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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:38:40 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033871
Secondary Accession Numbers
  • HMDB33871
Metabolite Identification
Common NameBenzylamine
DescriptionBenzylamine, also known as a-aminotoluene or moringine, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. Benzylamine is found, on average, in the highest concentration within a few different foods, such as corns, white cabbages, and cabbages and in a lower concentration in wild carrots, carrots, and apples. Benzylamine has also been detected, but not quantified, in several different foods, such as common chokecherries, black cabbages, macadamia nut (m. tetraphylla), ginsengs, and lettuces. This could make benzylamine a potential biomarker for the consumption of these foods.
Structure
Data?1563862473
Synonyms
ValueSource
(Aminomethyl)benzeneChEBI
(Phenylmethyl)amineChEBI
alpha-AminotolueneChEBI
BenzenemethanamineChEBI
MonobenzylamineChEBI
MoringineChEBI
N-BenzylamineChEBI
Omega-aminotolueneChEBI
a-AminotolueneGenerator
Α-aminotolueneGenerator
Benzylamine hydrobromideMeSH
Benzylamine hydrochlorideMeSH
Benzylamine monosulfateMeSH
.omega.-aminotolueneHMDB
1-PhenylmethanamineHMDB
1UtjHMDB
1UtnHMDB
2BzaHMDB
ABNHMDB
AminotolueneHMDB
Benzenemethanamine, 9ciHMDB
laquo omegaraquo -AminotolueneHMDB
PhenylmethanamineHMDB
Quadrapure(TM) benzylamineHMDB
Quadrapure(TM) bzaHMDB
Sumine 2005HMDB
Sumine 2006HMDB
Toluene,alpha-aminoHMDB
Chemical FormulaC7H9N
Average Molecular Weight107.1531
Monoisotopic Molecular Weight107.073499293
IUPAC Namephenylmethanamine
Traditional Namebenzylamine
CAS Registry Number100-46-9
SMILES
NCC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
InChI KeyWGQKYBSKWIADBV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point10 °CNot Available
Boiling Point185.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP1.09Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.71 g/LALOGPS
logP0.9ALOGPS
logP1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)9.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.53 m³·mol⁻¹ChemAxon
Polarizability12.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.80231661259
DarkChem[M-H]-117.76131661259
DeepCCS[M+H]+122.03530932474
DeepCCS[M-H]-119.41630932474
DeepCCS[M-2H]-155.73330932474
DeepCCS[M+Na]+130.39430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzylamineNCC1=CC=CC=C11378.1Standard polar33892256
BenzylamineNCC1=CC=CC=C1971.1Standard non polar33892256
BenzylamineNCC1=CC=CC=C11015.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzylamine,1TMS,isomer #1C[Si](C)(C)NCC1=CC=CC=C11231.7Semi standard non polar33892256
Benzylamine,1TMS,isomer #1C[Si](C)(C)NCC1=CC=CC=C11182.7Standard non polar33892256
Benzylamine,2TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)[Si](C)(C)C1425.5Semi standard non polar33892256
Benzylamine,2TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)[Si](C)(C)C1400.6Standard non polar33892256
Benzylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=CC=CC=C11457.1Semi standard non polar33892256
Benzylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=CC=CC=C11409.5Standard non polar33892256
Benzylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C1832.7Semi standard non polar33892256
Benzylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C1802.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzylamine GC-MS (2 TMS)splash10-01p9-4920000000-0f4ada396b9bee5414852014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylamine EI-B (Non-derivatized)splash10-0a6r-9600000000-76805d0c1bcba470e1e92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylamine EI-B (Non-derivatized)splash10-0a6r-9500000000-3b232f493a2c14360f5f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylamine EI-B (Non-derivatized)splash10-0a6r-9700000000-7e253eff483b8a31ec7a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylamine GC-MS (Non-derivatized)splash10-01p9-4920000000-0f4ada396b9bee5414852017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylamine GC-EI-TOF (Non-derivatized)splash10-000i-3920000000-24949e7f9e479e44f96a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9400000000-012edeef3ad21b1f83fd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-7ef28c10b30a125e9a042015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-79ff95be504a5efad2642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-79ff95be504a5efad2642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-79ff95be504a5efad2642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-864a48552fea562fc3702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-79ff95be504a5efad2642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-8427480b81d41b80571e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-10b0a2c3d32b9a216fb02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-eae6015976352ec30df32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-f5b6e01ed535982c3a2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-546d86dcbfb4752d07392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-f81d8a7234ccf1e8d6b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-f49cbaea9ee4d92d9d2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-0006-9000000000-1180a5ab497a1bedf7532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine ESI-ITFT , positive-QTOFsplash10-00kf-9000000000-df34f470ef53726c9f4c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine LC-ESI-QFT , positive-QTOFsplash10-0a4i-0900000000-de01e2fbc1afc209a4982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine 45V, Positive-QTOFsplash10-0006-9000000000-79ff95be504a5efad2642021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine 120V, Positive-QTOFsplash10-0006-9000000000-5dca33a19b0cd29583ff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine 105V, Positive-QTOFsplash10-0006-9000000000-a252dadec22c2a6b26b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylamine 30V, Positive-QTOFsplash10-0006-9000000000-8427480b81d41b80571e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 10V, Positive-QTOFsplash10-0a4i-0900000000-2ea49c7261b19840449d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 20V, Positive-QTOFsplash10-0a4i-1900000000-4c1b78093f6f02248c712015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 40V, Positive-QTOFsplash10-1029-9100000000-ae7d6de0223ba67982ac2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 10V, Negative-QTOFsplash10-0a4i-1900000000-aabc088d9596196c825a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 20V, Negative-QTOFsplash10-0a4i-3900000000-9f49843e6a51d164a1152015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylamine 40V, Negative-QTOFsplash10-004i-9100000000-bc7bd1bfabbb6f8aff5b2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified<1 nmol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02464
Phenol Explorer Compound IDNot Available
FooDB IDFDB012059
KNApSAcK IDC00043309
Chemspider ID7223
KEGG Compound IDC15562
BioCyc IDBENZYLAMINE
BiGG IDNot Available
Wikipedia LinkBenzylamine
METLIN IDNot Available
PubChem Compound7504
PDB IDABN
ChEBI ID40538
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1222661
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iffiu-Soltesz' Z, Prevot D, Gres S, Bour S, Szoko E, Knauf C, Burcelin R, Fernandez-Quintela A, Lomba A, Milagro FI, Carpene C: Influence of acute and chronic administration of benzylamine on glucose tolerance in diabetic and obese mice fed on very high-fat diet. J Physiol Biochem. 2007 Dec;63(4):305-15. [PubMed:18457006 ]
  2. Ramirez F, Shiuan D, Tu SI, Marecek JF: Differential effects on energy transduction processes by fluorescamine derivatives in rat liver mitochondria. Biochemistry. 1980 Apr 29;19(9):1928-33. [PubMed:6445750 ]
  3. Nussbaumer P, Dorfstatter G, Grassberger MA, Leitner I, Meingassner JG, Thirring K, Stutz A: Synthesis and structure-activity relationships of phenyl-substituted benzylamine antimycotics: a novel benzylbenzylamine antifungal agent for systemic treatment. J Med Chem. 1993 Jul 23;36(15):2115-20. [PubMed:8340915 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in serine-type endopeptidase activity
Specific function:
Has activity against the synthetic substrates Boc-Phe- Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val- Pro-Arg-Mec. The single-chain form is more active than the two- chain form against all of these substrates
Gene Name:
PRSS1
Uniprot ID:
P07477
Molecular weight:
26557.9
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in serine-type endopeptidase activity
Specific function:
Preferential cleavage:Arg-|-Xaa, Lys-|-Xaa
Gene Name:
PRSS2
Uniprot ID:
P07478
Molecular weight:
26487.6
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]