You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusDetected and Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:29 UTC
Secondary Accession Numbers
  • HMDB14859
Metabolite Identification
Common NameProcaine
DescriptionProcaine is only found in individuals that have used or taken this drug. It is 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). [PubChem]Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.
2-Diethylaminoethyl p-aminobenzoateChEBI
4-Aminobenzoic acid 2-diethylaminoethyl esterChEBI
beta-(Diethylamino)ethyl 4-aminobenzoateChEBI
beta-(Diethylamino)ethyl p-aminobenzoateChEBI
p-Aminobenzoic acid 2-diethylaminoethyl esterChEBI
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
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
Lophakomp-procain NHMDB
Procaina serraHMDB
Procaine hydrochlorideHMDB
Pröcaine chlorhydrate lavoisierHMDB
Curasan brand OF procaine hydrochlorideHMDB
Braun brand OF procaine hydrochlorideHMDB
Loges brand OF procaine hydrochlorideHMDB
Lomapharm brand OF procaine hydrochlorideHMDB
Pharmakon brand OF procaine hydrochlorideHMDB
Procain braunHMDB
Chemical FormulaC13H20N2O2
Average Molecular Weight236.3101
Monoisotopic Molecular Weight236.152477894
IUPAC Name2-(diethylamino)ethyl 4-aminobenzoate
Traditional Nameprocaine
CAS Registry Number59-46-1
InChI Identifier
Chemical Taxonomy
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
  • 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
Physiological effect

Health effect:


Route of exposure:

Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point61 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.81 g/LNot Available
LogP1.8Not Available
Predicted Properties
Water Solubility6.81 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-9400000000-a3ea7ca30e23e0b5e656Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0090000000-7c7d7173da9393c2d059Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0910000000-279febfbe258e2ce2807Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0900000000-997e743a0702a7a5b54fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-39c6b968e8d17c932e10Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9700000000-157dc94224e66c932ae8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-0900000000-050d794abd6d3a7e685dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01w0-1940000000-d4d5195f000d2d633df7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-1690000000-87e7bf5ac9024bfe7cbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-3930000000-18dd034bea68e84f34deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-983abfba088dd28ad16cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3490000000-1d66ef09f6cac135ebfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-8980000000-640e85b33add1758148cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-1c06ec2e51e41c54d063Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-9200000000-44eb49be9b2baedfebddSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00721 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
      Not Available
UrineDetected and Quantified0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00721 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00721
Phenol Explorer Compound IDNot Available
FooDB IDFDB029371
KNApSAcK IDNot Available
Chemspider ID4745
KEGG Compound IDC07375
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcaine
METLIN IDNot Available
PubChem Compound4914
PDB IDNot Available
ChEBI ID8430
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. J Pharmacol Exp Ther. 2001 Dec;299(3):1038-48. [PubMed:11714893 ]


General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Perez-Guillermo F, Delgado EM, Vidal CJ: Inhibition of human serum and rabbit muscle cholinesterase by local anesthetics. Biochem Pharmacol. 1987 Nov 1;36(21):3593-6. [PubMed:3675616 ]
  2. Dorokhov KE, Grigorian GL: [Binding of reversible spin-labeled inhibitors with an butyrylcholinesterase active center]. Biofizika. 1986 Sep-Oct;31(5):746-51. [PubMed:3022829 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T: Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics. Naunyn Schmiedebergs Arch Pharmacol. 2000 Feb;361(2):214-20. [PubMed:10685879 ]
  2. Wilcox KM, Kimmel HL, Lindsey KP, Votaw JR, Goodman MM, Howell LL: In vivo comparison of the reinforcing and dopamine transporter effects of local anesthetics in rhesus monkeys. Synapse. 2005 Dec 15;58(4):220-8. [PubMed:16206183 ]
  3. Kiyatkin EA, Brown PL: The role of peripheral and central sodium channels in mediating brain temperature fluctuations induced by intravenous cocaine. Brain Res. 2006 Oct 30;1117(1):38-53. Epub 2006 Sep 7. [PubMed:16956595 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:
Uniprot ID:
Molecular weight:
  1. Fan P, Weight FF: Procaine impairs the function of 5-HT3 receptor-ion channel complex in rat sensory ganglion neurons. Neuropharmacology. 1994 Dec;33(12):1573-9. [PubMed:7539114 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:
Uniprot ID:
Molecular weight:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Hahnenkamp K, Durieux ME, Hahnenkamp A, Schauerte SK, Hoenemann CW, Vegh V, Theilmeier G, Hollmann MW: Local anaesthetics inhibit signalling of human NMDA receptors recombinantly expressed in Xenopus laevis oocytes: role of protein kinase C. Br J Anaesth. 2006 Jan;96(1):77-87. Epub 2005 Nov 18. [PubMed:16299047 ]
  4. Nishizawa N, Shirasaki T, Nakao S, Matsuda H, Shingu K: The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons. Anesth Analg. 2002 Feb;94(2):325-30, table of contents. [PubMed:11812692 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
Uniprot ID:
Molecular weight:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Brau ME, Vogel W, Hempelmann G: Fundamental properties of local anesthetics: half-maximal blocking concentrations for tonic block of Na+ and K+ channels in peripheral nerve. Anesth Analg. 1998 Oct;87(4):885-9. [PubMed:9768788 ]
  4. Katalymov LL: [The effect of inhibitors of sodium permeability (novocaine and tetrodotoxin) on the trace depolarization of myelinated nerve fibers]. Fiziol Zh Im I M Sechenova. 1995 Sep;81(9):127-33. [PubMed:8581044 ]
  5. Creveling CR, Bell ME, Burke TR Jr, Chang E, Lewandowski-Lovenberg GA, Kim CH, Rice KC, Daly JW: Procaine isothiocyanate: an irreversible inhibitor of the specific binding of [3H]batrachotoxinin-A benzoate to sodium channels. Neurochem Res. 1990 Apr;15(4):441-8. [PubMed:2167458 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
Uniprot ID:
Molecular weight:
  1. Wang H, Zhang Y, Li ST: The effect of local anesthetics on the inhibition of adult muscle-type nicotinic acetylcholine receptors by nondepolarizing muscle relaxants. Eur J Pharmacol. 2010 Mar 25;630(1-3):29-33. doi: 10.1016/j.ejphar.2009.12.028. Epub 2010 Jan 4. [PubMed:20045405 ]