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137-58-6

137-58-6 structure
137-58-6 structure
  • Name: Lidocaine
  • Chemical Name: lidocaine
  • CAS Number: 137-58-6
  • Molecular Formula: C14H22N2O
  • Molecular Weight: 234.337
  • Catalog: API Anesthetic Agents Local anesthetics
  • Create Date: 2018-02-05 08:00:00
  • Modify Date: 2024-01-02 09:12:38
  • 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).
Name lidocaine
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
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
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.
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
Storage condition Store at RT
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility practically insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AN7525000
CHEMICAL NAME :
2',6'-Acetoxylidide, 2-(diethylamino)-
CAS REGISTRY NUMBER :
137-58-6
BEILSTEIN REFERENCE NO. :
2215784
LAST UPDATED :
199701
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C14-H22-N2-O
MOLECULAR WEIGHT :
234.38
WISWESSER LINE NOTATION :
2N2&1VMR B1 F1

HEALTH HAZARD DATA

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)
Symbol GHS07
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
109-89-7 structure

109-89-7

1131-01-7 structure

1131-01-7

~%

137-58-6 structure

137-58-6

Literature: Arkiv foer Kemi, , vol. 22A, # 18 p. 11
87-62-7 structure

87-62-7

~%

137-58-6 structure

137-58-6

Literature: Arkiv foer Kemi, , vol. 22A, # 18 p. 11
178421-96-0 structure

178421-96-0

~%

137-58-6 structure

137-58-6

51166-71-3 structure

51166-71-3

Literature: Langmuir, , vol. 26, # 13 p. 10561 - 10571
Total: 1 Page
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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