Benzocaine

Modify Date: 2024-01-02 11:27:15

Benzocaine Structure
Benzocaine structure
Common Name Benzocaine
CAS Number 94-09-7 Molecular Weight 165.189
Density 1.1±0.1 g/cm3 Boiling Point 310.7±15.0 °C at 760 mmHg
Molecular Formula C9H11NO2 Melting Point 88-90 °C
MSDS Chinese USA Flash Point 164.2±17.9 °C

 Use of Benzocaine


Benzocaine shares a common receptor with all other local anesthetics (LAs) in the voltage-gated Na+ channel, with an IC50 of 0.8 mM tested with a potential of +30 mV.

 Names

Name benzocaine
Synonym More Synonyms

 Benzocaine Biological Activity

Description Benzocaine shares a common receptor with all other local anesthetics (LAs) in the voltage-gated Na+ channel, with an IC50 of 0.8 mM tested with a potential of +30 mV.
Related Catalog
Target

IC50: 0.8 mM (Na+ channel)[1].

In Vitro Benzocaine blocks μ1 wild-type Na+ currents in a dose-dependent Manner. The Benzocaine concentration that inhibits 50% of Na+ currents (IC50) is estimated to be about 0.8 mM when a test potential of +30 mV is applied. The slope of the h∞ curve is also significantly reduced by benzocaine (from 6.6 to 9.9 mV). Mutation of μ1-N1584A also significantly increases the potency of Benzocaine. At 1 mM, Benzocaine blocks about 55% of wild-type Na+ current but about 95% of μ1-N1584A mutant current. Benzocaine also appears to bind more strongly to its LA receptor in the N1584A mutant than in the wild type[1]. The inhibition of Ca2+ uptake occurres at lower Benzocaine concentration (IC50=40.3±1.2mM) than that affecting the enzymatic activity[2].
In Vivo A common Benzocaine-containing anesthetic is topically applied to the following species: dogs, domestic shorthair cats, Long-Evans rats, Sprague-Dawley rats, ferrets, rhesus monkeys, cynomolgus monkeys, owl monkeys, New Zealand White rabbits, miniature pigs, ICR mice, C3H mice, and C57BL/10SnJ mice. All animals, except mice and rats, receive a 2-second spray to the mucous membranes of the nasopharynx for an estimated dose of 56 mg. A 2-second spray to rodents' oral mucous membranes delivers too great a volume of fluid for these animals. The study is repeated in dogs several months later to confirm low response. Response to Benzocaine spray is observed in most animals tested, with response peaking between 15 and 30 minutes after dosing[3].
References

[1]. Wang GK et al. A common local anesthetic receptor for benzocaine and etidocaine in voltage-gated mu1 Na+ channels. Pflugers Arch. 1998 Jan;435(2):293-302.

[2]. Di Croce D et al. Drug action of benzocaine on the sarcoplasmic reticulum Ca-ATPase from fast-twitch skeletal muscle. Naunyn Schmiedebergs Arch Pharmacol. 2015 Nov;388(11):1163-70.

[3]. Davis JA, et al. Benzocaine-induced methemoglobinemia attributed to topical application of the anesthetic in several laboratory animal species. Am J Vet Res. 1993 Aug;54(8):1322-6.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 310.7±15.0 °C at 760 mmHg
Melting Point 88-90 °C
Molecular Formula C9H11NO2
Molecular Weight 165.189
Flash Point 164.2±17.9 °C
Exact Mass 165.078979
PSA 52.32000
LogP 1.95
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.555
Storage condition 0-6°C
Stability Stable. Combustible. Incompatible with strong oxidizing agents.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DG2450000
CHEMICAL NAME :
Benzoic acid, p-amino-, ethyl ester
CAS REGISTRY NUMBER :
94-09-7
BEILSTEIN REFERENCE NO. :
0638434
LAST UPDATED :
199706
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C9-H11-N-O2
MOLECULAR WEIGHT :
165.21
WISWESSER LINE NOTATION :
ZR DVO2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
REFERENCE :
JSCCA5 Journal of the Society of Cosmetic Chemists. (Soc. of Cosmetic Chemists, 1995 Broadway, Suite 1701, New York, NY 10023) V.1- 1947- Volume(issue)/page/year: 28,357,1977 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Blood - methemoglobinemia-carboxyhemoglobin
REFERENCE :
NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 263,454,1960
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3042 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis
REFERENCE :
TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (2),34,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis
REFERENCE :
TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (2),34,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
216 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 17,900,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,33,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - wild bird species
DOSE/DURATION :
56 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 21,315,1972 *** REVIEWS *** TOXICOLOGY REVIEW PHREA7 Physiological Reviews. (American Physiological Soc., 9650 Rockville Pike, Bethesda, MD 20814) V.1- 1921- Volume(issue)/page/year: 12,190,1932 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81723 No. of Facilities: 293 (estimated) No. of Industries: 8 No. of Occupations: 7 No. of Employees: 2005 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81723 No. of Facilities: 1499 (estimated) No. of Industries: 12 No. of Occupations: 17 No. of Employees: 167623 (estimated) No. of Female Employees: 146838 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi:Irritant
Risk Phrases R36/37/38;R43
Safety Phrases 22-24/25-37/39-26-24
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS DG2450000
Packaging Group III
HS Code 2922499990

 Synthetic Route

 Customs

HS Code 2922499990
Summary HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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 Synonyms

ORTHESIN
Americaine
Ora-jel
ethyl 4-aminobenzene carboxylate
Anaesthesin
AETHOFORM
Benzocainum
Ethyl 4-aminobenzoate
ethyl ester of p-aminobenzoic acid
Benzocaine
Ethoform
4-Aminobenzoic acid ethyl ester
Topcaine
Benzoic acid, 4-amino-, ethyl ester
Solu H
MFCD00007892
Euphagin
EINECS 202-303-5
4-ethoxycarbonylaniline
Norcaine
4-amino-benzoic acid ethyl ester
Norcain
Anaesthin
Anbesol
ethyl 4-amino-benzoate
p-aminobenzoic acid ethyl ester
Ethyl4-aminobenzoate
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