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Procaine ( CASNO:59-46-1 )

Identification and Related Records
Name:
Procaine
CAS Registry number:
59-46-1
Synonyms:
Benzoicacid, p-amino-, 2-(diethylamino)ethyl ester (8CI)
2-(Diethylamino)ethylp-aminobenzoate
2-Diethylaminoethyl 4-aminobenzoate
4-Aminobenzoic acid2-(diethylamino)ethyl ester
4-Aminobenzoic acid diethylaminoethyl ester
Diethylaminoethyl p-aminobenzoate
Duracaine
Nissocaine
PfizerpenAS
Procain
Procaine base
SP 01
Spinocaine
Vitamin H3
p-Aminobenzoic acid 2-diethylaminoethyl ester
b-(Diethylamino)ethyl p-aminobenzoate
b-Diethylaminoethyl4-aminobenzoate
EINECS(EC#):
200-426-9
Molecular Formula:
C13H20N2O2
Molecular Weight:
236.31
Inchi:
InChI=1/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
Canonical SMILES:
CCN(CC)CCOC(=O)C1=CC=C(C=C1)N
Chemical and Physical Properties
Density:
1.077g/cm3
Melting Point:
61 deg C
Boiling Point:
373.6 °C at 760 mmHg
Refractive Index:
1.542
Flash Point:
179.8 °C
Solubilities:
Sol in alcohol, ether, benzene, chloroform
Soluble in ethanol, ethyl ether, and benzene
In water, 9.45X10+3 mg/l @ 30 deg C
Color/Form:
Anhydrous plates, tables from ligroin or ether
Spectral properties:
MAX ABSORPTION (WATER): 221 NM (LOG E= 3.90); 290 (LOG E= 4.23)
IR: 7605 (Sadtler Research Laboratories Prism Collection)
UV: 2131 (Sadtler Research Laboratories Spectral Collection)
NMR: 302 (Varian Associates NMR Spectra Catalogue)
MASS: 2-634 (Archives of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 86 m/z, 99 m/z, 120 m/z, 164 m/z
Computed Properties:
Molecular Weight:236.3101 [g/mol]
Molecular Formula:C13H20N2O2
XLogP3:1.9
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:7
Tautomer Count:3
Exact Mass:236.152478
MonoIsotopic Mass:236.152478
Topological Polar Surface Area:55.6
Heavy Atom Count:17
Formal Charge:0
Complexity:222
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:2
Feature 3D Ring Count:1
Effective Rotor Count:7
Conformer Sampling RMSD:0.8
CID Conformer Count:71
Safety and Handling
HazardClass:
6.1(b)
Safety:
Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by parenteral route. Human systemic effects by intramuscular route: lack of muscular control, rigidity, and possibly catalepsy. See also ESTERS. When heated to decomposition it emits toxic fumes of NOx. Used as a local anesthetic.
RIDADR: 3249
HazardClass: 6.1(b)
PackingGroup: III
PackingGroup:
III
Transport:
3249
Formulations/Preparations:
IT IS AVAIL AS OFFICIAL INJECTION. MARKET PREPN INCL FOLLOWING: AMPULS OR VIALS OF 0.5, 1, 2, OR 10% SOLN WITHOUT EPINEPHRINE, OR 1 OR 2% SOLN WITH EPINEPHRINE IN CONCN OF 1:50,000-1:100,000, FOR INFILTRATION & NERVE BLOCK; 5-20% SOLN IN AMPULS, FOR SPINAL ANESTHESIA ... /HYDROCHLORIDE/
... AMPULS OF STERILE PROCAINE HYDROCHLORIDE CRYSTALS (50-500 MG), FOR SPINAL ANESTHESIA; 0.1 OR 0.2% PROCAINE HYDROCHLORIDE IN ISOTONIC SODIUM CHLORIDE SOLN, FOR IV INFUSION. /HYDROCHLORIDE/
Grade: USP /Hydrochloride/
Exposure Standards and Regulations:
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Specification:
  Procaine , with CAS number of 59-46-1, can be called 2-(Diethylamino)ethyl 4-aminobenzoate ; 2-(Diethylamino)ethyl p-aminobenzoate ; 2-(Diethylamino)ethylp-aminobenzoate ; 2-Diethylaminoethyl4-aminobenzoate ; 2-Diethylaminoethylester kyseliny p-aminobenzoove ; 2-Diethylaminoethylesterkyselinyp-aminobenzoove ; 2-Diethylaminoethylp-aminobenzoate ; 4-Aminobenzoic acid diethylaminoethyl ester .
Octanol/Water Partition Coefficient:
log Kow= 1.92
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

USUALLY PREPD BY INTERACTION OF 2-DIETHYLAMINOETHANOL WITH P-NITROBENZOYL CHLORIDE, FOLLOWED BY REDUCTION OF 2-DIETHYLAMINOETHYL P-NITROBENZOATE, OR BY ESTERIFYING P-AMINOBENZOIC ACID WITH 2-DIETHYLAMINOETHANOL USING H2SO4 AS CATALYST: US PATENT 812,554 (1906).
Prepn: A. Einhorn, U.S pat 812,554 (1906); Idem, Ann. 371, 125 (1909); A. Einhorn, E. Uhlfelder, ibid. 131.
(1) By heating chloroethyl-p-nitrobenzoic ester with diethylamine for 24 hours under pressure at 120 deg C. The product is then reduced with tin and hydrochloric acid. (2) By condensation of ethylene chlorohydrin with diethylamine. The chloroethyldiethylamine formed is heated with sodium-p-aminobenzoate. /Hydrochloride/
Prepared by reacting benzocaine and 2-diethylaminoethanol in the presence of catalytic amounts of sodium and simultaneous removal of the nascent ethanol by distillation. /Hydrochloride/
Biomedical Effects and Toxicity
Pharmacological Action:
- Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
Therapeutic Uses:
Anesthetics, Local
PROCAINE SOLN ARE USED FOR INFILTRATION ANESTHESIA ..., NERVE BLOCK ..., & SPINAL ANESTHESIA (DOSE VARIES WITH TECHNIC EMPLOYED). FOR CONTINUAL CAUDAL ANALGESIA ... /HYDROCHLORIDE/
OBJECTIVE OF CONTINUOUS SPINAL ANESTHESIA IS TO ... PRODUCE LEVEL, DEGREE, & DURATION OF ANESTHESIA DESIRED. ... LOCAL ANESTHETIC OF SHORT DURATION, SUCH AS PROCAINE, CAN BE USED TO INCR CONTROLLABILITY FURTHER.
/Procaine hydrochloride/ is injected locally adjacent to the muscle cone ... or in the region of the facial nerve ... to reduce pain and to prevent eye and lid movements during surgery. ... Used to block nerve endings in the immediate area of surgery (infiltration anesthesia) for procedures such as minor lid operations. /Procaine hydrochloride/
PROCAINE CAN FORM POORLY SOL SALTS OR CONJUGATE WITH OTHER DRUGS & PROLONG THEIR ACTION. ... AFTER IM INJECTION OF PROCAINE PENICILLIN G, ANTIBIOTIC IS ABSORBED VERY SLOWLY SO THAT DETECTABLE CONCN OF PENICILLIN EXIST IN BLOOD & URINE FOR PROLONGED PERIODS ...
IT IS POSSIBLY EFFECTIVE FOR...ANTISPASMODIC, ANTIPRURITIC, & ANTIARRHYTHMIC ACTION. IT IS USUALLY EMPLOYED IN SOLN CONTAINING EPINEPHRINE, 1:50,000; ABSORPTION IS RETARDED...REMAINS IN CONTACT WITH NERVE FIBERS FOR LONGER...TIME, & DURATION OF ACTION IS MUCH PROLONGED. /HYDROCHLORIDE/
PROCAINE IN COMBINATION WITH BUTETHAMINE, TETRACAINE, OR PROPOXYCAINE & VASOCONSTRICTOR AGENT SUCH AS EPINEPHRINE, PHENYLEPHRINE, LEVARTERENOL, OR LEVONORDEFRIN IS USED AS LOCAL ANESTHETIC IN DENTISTRY.
PROCAINE IS NOT EFFICIENT LOCAL ANESTHETIC FOR TOPICAL APPLICATION TO MUCOUS MEMBRANES & IS SELDOM EMPLOYED AS SUCH, CONCN OF 10-20% BEING NECESSARY FOR ADEQUATE ANESTHESIA. /HYDROCHLORIDE/
... USUALLY INJECTED INTO SUBARACHNOID SPACE BETWEEN CONUS MEDULLARIS & TERMINAL PORTION OF SUBARACHNOID SPACE ... TO AVOID INJURY TO SPINAL CORD. ... UPWARD PASSAGE ... DEPENDS UPON ... POSITION OF PT, SPECIFIC GRAVITY OF INJECTED SOLN, NATURAL CURVATURE OF SPINE, MOVEMENTS ... BY PT, SIZE OF ... SPACE ... /LOCAL ANESTHETICS/
PROCAINE SUPPRESSES COUGH REFLEX, DECR LARYNGEAL IRRITABILITY & HAS GENERAL ANESTHETIC PROPERTIES. INFUSION WAS ADDED TO GENERAL ANESTHESIA AFTER ENDOTRACHEAL INTUBATION. EMERGENCE AVG 15 MIN IN STUDY GROUP COMPARED TO 36 MIN IN CONTROL GROUP; NO PROCAINE TOXICITY.
IN 74 PT PROCAINE HYDROCHLORIDE WAS SAFE ANESTHETIC ADJUVANT IN DOSES OF 1 MG/KG/MIN EVEN WHEN TOTAL DOSE WAS 5-7 G. BLOOD PRESSURE, HEART RATE, EKG VARIABLES & BLOOD GASES WERE NOT ADVERSELY AFFECTED. PT HAD NO NAUSEA OR ADVERSE POSTANESTHESIA SYMPTOMS.
Local infiltration: ... Procaine /is/ indicated. /Included in US product labeling/
Peripheral nerve block: ... Procaine /is/ indicated. /Included in US product labeling/
Retrobulbar block: ... Procaine ... /is/ indicated. /NOT included in US product labeling/
Biomedical Effects and Toxicity:
/PARA-AMINOBENZOIC ACID/ ... IS EXCRETED IN URINE TO EXTENT OF ABOUT 80%, EITHER UNCHANGED OR IN CONJUGATED FORM. ONLY 30% OF DIETHYLAMINOETHANOL CAN BE RECOVERED IN URINE; REMAINDER UNDERGOES METABOLIC DEGRADATION.
... IT HAS BEEN SHOWN THAT, FOLLOWING INTRODUCTION OF PROCAINE INTO EPIDURAL SPACE IN USUAL ANESTHETIC DOSE, SIGNIFICANT CONCN IS ACHIEVED IN SPINAL FLUID.
RATE OF ENZYMATIC HYDROLYSIS OF LOCAL ANESTHETIC AGENTS BY SPINAL FLUID IS SLOW. ... DURATION OF ANESTHESIA DEPENDS UPON RATE AT WHICH DRUG IS REMOVED FROM CSF & FROM NERVE ROOTS WHERE IT EXERTS ITS ACTION. /LOCAL ANESTHETICS/
ABSORPTION DOES NOT TAKE PLACE FROM STOMACH, ESOPHAGUS, OR BLADDER IF MUCOSA INTACT. /LOCAL ANESTHETICS/
SITE OF ACTION OF MINIMALLY EFFECTIVE CONCN OF PROCAINE, WHICH BLOCK SENSORY BUT NOT MOTOR IMPULSES, IS DORSAL ROOT GANGLIA. THUS, ONSET OF ANALGESIA FOLLOWING INTRATHECAL ADMIN OF LOCAL ANESTHETIC DRUG DEPENDS UPON PASSAGE OF DRUG FROM SPINAL FLUID INTO SPINAL NERVE ROOTS, GANGLIA, & POSSIBLY SPINAL CORD ITSELF.
DURATION OF ACTION OF LOCAL ANESTHETIC IS PROPORTIONAL TO TIME DURING WHICH IT IS IN ACTUAL CONTACT WITH NERVOUS TISSUES. CONSEQUENTLY, PROCEDURES THAT MAINTAIN LOCALIZATION OF DRUG AT NERVE GREATLY PROLONG PERIOD OF ANESTHESIA. /LOCAL ANESTHETICS/
MODEL FOR PROCAINE DISTRIBUTION IN HUMANS RELATES INDIVIDUAL CHARACTERISTICS TO GENERAL PARAMETERS TO PROVIDE INDIVIDUALIZED DISTRIBUTION PROFILE.
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