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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-16 10:59:41 UTC

Update Date

2023-02-21 17:17:06 UTC

HMDB ID

HMDB0004992

Secondary Accession Numbers

HMDB04992

Metabolite Identification

Common Name

Benzocaine

Description

Benzocaine is a surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1086                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748   2.549   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   2.549   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414  -4.381   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414   0.239   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -0.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -0.531   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -2.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -2.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -2.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   4.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   4.859   0.000  0.00  0.00           C+0
CONECT    1   10   11                                                       
CONECT    2   10                                                            
CONECT    3    7                                                            
CONECT    4    5    6   10                                                  
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3    8    9                                                  
CONECT    8    5    7                                                       
CONECT    9    6    7                                                       
CONECT   10    1    2    4                                                  
CONECT   11    1   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Aminobenzoic acid ethyl ester	ChEBI
Amben ethyl ester	ChEBI
Benzocaina	ChEBI
Benzocainum	ChEBI
Ethyl aminobenzoate	ChEBI
Ethyl p-aminobenzoate	ChEBI
Ethyl p-aminophenylcarboxylate	ChEBI
p-(Ethoxycarbonyl)aniline	ChEBI
p-Carbethoxyaniline	ChEBI
p-Ethoxycarboxylic aniline	ChEBI
Parathesin	Kegg
4-Aminobenzoate ethyl ester	Generator
Ethyl aminobenzoic acid	Generator
Ethyl p-aminobenzoic acid	Generator
Ethyl p-aminophenylcarboxylic acid	Generator
(P-(Ethoxycarbonyl)phenylamine	HMDB
4-(Ethoxycarbonyl)aniline	HMDB
4-(Ethoxycarbonyl)phenylamine	HMDB
4-Aminobenzoate	HMDB
4-Aminobenzoic acid	HMDB
4-Carbethoxyaniline	HMDB
Aethoform	HMDB
Americaine	HMDB, MeSH
Anaesthan-syngala	HMDB
Anaesthesin	HMDB, MeSH
Anaesthin	HMDB
Anestezin	HMDB
Anesthesin	HMDB, MeSH
Anesthesine	HMDB
Anesthone	HMDB
Baby anbesol	HMDB
Benzoak	HMDB
Dermoplast	HMDB
Diet ayds	HMDB
Ethoform	HMDB, MeSH
Ethyl 4-aminobenzoate	HMDB
Ethyl 4-aminobenzoic acid	HMDB
Ethyl P-aminobenzenecarboxylate	HMDB
Ethylester kyseliny P-aminobenzoove	HMDB
Hurricaine	HMDB
Identhesin	HMDB
Keloform	HMDB
Norcain	HMDB
Norcaine	HMDB
Ora-jel	HMDB
Orabase-b	HMDB
Orthesin	HMDB
P-Aminobenzoate	HMDB
P-Aminobenzoic acid	HMDB
P-Aminobenzoic acid ethyl ester	HMDB
Parathesine	HMDB
Slim mint gum	HMDB
Solarcaine	HMDB
Solu H	HMDB
Topcaine	HMDB
Benzocaine acetate	MeSH, HMDB
Formate, benzocaine	MeSH, HMDB
Acetate, benzocaine	MeSH, HMDB
Benzocaine formate	MeSH, HMDB
Hydrobromide, benzocaine	MeSH, HMDB
Methanesulfonate, benzocaine	MeSH, HMDB
Bensokain	MeSH, HMDB
Benzocaine hydrochloride	MeSH, HMDB
Benzocaine hydrobromide	MeSH, HMDB
Benzocaine methanesulfonate	MeSH, HMDB
Hydrochloride, benzocaine	MeSH, HMDB

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

ethyl 4-aminobenzoate

Traditional Name

benzocaine

CAS Registry Number

94-09-7

SMILES

CCOC(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3

InChI Key

BLFLLBZGZJTVJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:116735 )
benzoate ester (CHEBI:116735 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	92 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	23320 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.86	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	148.2	30932474
[M+H]+	Not Available	145.903	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000755

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.85 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	2.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.53 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.869	31661259
DarkChem	[M-H]-	135.045	31661259
DeepCCS	[M+H]+	139.074	30932474
DeepCCS	[M-H]-	135.475	30932474
DeepCCS	[M-2H]-	172.811	30932474
DeepCCS	[M+Na]+	148.35	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	140.1	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	137.9	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.63 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8549 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1505.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	366.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	365.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	394.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	956.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	308.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1069.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	93.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzocaine	CCOC(=O)C1=CC=C(N)C=C1	2483.7	Standard polar	33892256
Benzocaine	CCOC(=O)C1=CC=C(N)C=C1	1490.8	Standard non polar	33892256
Benzocaine	CCOC(=O)C1=CC=C(N)C=C1	1597.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzocaine,1TMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	1799.7	Semi standard non polar	33892256
Benzocaine,1TMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	1797.8	Standard non polar	33892256
Benzocaine,1TMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2017.5	Standard polar	33892256
Benzocaine,2TMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1786.3	Semi standard non polar	33892256
Benzocaine,2TMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1868.0	Standard non polar	33892256
Benzocaine,2TMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1943.2	Standard polar	33892256
Benzocaine,1TBDMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2015.5	Semi standard non polar	33892256
Benzocaine,1TBDMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	1995.9	Standard non polar	33892256
Benzocaine,1TBDMS,isomer #1	CCOC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2148.6	Standard polar	33892256
Benzocaine,2TBDMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2279.3	Semi standard non polar	33892256
Benzocaine,2TBDMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2248.0	Standard non polar	33892256
Benzocaine,2TBDMS,isomer #1	CCOC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2157.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzocaine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine EI-B (Non-derivatized)	splash10-00di-4900000000-9341302295e361a20bfd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine EI-B (Non-derivatized)	splash10-0109-9400000000-8e31c925b871e0f0299e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine EI-B (Non-derivatized)	splash10-0109-9400000000-c755b4e5336a2867357e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine EI-B (Non-derivatized)	splash10-01b9-1900000000-a811093acfd0672fece6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine CI-B (Non-derivatized)	splash10-014i-0900000000-49302e8e4fd5158a36da	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine EI-B (Non-derivatized)	splash10-00di-5900000000-dcd2847110af7c87bf18	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzocaine GC-EI-TOF (Non-derivatized)	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-8d1e571ebb0276875b64	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzocaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00xr-6900000000-0594451f3b181ab3c883	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00kr-0900000000-b54aebb77e7a69ada07c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-5900000000-ce90658bd0fc66df820d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-03xu-9100000000-5179b7804d2c59e71aa4	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine EI-B (HITACHI RMU-7M) , Positive-QTOF	splash10-00di-4900000000-9341302295e361a20bfd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine EI-B (HITACHI RMU-7) , Positive-QTOF	splash10-0109-9400000000-8e31c925b871e0f0299e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine EI-B (HITACHI RMU-6D) , Positive-QTOF	splash10-0109-9400000000-c755b4e5336a2867357e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine EI-B (HITACHI M-60) , Positive-QTOF	splash10-01b9-1900000000-57d39b512bc5bdbb4987	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine CI-B (HITACHI M-60) , Positive-QTOF	splash10-014i-0900000000-49302e8e4fd5158a36da	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine EI-B (JEOL JMS-DX-300) , Positive-QTOF	splash10-00di-5900000000-dcd2847110af7c87bf18	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-014i-0900000000-a0f10abbe67842c2c958	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00du-5900000000-43a89461a4d9cc5d1409	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00dl-9600000000-049e2653cbbf24aaf010	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-002f-9100000000-6fbc7720b326773643af	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-00ou-9000000000-d7f7622c3a270c5ffcbb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-qTof , Positive-QTOF	splash10-000i-5900100000-72ac4bcb64db0d25261e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ , positive-QTOF	splash10-014i-0900000000-e061a0f4172b47a8bd22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ , positive-QTOF	splash10-00du-5900000000-54757e57c91d3eaa1976	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ , positive-QTOF	splash10-00dl-9600000000-049e2653cbbf24aaf010	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzocaine LC-ESI-QQ , positive-QTOF	splash10-002f-9100000000-e16fc2db7a632fc6f4da	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 10V, Positive-QTOF	splash10-014j-0900000000-4479c2a548f4aa1aa697	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 20V, Positive-QTOF	splash10-00xr-0900000000-45723c7ad554a9d56bd1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 40V, Positive-QTOF	splash10-0006-9300000000-fab7bee6cbcfbc918d9c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 10V, Negative-QTOF	splash10-03di-1900000000-477a27b8617485132384	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 20V, Negative-QTOF	splash10-03xr-3900000000-df3eaaf30a4e906fb038	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzocaine 40V, Negative-QTOF	splash10-00kf-9400000000-e9f4c1de93ac2ce072b4	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Benzocaine Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01086

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023574

KNApSAcK ID

Not Available

Chemspider ID

13854242

KEGG Compound ID

C07527

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzocaine

METLIN ID

3934

PubChem Compound

2337

PDB ID

Not Available

ChEBI ID

116735

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836611

References

Synthesis Reference

Salts from naphtholmonosulphonic acids and p-aminobensoic acid ethyl ether. (1904), DE 181324 19040213 CAN 1:9748 AN 1907:9748

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Bong CL, Hilliard J, Seefelder C: Severe methemoglobinemia from topical benzocaine 7.5% (baby orajel) use for teething pain in a toddler. Clin Pediatr (Phila). 2009 Mar;48(2):209-11. doi: 10.1177/0009922808324491. Epub 2008 Oct 3. [PubMed:18836057 ]
FENTON PF, COWGILL GR, STONE MA, JUSTICE DH: The nutrition of the mouse. VIII. Studies on pantothenic acid, biotin, inositol and paminobenzoic acid. J Nutr. 1950 Oct;42(2):257-69. [PubMed:14795275 ]

Enzymes

Enzyme Details

1. Sodium channel protein type 10 subunit alpha

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

Showing metabocard for Benzocaine (HMDB0004992)

MOL for HMDB0004992 (Benzocaine)

3D MOL for HMDB0004992 (Benzocaine)

3D SDF for HMDB0004992 (Benzocaine)

3D-SDF for HMDB0004992 (Benzocaine)

PDB for HMDB0004992 (Benzocaine)

3D PDB for HMDB0004992 (Benzocaine)

SMILES for HMDB0004992 (Benzocaine)

INCHI for HMDB0004992 (Benzocaine)

Structure for HMDB0004992 (Benzocaine)

3D Structure for HMDB0004992 (Benzocaine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes