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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:44 UTC
HMDB IDHMDB0014859
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.
Structure
Thumb
Synonyms
ValueSource
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
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 hydrochlorideMeSH
GeriocaineMeSH
Hewedolor-procainMeSH
Procain jenapharmMeSH
Procain rödlerMeSH
Procain steigerwaldMeSH
Röwo procainMeSH
Abbott brand OF procaine hydrochlorideMeSH
Aventis brand OF procaine hydrochlorideMeSH
Hevert brand OF procaine hydrochlorideMeSH
Hydrochloride, procaineMeSH
Jenapharm brand OF procaine hydrochlorideMeSH
Procain curasanMeSH
Serra pamies brand OF procaine hydrochlorideMeSH
Steigerwald brand OF procaine hydrochlorideMeSH
AnujectMeSH
GerokitMeSH
Lophakomp-procain NMeSH
Procaina serraMeSH
Procaine hydrochlorideMeSH
Pröcaine chlorhydrate lavoisierMeSH
Curasan brand OF procaine hydrochlorideMeSH
Procain-logesMeSH
Braun brand OF procaine hydrochlorideMeSH
Loges brand OF procaine hydrochlorideMeSH
Lomapharm brand OF procaine hydrochlorideMeSH
NovocainMeSH
Pharmakon brand OF procaine hydrochlorideMeSH
Procain braunMeSH
Chemical FormulaC13H20N2O2
Average Molecular Weight236.3101
Monoisotopic Molecular Weight236.152477894
IUPAC Name2-(diethylamino)ethyl 4-aminobenzoate
Traditional Nameprocaine
CAS Registry Number59-46-1
SMILES
CCN(CC)CCOC(=O)C1=CC=C(N)C=C1
InChI Identifier
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
InChI KeyMFDFERRIHVXMIY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

  Parenteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Psychiatric disorders:

    General disorders and administration site conditions:

    Nervous system disorders:

  Observation:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.81 g/LNot Available
LogP1.8Not Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0090000000-7c7d7173da9393c2d059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0910000000-279febfbe258e2ce2807View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0900000000-997e743a0702a7a5b54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-39c6b968e8d17c932e10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9700000000-157dc94224e66c932ae8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-0900000000-050d794abd6d3a7e685dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01w0-1940000000-d4d5195f000d2d633df7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-1690000000-87e7bf5ac9024bfe7cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-3930000000-18dd034bea68e84f34deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-983abfba088dd28ad16cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3490000000-1d66ef09f6cac135ebfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-8980000000-640e85b33add1758148cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-1c06ec2e51e41c54d063View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-9200000000-44eb49be9b2baedfebddView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Procaine PathwayPw000408Pw000408 greyscalePw000408 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00721 details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Not AvailableNot AvailableNormal details
    UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00721 details
    Abnormal Concentrations
    Not Available
    Predicted Concentrations
    BiofluidValueOriginal ageOriginal sexOriginal conditionComments
    Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDDB00721
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDNot Available
    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
    References
    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 ]

    Enzymes

    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:
    BCHE
    Uniprot ID:
    P06276
    Molecular weight:
    68417.575
    References
    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:
    SLC6A3
    Uniprot ID:
    Q01959
    Molecular weight:
    68494.255
    References
    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:
    HTR3A
    Uniprot ID:
    P46098
    Molecular weight:
    55279.8
    References
    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:
    GRIN3A
    Uniprot ID:
    Q8TCU5
    Molecular weight:
    125464.1
    References
    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:
    SCN10A
    Uniprot ID:
    Q9Y5Y9
    Molecular weight:
    220623.6
    References
    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:
    CHRNA2
    Uniprot ID:
    Q15822
    Molecular weight:
    59764.8
    References
    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 ]