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Showing Compound Procaine (FDB029371)

Record Information
Version1.0
Creation date2011-09-21 01:54:46 UTC
Update date2018-05-29 01:54:44 UTC
Primary IDFDB029371
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProcaine
DescriptionProcaine is a local anesthetic drug of the amino ester group. It is used primarily to reduce the pain of intramuscular injection of penicillin, and it is also used in dentistry. Owing to the ubiquity of the trade name Novocain, procaine is sometimes referred to generically as novocaine. It acts mainly by being a sodium channel blocker. Procaine was first synthesized in 1898[2] and was the first injectable man-made local anesthetic. It was created by the German chemist Alfred Einhorn (1856?1917) who gave the chemical the trade name Novocaine, from the Latin nov- (meaning new) and -caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun (1862?1934). Novocain application before removal of a decayed tooth Procaine is used less frequently today since more effective (and hypoallergenic) alternatives such as lidocaine (Xylocaine) exist. Prior to the discovery of procaine, cocaine was the most commonly used local anesthetic. Like other local anesthetics (with the exception of cocaine), mepivacaine, and prilocaine, procaine is a vasodilator, and is often coadministered with epinephrine for the purpose of vasoconstriction. Vasoconstriction helps to reduce bleeding and prevents the drug from reaching systemic circulation in large amountsand is) also unlike cocaine, procaine does not have the euphoric and addictive qualities that put it at risk for abuse. Procaine, an ester anesthetic, is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-amino benzoic acid (PABA), which is then excreted by the kidneys into the urine. Allergic reactions to procaine are usually not in response to procaine itself, but to PABA. About 1 in 3000 people have an atypical form of pseudocholinesterase, which does not hydrolyze ester anesthetics such as procaine, resulting in a prolonged period of high levels of the anesthetic in the blood and increased toxicity. Procaine is the primary ingredient in the controversial preparation Gerovital H3 by Ana Aslan (Romania), which is claimed by its advocates to remedy many effects of aging. The mainstream medical view is that these claims were seriously studied and discredited in the 1960s. Procaine is occasionally added as an additive in illicit street drugs such as cocaine. (from wiki) [HMDB]
CAS Number59-46-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Diethylaminoethyl p-aminobenzoateChEBI
4-Aminobenzoic acid 2-diethylaminoethyl esterChEBI
beta-(Diethylamino)ethyl 4-aminobenzoateChEBI
beta-(Diethylamino)ethyl p-aminobenzoateChEBI
NovocaineChEBI
p-Aminobenzoic acid 2-diethylaminoethyl esterChEBI
ProcainaChEBI
ProcainumChEBI
Vitamin H3ChEBI
Solution OF novocainKegg
2-Diethylaminoethyl p-aminobenzoic acidGenerator
4-Aminobenzoate 2-diethylaminoethyl esterGenerator
b-(Diethylamino)ethyl 4-aminobenzoateGenerator
b-(Diethylamino)ethyl 4-aminobenzoic acidGenerator
beta-(Diethylamino)ethyl 4-aminobenzoic acidGenerator
Β-(diethylamino)ethyl 4-aminobenzoateGenerator
Β-(diethylamino)ethyl 4-aminobenzoic acidGenerator
b-(Diethylamino)ethyl p-aminobenzoateGenerator
b-(Diethylamino)ethyl p-aminobenzoic acidGenerator
beta-(Diethylamino)ethyl p-aminobenzoic acidGenerator
Β-(diethylamino)ethyl p-aminobenzoateGenerator
Β-(diethylamino)ethyl p-aminobenzoic acidGenerator
p-Aminobenzoate 2-diethylaminoethyl esterGenerator
Procaine HCLHMDB
Chaix et du marais brand OF procaine hydrochlorideHMDB
GeriocaineHMDB
Hewedolor-procainHMDB
Procain jenapharmHMDB
Procain rödlerHMDB
Procain steigerwaldHMDB
Röwo procainHMDB
Abbott brand OF procaine hydrochlorideHMDB
Aventis brand OF procaine hydrochlorideHMDB
Hevert brand OF procaine hydrochlorideHMDB
Hydrochloride, procaineHMDB
Jenapharm brand OF procaine hydrochlorideHMDB
Procain curasanHMDB
Serra pamies brand OF procaine hydrochlorideHMDB
Steigerwald brand OF procaine hydrochlorideHMDB
AnujectHMDB
GerokitHMDB
Lophakomp-procain NHMDB
Procaina serraHMDB
Procaine hydrochlorideHMDB
Pröcaine chlorhydrate lavoisierHMDB
Curasan brand OF procaine hydrochlorideHMDB
Procain-logesHMDB
Braun brand OF procaine hydrochlorideHMDB
Loges brand OF procaine hydrochlorideHMDB
Lomapharm brand OF procaine hydrochlorideHMDB
NovocainHMDB
Pharmakon brand OF procaine hydrochlorideHMDB
Procain braunHMDB
.beta.-(diethylamino)ethyl p-aminobenzoatehmdb
.beta.-(diethylamino)ethyl p-aminobenzoic acidhmdb
.beta.-Diethylaminoethyl 4-aminobenzoatehmdb
.beta.-Diethylaminoethyl 4-aminobenzoic acidhmdb
2-(Diethylamino)ethyl 4-aminobenzoatehmdb
2-(diethylamino)ethyl 4-aminobenzoate (ACD/Name 4.0)hmdb
2-(Diethylamino)ethyl 4-aminobenzoic acidhmdb
2-(Diethylamino)ethyl p-aminobenzoatehmdb
2-(Diethylamino)ethyl p-aminobenzoic acidhmdb
2-(Diethylamino)ethyl-4-aminobenzoatehmdb
2-(Diethylamino)ethyl-4-aminobenzoic acidhmdb
2-Diethylaminoethyl 4-aminobenzoatehmdb
2-Diethylaminoethyl 4-aminobenzoic acidhmdb
2-Diethylaminoethylester kyseliny p-aminobenzoovehmdb
2-Diethylaminoethylester kyseliny p-aminobenzoove [Czech]hmdb
4-Aminobenzoesaeure-beta-diethylaminoethylesterhmdb
4-Aminobenzoic acid 2-(diethylamino) ethyl esterhmdb
4-Aminobenzoic acid diethylaminoethyl esterhmdb
Allocainehmdb
Anticorthmdb
b-(diethylamino)ethyl p-aminobenzoatehmdb
b-(diethylamino)ethyl p-aminobenzoic acidhmdb
b-Diethylaminoethyl 4-aminobenzoatehmdb
b-Diethylaminoethyl 4-aminobenzoic acidhmdb
Benzoic acid, 4-amino-, 2-(diethylamino)ethyl esterhmdb
beta-(diethylamino)ethyl 4-aminobenzoatehmdb
beta-(diethylamino)ethyl 4-aminobenzoic acidhmdb
Beta-(diethylamino)ethyl p-aminobenzoatehmdb
Beta-(diethylamino)ethyl p-aminobenzoic acidhmdb
beta-Diethylaminoethyl 4-aminobenzoatehmdb
beta-Diethylaminoethyl 4-aminobenzoic acidhmdb
Diethylaminoethyl p-aminobenzoatehmdb
Diethylaminoethyl p-aminobenzoic acidhmdb
Duracainehmdb
Factor H3hmdb
Gerovitalhmdb
Gerovital H-3hmdb
Jenacainhmdb
Jenacainehmdb
Neocainehmdb
Nissocainehmdb
Norocainehmdb
p-Aminobenzoic acid, 2-(diethylamino)ethyl esterhmdb
P-aminobenzoyldiethylaminoethanolhmdb
P-aminobenzyoyldiethylaminoethanolhmdb
Procainhmdb
Procaina [inn-spanish]hmdb
Procaine (van)hmdb
Procaine [inn:ban]hmdb
Procaine, basehmdb
Procainum [inn-latin]hmdb
Scurocainehmdb
Spinocainehmdb
Stoff H3hmdb
Predicted Properties
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP2.1ALOGPS
logP1.88ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity70.3 m³·mol⁻¹ChemAxon
Polarizability26.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H20N2O2
IUPAC name2-(diethylamino)ethyl 4-aminobenzoate
InChI IdentifierInChI=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
InChI KeyMFDFERRIHVXMIY-UHFFFAOYSA-N
Isomeric SMILESCCN(CC)CCOC(=O)C1=CC=C(N)C=C1
Average Molecular Weight236.3101
Monoisotopic Molecular Weight236.152477894
Classification
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-9200000000-44eb49be9b2baedfebdd2014-09-20View Spectrum
Predicted GC-MSProcaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-9400000000-a3ea7ca30e23e0b5e656Spectrum
Predicted GC-MSProcaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSProcaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0090000000-7c7d7173da9393c2d0592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0910000000-279febfbe258e2ce28072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0900000000-997e743a0702a7a5b54f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-39c6b968e8d17c932e102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9700000000-157dc94224e66c932ae82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-0900000000-050d794abd6d3a7e685d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01w0-1940000000-d4d5195f000d2d633df72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-3b9d79b65ba8cf449cf72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-0950000000-b3df421e72e07cd2340b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-006x-9500000000-70455df4ef9797d6bd042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-1900000000-5270502b2011d8b676e62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0290000000-cfae604c83e71c8d9b482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-1900000000-1c49e394c0ac65a5b5e72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0h2r-0940000000-fa67a99b73e9f8654ad52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-1900000000-8b6d76215bd17836c1a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0290000000-e14a81a609614ad86d042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0900000000-a05b40f792a408598bf82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00di-4900000000-e07128dfa197867a2d2a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-8cff9a94663a60aec4d42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-1690000000-87e7bf5ac9024bfe7cbb2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-3930000000-18dd034bea68e84f34de2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-983abfba088dd28ad16c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3490000000-1d66ef09f6cac135ebfd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-8980000000-640e85b33add1758148c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-1c06ec2e51e41c54d0632016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC07375
Pubchem Compound ID4914
Pubchem Substance IDNot Available
ChEBI ID8430
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13304
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProcaine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference