC Number (EINECS) | 253-912-7 |
| Molecular Formula (Base) | C18H28N2O |
| Molecular Formula (HCl Salt) | C18H29ClN2O |
| Molecular Weight (Base) | 288.43 g/mol |
| Molecular Weight (HCl Salt) | 324.89 g/mol |
SECTION 1: CHEMICAL IDENTITY AND DESCRIPTION
| Parameter | Information |
|---|---|
| Chemical Name (IUPAC) | (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride |
| Synonyms | Bupivacaine Hydrochloride, Bupivacaine HCl |
| Trade Names | Marcaine, Sensorcaine, Vivacaine, Exparel (liposomal form) |
| CAS Number (HCl Salt) | 38396-39-3 |
| CAS Number (Base) | 2180-92-9 |
| EC Number (EINECS) | 253-912-7 |
| Molecular Formula (Base) | C18H28N2O |
| Molecular Formula (HCl Salt) | C18H29ClN2O |
| Molecular Weight (Base) | 288.43 g/mol |
| Molecular Weight (HCl Salt) | 324.89 g/mol |
| Chemical Class | Amide-type local anesthetic |
| Chirality | Racemic mixture (R-(+)- and S-(-)-enantiomers) |
| Physical State (20°C) | Solid (white crystalline powder) |
| Odor | Odorless |
| Taste | Bitter; temporary numbness on tongue |
SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES
| Property | Value | Test Method |
|---|---|---|
| Appearance | White crystalline powder | Visual |
| Odor | Odorless | Olfactometric |
| Taste | Bitter; temporary numbness | Sensory |
| Molecular Weight (HCl Salt) | 324.89 g/mol | Calculated |
| Molecular Weight (Base) | 288.43 g/mol | Calculated |
| Melting Point (HCl Salt) | 250 – 260°C | DSC |
| Melting Point (Base) | 107 – 108°C | DSC |
| pKa (25°C) | ~8.1 | Potentiometric |
| Solubility in Water (HCl Salt) | Soluble (~50 g/L) | Gravimetric |
| Solubility in Ethanol | Soluble | General Method |
| Solubility in Chloroform | Soluble | General Method |
| pH (1% HCl salt solution, 25°C) | 4.0 – 6.0 | pH Meter |
| Partition Coefficient (Log P) | ~3.41 (base) | Calculated |
| Protein Binding | ~95% (primarily α1-acid glycoprotein) | - |
| Stability | Stable under normal conditions; light-sensitive |
SECTION 3: CHEMICAL PROPERTIES AND REACTIVITY
| Parameter | Information |
|---|---|
| Chemical Character | Amide-type local anesthetic; weak base (pKa ~8.1); lipophilic (Log P ~3.41) |
| Stability | Stable under normal conditions; light-sensitive; resistant to autoclave sterilization |
| Hydrolysis | Amide bond much more resistant to hydrolysis compared to ester-type anesthetics |
| Decomposition Products (Heating) | CO, CO2, NOx, HCl |
| Incompatible Materials | Strong oxidizing agents, strong alkalis |
| Reaction with Alkali | Free base precipitates |
| Hazardous Polymerization | Does not occur |
SECTION 4: LOCAL ANESTHETICS COMPARISON
| Property | Bupivacaine | Lidocaine | Procaine | Ropivacaine | Levobupivacaine |
|---|---|---|---|---|---|
| CAS Number | 38396-39-3 | 137-58-6 | 59-46-1 | 98717-15-8 | 27262-47-1 |
| Class | Amide | Amide | Ester | Amide | Amide (S-isomer) |
| Onset of Action | Slow (5-10 min) | Fast (2-5 min) | Moderate (5-10 min) | Slow (5-15 min) | Slow (5-10 min) |
| Duration of Action | Long (3-8 hrs) | Medium (1-2 hrs) | Short (30-60 min) | Long (3-6 hrs) | Long (3-8 hrs) |
| pKa | 8.1 | 7.9 | 8.9 | 8.1 | 8.1 |
| Maximum Dose | 2 mg/kg | 4.5 mg/kg | 10 mg/kg | 3 mg/kg | 2 mg/kg |
| Cardiotoxicity | High | Low | Low | Moderate | Low (S-isomer) |
| Sensory/Motor Separation | Poor | Moderate | Poor | Good | Good |
| Allergy Risk | Very Low | Very Low | Moderate (PABA) | Very Low | Very Low |
| Primary Use | Epidural, spinal, peripheral nerve block | Infiltration, topical | Infiltration (historical) | Epidural, spinal | Epidural, spinal |
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 | Amide-type local anesthetic (amino amide) |
| Onset of Action | Slow (5-10 minutes) |
| Duration of Action | Long (3-8 hours); up to 72 hours in liposomal form |
| Lipophilic Property | Highly lipophilic (Log P ~3.41); more lipophilic than lidocaine |
| Protein Binding | ~95% (primarily α1-acid glycoprotein) |
| Vasodilator Effect | Less vasodilation than lidocaine and procaine |
| Metabolism | Metabolized in liver by CYP3A4 and CYP2C9 enzymes; N-dealkylation |
| Half-Life | 2.7 hours (adults); 8 hours (neonates) |
| Cardiotoxicity | Cardiotoxic at high doses; slow dissociation from sodium channels (fast-in, slow-out) |
| Sensory/Motor Separation | Limited sensory-motor separation at low concentrations |
SECTION 6: PRIMARY APPLICATION AREAS
| Sector / Application | Use | Typical Concentration / Dose |
|---|---|---|
| Surgery - Epidural | Epidural anesthesia (surgical) | 0.5 – 0.75% |
| Surgery - Spinal | Spinal anesthesia | 0.5% (hyperbaric/isobaric) |
| Obstetrics - Epidural | Epidural analgesia (labor pain) | 0.0625 – 0.25% |
| Peripheral Nerve Block | Brachial plexus, femoral, sciatic nerve block | 0.25 – 0.5% |
| Post-operative Analgesia | Wound infiltration, nerve block | 0.25 – 0.5% |
| Chronic Pain Management | Trigeminal neuralgia, complex regional pain syndrome | 0.25 – 0.5% |
| Liposomal Bupivacaine (Exparel) | Post-operative analgesia (up to 72 hours) | 133-266 mg |
| Dentistry | Long-duration dental procedures | 0.5% (with epinephrine) |
| Veterinary | Local infiltration, nerve block | 0.25 – 0.5% |
SECTION 7: QUALITY SPECIFICATIONS (PHARMACEUTICAL GRADE - USP/EP)
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | White crystalline powder | Visual |
| Odor | Odorless | Olfactometric |
| Purity (C18H29ClN2O, Dry Basis) | 98.5 – 101.5% | HPLC / Titrimetric |
| Melting Range (HCl Salt) | 250 – 260°C | DSC / Capillary Tube |
| Loss on Drying (105°C, 2 hours) | ≤ 0.5% | Gravimetric |
| pH (1% solution, 25°C) | 4.0 – 6.0 | pH Meter |
| Chloride (Cl-) | 10.5 – 11.3% | Argentometric |
| Sulfated Ash | ≤ 0.1% | Gravimetric |
| Heavy Metals (as Pb) | ≤ 20 ppm | ICP-MS / USP <231> |
| Lead (Pb) | ≤ 3 ppm | ICP-MS |
| Arsenic (As) | ≤ 3 ppm | ICP-MS |
| Mercury (Hg) | ≤ 1 ppm | ICP-MS |
| Cadmium (Cd) | ≤ 1 ppm | ICP-MS |
| 2,6-Dimethylaniline | ≤ 100 ppm | HPLC |
| Related Substances (Total) | ≤ 1.0% | HPLC |
| Enantiomeric Purity (for Levobupivacaine) | S-isomer ≥ 99% | Chiral HPLC |
| 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) | ~200-400 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 |
| Carcinogenicity | Not classified (IARC, NTP) |
| Mutagenicity | Negative in in vitro tests |
| Reproductive Toxicity | Fetal effects at high doses; use with caution during pregnancy |
| Cardiotoxicity | Significantly cardiotoxic at high doses; ventricular arrhythmia, cardiac arrest |
| Neurotoxicity | At high doses: dizziness, tinnitus, convulsions, loss of consciousness |
| Systemic Toxicity | More toxic than lidocaine; narrow safety margin |
SECTION 9: GHS CLASSIFICATION AND LABELING
GHS Classification (compliant 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 |
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 |
| H331 | Toxic if inhaled |
Precautionary Statements (P-Codes):
| Code | Statement |
|---|---|
| P261 | Avoid breathing dust/fume/gas |
| P280 | Wear protective gloves/protective clothing/eye protection |
| P301+P310 | IF SWALLOWED: Immediately call a POISON CENTER/doctor |
| P302+P352 | IF ON SKIN: Wash with plenty of water and soap |
| P304+P340 | IF INHALED: Remove person to fresh air and keep comfortable for breathing |
| P311 | Call a POISON CENTER/doctor |
SECTION 10: FIRST AID MEASURES
| Exposure Route | Action to Take |
|---|---|
| Inhalation | Move to fresh air. Seek medical attention if breathing difficulty persists. |
| Skin Contact | Remove contaminated clothing immediately. Wash with plenty of water and soap for at least 15 minutes. Seek medical attention. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Remove contact lenses if present. Seek immediate medical attention. |
| Ingestion | Rinse mouth with water. Do NOT induce vomiting. Seek immediate medical attention and show container or label. |
SECTION 11: FIREFIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Non-flammable |
| Hazards During Fire | CO, CO2, NOx, HCl |
| 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 | Room temperature (15-25°C), dry, well-ventilated area; light-protected closed packaging |
| Container Requirements | Tightly closed, light-resistant containers |
| Keep Away From | Light, moisture, strong oxidizing agents, strong alkalis |
| Shelf Life | 36-48 months (unopened original packaging under appropriate storage conditions) |
| Stability Note | Resistant to autoclave sterilization; light-sensitive |
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 | UN 2811 (Toxic Solid, Organic, n.o.s.) |
| Hazard Class | 6.1 (Toxic Substances) |
| Packing Group | III |
| ADR/RID | UN 2811, Toxic Solid, 6.1, PG III |
| IMDG Code | UN 2811, Toxic Solid, 6.1, PG III |
| IATA (Air) | UN 2811, Toxic Solid, 6.1, PG III |
| Marine Pollutant | No |
| Transport Temperature | Ambient |
SECTION 15: REGULATORY STATUS
| Region / Authority | Status |
|---|---|
| USA (USP-NF) | Official monograph (USP Bupivacaine Hydrochloride) |
| European Pharmacopoeia | Official monograph (Ph. Eur. Bupivacaine Hydrochloride) |
| USA (FDA) | Prescription drug; liposomal form (Exparel) approved |
| WHO Essential Medicines List | Essential medicine (local anesthetic) |
| Turkey | Licensed pharmaceutical active ingredient; prescription drug |
| DEA / Controlled Substance | Not a controlled substance |
SECTION 16: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Chemical Names | (RS)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; 1-Butyl-2',6'-pipecoloxylidide |
| Common Names | Bupivacaine, Bupivacaine HCl |
| Trade Names | Marcaine, Sensorcaine, Vivacaine, Exparel (liposomal) |
| Isomeric Forms | Levobupivacaine (S-isomer, CAS 27262-47-1); Ropivacaine (S-isomer analog) |
| CAS Number (HCl Salt) | 38396-39-3 |
| CAS Number (Base) | 2180-92-9 |
| EC Number | 253-912-7 |
SECTION 17: SUMMARY TABLE
| Parameter | Value |
|---|---|
| Product | Bupivacaine Hydrochloride |
| CAS Number | 38396-39-3 |
| Molecular Formula (Base) | C18H28N2O |
| Molecular Weight (HCl Salt) | 324.89 g/mol |
| Appearance | White crystalline powder |
| Melting Point | 250 – 260°C |
| pKa | ~8.1 |
| Solubility in Water | ~50 g/L |
| Primary Function | Amide-type long-acting local anesthetic |
| Shelf Life | 36-48 months |
| GHS Signal Word | Danger |
| UN Number | UN 2811 (Toxic Solid, 6.1, PG III) |
SECTION 18: CRITICAL WARNINGS AND BEST PRACTICES
CRITICAL WARNINGS:
Cardiotoxicity: Bupivacaine is significantly more cardiotoxic than lidocaine and procaine. Absolutely avoid intravascular injection.
Narrow Safety Margin: Maximum dose 2 mg/kg; overdose may cause serious cardiac and neurological toxicity.
Toxic: Toxic if swallowed, in contact with skin, or if inhaled. Use protective equipment.
Epidural/Spinal Administration: Should only be administered by experienced clinicians.
Liposomal Form: Liposomal bupivacaine (Exparel) should not be administered simultaneously with free bupivacaine.
BEST PRACTICE RECOMMENDATIONS:
Aspiration: Always aspirate before injection; avoid intravascular injection.
Dose Calculation: Calculate maximum safe dose (2 mg/kg); adjust dose according to patient weight.
Test Dose: Administer test dose with epinephrine before epidural administration.
Cardiac Monitoring: Monitor ECG and vital signs during high-dose administration.
Levobupivacaine Alternative: S-isomer (levobupivacaine) may be preferred for lower cardiotoxicity risk.
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.