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Substance Name: Procaine [INN:BAN]
RN: 59-46-1
UNII: 4Z8Y51M438
InChIKey: MFDFERRIHVXMIY-UHFFFAOYSA-N

Note

  • A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).

Molecular Formula

  • C13-H20-N2-O2

Molecular Weight

  • 236.313
 

Classification Codes

  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Peripheral Nervous System Agents
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Procaine
  • Procaine [INN:BAN]

MeSH Heading

  • Procaine

Synonyms

  • 2-Diethylaminoethyl 4-aminobenzoate
  • 2-Diethylaminoethyl p-aminobenzoate
  • 2-Diethylaminoethylester kyseliny p-aminobenzoove
  • 2-Diethylaminoethylester kyseliny p-aminobenzoove [Czech]
  • 4-14-00-01138 (Beilstein Handbook Reference)
  • 4-Aminobenzoesaeure-beta-diethylaminoethylester
  • 4-Aminobenzoic acid diethylaminoethyl ester
  • Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester
  • Benzoic acid, p-amino-, 2-(diethylamino)ethyl ester
  • beta-Diethylaminoethyl 4-aminobenzoate
  • BRN 0913480
  • Diethylaminoethyl p-aminobenzoate
  • Duracaine
  • EINECS 200-426-9
  • Factor H3
  • HSDB 3388
  • Nissocaine
  • NSC 169497
  • p-Aminobenzoic acid 2-diethylaminoethyl ester
  • p-Aminobenzoyldiethylaminoethanol
  • Procain
  • Procaina
  • Procaina [INN-Spanish]
  • Procaine
  • Procaine, base
  • Procainum
  • Procainum [INN-Latin]
  • Spinocaine
  • Stoff H3
  • UNII-4Z8Y51M438
  • Vitamin H3

Systematic Names

  • Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester
  • Benzoic acid, p-amino-, 2-(diethylamino)ethyl ester
  • Procaine

Registry Numbers

CAS Registry Number

  • 59-46-1

FDA UNII

  • 4Z8Y51M438

Other Registry Number

  • 91484-72-9

System Generated Number

  • 0000059461

Structure Descriptors

InChI

1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3

InChIKey

MFDFERRIHVXMIY-UHFFFAOYSA-N

Smiles

c1(C(OCCN(CC)CC)=O)ccc(N)cc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 21500ug/kg (21.5mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
cat LDLo subcutaneous 225mg/kg (225mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
dog LDLo intraperitoneal 143mg/kg (143mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
dog LDLo subcutaneous 25mg/kg (25mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
frog LDLo intraspinal 220mg/kg (220mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 45, Pg. 291, 1932.
frog LDLo subcutaneous 600mg/kg (600mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: GENERAL ANESTHETIC
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 197, 1929.
guinea pig LDLo intraperitoneal 600mg/kg (600mg/kg)   Physiological Reviews. Vol. 12, Pg. 190, 1932.
guinea pig LDLo intravenous 50mg/kg (50mg/kg)   Physiological Reviews. Vol. 12, Pg. 190, 1932.
guinea pig LDLo parenteral 50mg/kg (50mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
guinea pig LDLo subcutaneous 400mg/kg (400mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 197, 1929.
man LDLo oral 147mg/kg (147mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 124mg/kg (124mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 213, 1970.
mouse LD50 intravenous 45mg/kg (45mg/kg) PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 382, 1956.
mouse LD50 oral 350mg/kg (350mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 subcutaneous 180mg/kg (180mg/kg)   Farmakologiya i Toksikologiya Vol. 29, Pg. 425, 1966.
mouse LD50 unreported 530mg/kg (530mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
rabbit LD50 intravenous 41mg/kg (41mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 37, 1952.
rabbit LDLo intraspinal 18mg/kg (18mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 137, 1935.
rabbit LDLo subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
rat LD50 intraperitoneal 260mg/kg (260mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
rat LD50 intravenous 42mg/kg (42mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
rat LD50 subcutaneous 600mg/kg (600mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 104, Pg. 388, 1956.
women TDLo intramuscular 1600ug/kg (1.6mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: STIFFNESS

BEHAVIORAL: REGIDITY
Journal of Neurology, Neurosurgery and Psychiatry. Vol. 34, Pg. 20, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 61 deg C   EXP
pKa Dissociation Constant 8.05 (none) 15 EXP
log P (octanol-water) 2.14 (none)   EXP
Water Solubility 9450 mg/L 30 EXP
Vapor Pressure 2.03E-05 mm Hg 25 EST
Henry's Law Constant 1.42E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.31E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.