CAS 137-58-6|Lidocaine
Introduction：Basic information about CAS 137-58-6|Lidocaine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Lidocaine | ||
|---|---|---|---|
| CAS Number | 137-58-6 | Molecular Weight | 234.337 |
| Density | 1.0±0.1 g/cm3 | Boiling Point | 372.7±52.0 °C at 760 mmHg |
| Molecular Formula | C14H22N2O | Melting Point | 66-69°C |
| MSDS | ChineseUSA | Flash Point | 179.2±30.7 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | lidocaine |
|---|---|
| Synonym | More Synonyms |
Lidocaine BiologicalActivity
| Description | Lidocaine, an amide local anesthetic, has anti-inflammatory properties in vitro and in vivo, possibly due to an attenuation of pro-inflammatory cytokines, intracellular adhesion molecule-1 (ICAM-1), and reduction of neutrophils influx.Target: Lidocaine is a common local anesthetic and antiarrhythmic drug. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery. Lidocaine, the first amino amide–type local anesthetic, was first synthesized under the name xylocaine by Swedish chemist Nils Lofgren in 1943. His colleague Bengt Lundqvist performed the first injection anesthesia experiments on himself.Lidocaine is approximately 95% metabolized (dealkylated) in the liver by CYP3A4 to the pharmacologically-active metabolites monoethylglycinexylidide (MEGX) and then subsequently to the inactive glycine xylidide. MEGX has a longer half life than lidocaine but also is a less potent sodium channel blocker. The elimination half-life of lidocaine is approximately 90–120 minutes in most patients. This may be prolonged in patients with hepatic impairment (average 343 minutes) or congestive heart failure (average 136 minutes). |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>Sodium ChannelResearch Areas >>Cardiovascular Disease |
| References | [1]. VAN DER Wal S, et al. Lidocaine increases the anti-inflammatory cytokine IL-10 following mechanical ventilation in healthy mice. Acta Anaesthesiol Scand. 2014 Oct 14. [2]. Acevedo-Arcique CM, et al. Lidocaine, dexmedetomidine and their combination reduce isoflurane minimum alveolar concentration in dogs. PLoS One. 2014 Sep 18;9(9):e106620. |
Chemical & Physical Properties
| Density | 1.0±0.1 g/cm3 |
|---|---|
| Boiling Point | 372.7±52.0 °C at 760 mmHg |
| Melting Point | 66-69°C |
| Molecular Formula | C14H22N2O |
| Molecular Weight | 234.337 |
| Flash Point | 179.2±30.7 °C |
| Exact Mass | 234.173218 |
| PSA | 32.34000 |
| LogP | 3.63 |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.512 |
| InChIKey | NNJVILVZKWQKPM-UHFFFAOYSA-N |
| SMILES | CCN(CC)CC(=O)Nc1c(C)cccc1C |
| Storage condition | Store at RT |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Water Solubility | practically insoluble |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraspinal
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 1 mL/kg
- TOXIC EFFECTS :
- Behavioral - euphoria Behavioral - hallucinations, distorted perceptions
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 21 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 39 mg/kg
- TOXIC EFFECTS :
- Behavioral - hallucinations, distorted perceptions Behavioral - excitement Cardiac - change in rate
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 300 mg/kg/5D-I
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section Nutritional and Gross Metabolic - body temperature increase
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 16 mg/kg
- TOXIC EFFECTS :
- Cardiac - change in rate Lungs, Thorax, or Respiration - dyspnea
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 8643 ug/kg/4H-C
- TOXIC EFFECTS :
- Behavioral - toxic psychosis
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 23 mg/kg
- TOXIC EFFECTS :
- Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 1700 ug/kg/2M-C
- TOXIC EFFECTS :
- Behavioral - coma Cardiac - pulse rate Lungs, Thorax, or Respiration - respiratory depression
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 317 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 133 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 335 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 18 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 39400 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 220 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy) Lungs, Thorax, or Respiration - respiratory stimulation
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 102 mg/kg
- TOXIC EFFECTS :
- Peripheral Nerve and Sensation - local anesthetic Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 238 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 20 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - other changes
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 41 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 120 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 65 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Parenteral
- DOSE :
- 540 ug/kg
- SEX/DURATION :
- female 39 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intramuscular
- DOSE :
- 6 mg/kg
- SEX/DURATION :
- female 11 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - behavioral
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Parenteral
- DOSE :
- 6 mg/kg
- SEX/DURATION :
- female 11 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - sex ratio
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Parenteral
- DOSE :
- 6 mg/kg
- SEX/DURATION :
- female 18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - behavioral
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Implant
- DOSE :
- 7500 mg/kg
- SEX/DURATION :
- female 3-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
MUTATION DATA - TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Bacteria - Salmonella typhimurium
- DOSE/DURATION :
- 50 umol/plate
- REFERENCE :
- JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 34,157,1986 *** REVIEWS *** TOXICOLOGY REVIEW BNYMAM Bulletin of the New York Academy of Medicine. (New York Academy of Medicine, 2 E. 103rd St., New York, NY 10029) Ser 2: V.1- 1925- Volume(issue)/page/year: 52,222,1976 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84482 No. of Facilities: 443 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 5743 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84482 No. of Facilities: 763 (estimated) No. of Industries: 1 No. of Occupations: 15 No. of Employees: 51880 (estimated) No. of Female Employees: 43813 (estimated)
- TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Bacteria - Salmonella typhimurium
- DOSE/DURATION :
- 50 umol/plate
- REFERENCE :
- JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 34,157,1986 *** REVIEWS *** TOXICOLOGY REVIEW BNYMAM Bulletin of the New York Academy of Medicine. (New York Academy of Medicine, 2 E. 103rd St., New York, NY 10029) Ser 2: V.1- 1925- Volume(issue)/page/year: 52,222,1976 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84482 No. of Facilities: 443 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 5743 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84482 No. of Facilities: 763 (estimated) No. of Industries: 1 No. of Occupations: 15 No. of Employees: 51880 (estimated) No. of Female Employees: 43813 (estimated)
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 |
| Precautionary Statements | P301 + P312 + P330 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Faceshields;Gloves |
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R22 |
| Safety Phrases | S22-S26-S36 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| RTECS | AN7525000 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
| HS Code | 2924299090 |
Customs
| HS Code | 2924299090 |
|---|---|
| Summary | 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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Synonyms
| 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide |
| Lignocaine |
| 4,4'-DIMETHOXY DIPHENYL SULFOXIDE LIDOCAINE-D6 |
| 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide,Lignocaine,Xylocaine |
| Maricaine |
| MFCD08443609 |
| Gravocain |
| 2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide |
| Lidoderm |
| N1-(2,6-dimethylphenyl)-2-(diethylamino)acetamide |
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide |
| XYLOCAINE |
| N-(2,6-Dimethylphenyl)-N,N-diethylglycinamide |
| 2-Diethylamino-2',6'-acetoxylidide |
| N-(2,6-Diméthylphényl)-N,N-diéthylglycinamide |
| Anestacon |
| L-Caine |
| Leostesin |
| Esracaine |
| Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- |
| Lidothesin |
| 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide Lignocaine Xylocaine |
| N-(2,6-dimethylphenyl)-N2,N2-diethylglycinamide |
| lignocainum hydrochloricum |
| Lidocaine |
| w-Diethylamino-2,6-dimethylacetanilide |
| EINECS 205-302-8 |
