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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 17:39:03 UTC
Update Date2023-02-21 17:17:01 UTC
HMDB IDHMDB0004366
Secondary Accession Numbers
  • HMDB04366
Metabolite Identification
Common NameHordenine
DescriptionHordenine, also known as anhalin or cactine, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Hordenine is a very strong basic compound (based on its pKa). Hordenine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Hordenine is found, on average, in the highest concentration within barley. Hordenine has also been detected, but not quantified in, several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds. This could make hordenine a potential biomarker for the consumption of these foods. In a subsequent paper, Camus reported that the intravenous (IV) administration of some hundreds of mg of hordenine sulfate to dogs or rabbits caused an increase in blood pressure and changes in the rhythm and force of contraction of the heart, noting also that the drug was not orally active. Common salts are hordenine hydrochloride, R-NH3+Cl−, m.p. 178 °C, and hordenine sulfate, (R-NH3+)2SO42−, m.p. 211 °C.The "methyl hordenine HCl" which is listed as an ingredient on the labels of some nutritional supplements is in all likelihood simply hordenine hydrochloride, since the "description" of "methyl hordenine HCl" given by virtually all bulk suppliers of this substance corresponds to that for hordenine hydrochloride (or possibly just hordenine). The hordenine content of various malts and malt fractions was extensively studied by Poocharoen himself, who also provided a good coverage of related literature up to 1983.
Structure
Data?1676999821
Synonyms
ValueSource
4-[2-(Dimethylamino)ethyl]phenolChEBI
N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamineChEBI
N,N-Dimethyl-4-hydroxy-beta-phenethylamineChEBI
N,N-DimethyltyramineChEBI
p-(2-Dimethylaminoethyl)phenolChEBI
N,N-Dimethyl-4-hydroxy-b-phenethylamineGenerator
N,N-Dimethyl-4-hydroxy-β-phenethylamineGenerator
Hordenine hydrochlorideHMDB
Hordenine sulfate (2:1)HMDB
Hordenine sulfate (1:1)HMDB
4-(2-Dimethylaminoethyl)phenolHMDB
AnhalinHMDB
AnhalineHMDB
CactineHMDB
EremursineHMDB
HordeninHMDB
HordetinHMDB
N,N-Dimethyl-p-hydroxyphenethylamineHMDB
OrdeninaHMDB
OrdenineHMDB
p-Hydroxy-N,N-dimethylphenethylamineHMDB
p-[2-(Dimethylamino)ethyl]phenolHMDB
PeyocactineHMDB
Chemical FormulaC10H15NO
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
IUPAC Name4-[2-(dimethylamino)ethyl]phenol
Traditional Namehordenine
CAS Registry Number539-15-1
SMILES
CN(C)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
InChI KeyKUBCEEMXQZUPDQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg143.20730932474
[M+H]+MetCCS_train_pos137.80830932474
[M-H]-Not Available143.207http://allccs.zhulab.cn/database/detail?ID=AllCCS00000307
[M+H]+Not Available137.879http://allccs.zhulab.cn/database/detail?ID=AllCCS00000307
Predicted Molecular Properties
PropertyValueSource
Water Solubility29.7 g/LALOGPS
logP1.76ALOGPS
logP1.63ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)10.31ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.34 m³·mol⁻¹ChemAxon
Polarizability19.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.05631661259
DarkChem[M-H]-134.89631661259
DeepCCS[M+H]+138.13230932474
DeepCCS[M-H]-134.31330932474
DeepCCS[M-2H]-172.02130932474
DeepCCS[M+Na]+147.55930932474
AllCCS[M+H]+135.632859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+140.932859911
AllCCS[M-H]-139.232859911
AllCCS[M+Na-2H]-140.532859911
AllCCS[M+HCOO]-141.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HordenineCN(C)CCC1=CC=C(O)C=C12277.5Standard polar33892256
HordenineCN(C)CCC1=CC=C(O)C=C11446.9Standard non polar33892256
HordenineCN(C)CCC1=CC=C(O)C=C11504.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hordenine,1TMS,isomer #1CN(C)CCC1=CC=C(O[Si](C)(C)C)C=C11482.2Semi standard non polar33892256
Hordenine,1TBDMS,isomer #1CN(C)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11730.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9500000000-acdc91b4203b177fc7542017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hordenine GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9310000000-734c4e2c455b973727742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine n/a 11V, negative-QTOFsplash10-0a4i-0900000000-a2d459701f761877da822020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine 10V, Negative-QTOFsplash10-08fr-0900000000-31d50de8a8a2bed634a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine 20V, Negative-QTOFsplash10-0a4i-0900000000-a31932c1e050617567302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine 40V, Negative-QTOFsplash10-014i-0900000000-7837d9fdc06599e5e4772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine QqQ , positive-QTOFsplash10-0uvo-9900000000-130b6ae804451c70f74f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 10V, positive-QTOFsplash10-00xr-0900000000-25885270de2c1836c33b2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 30V, positive-QTOFsplash10-0096-9500000000-8b84d5e79a70fa3d426a2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 50V, positive-QTOFsplash10-00dl-8900000000-31b039648b094d1219b12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 6V, positive-QTOFsplash10-00xr-0900000000-25885270de2c1836c33b2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 3V, positive-QTOFsplash10-014i-0900000000-af85ba014415bf9af0252020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 4V, positive-QTOFsplash10-014i-0900000000-35709636b966d858c1472020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 6V, positive-QTOFsplash10-014i-0900000000-cb918f599a55448f67b12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 8V, positive-QTOFsplash10-014i-0900000000-2c71ef92063a1e597ef92020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 9V, positive-QTOFsplash10-01b9-0900000000-4a5dab8033ea67d49fed2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 11V, positive-QTOFsplash10-00xr-0900000000-ceea75c15d32fbdad6b12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 13V, positive-QTOFsplash10-00di-0900000000-0786df40672ae99b47022020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 14V, positive-QTOFsplash10-00di-0900000000-739407a14a5e392c93bb2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 16V, positive-QTOFsplash10-00di-0900000000-ea6d249aa8c9a27346032020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 18V, positive-QTOFsplash10-00di-0900000000-95ea20554b9c70cfdb042020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 19V, positive-QTOFsplash10-00di-0900000000-840ccb1e804c5f2bd8592020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 21V, positive-QTOFsplash10-00di-1900000000-b5bd97221f7577432dff2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 23V, positive-QTOFsplash10-00di-1900000000-4e1722b74214bbe8fb5d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 24V, positive-QTOFsplash10-00di-2900000000-ace89f936dcba1a150152020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 26V, positive-QTOFsplash10-00di-3900000000-1c1e33c685a2bab4ba2e2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 28V, positive-QTOFsplash10-00dl-4900000000-77c74c5dbd9c018c64f52020-07-21HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012750
KNApSAcK IDC00001417
Chemspider ID61609
KEGG Compound IDC06199
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHordenine
METLIN ID7055
PubChem Compound68313
PDB IDNot Available
ChEBI ID5764
Food Biomarker OntologyNot Available
VMH IDC06199
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLeete, Edward; Kirkwood, Sam; Marion, Leo. The biogenesis of alkaloids. VI. The formation of hordenine and N-methyltyramine, from tyramine in barley. Canadian Journal of Chemistry (1952), 30 749-60.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Singh AK, Granley K, Misrha U, Naeem K, White T, Jiang Y: Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic Sci Int. 1992 Apr;54(1):9-22. [PubMed:1618458 ]

Enzymes

General function:
Involved in protein methyltransferase activity
Specific function:
Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:
PRMT3
Uniprot ID:
O60678
Molecular weight:
59902.7
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
N-Methyltyramine + S-Adenosylmethionine → Hordenine + S-Adenosylhomocysteinedetails