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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-09 16:06:27 UTC
NP-MRD IDNP0000398
Secondary Accession NumbersNone
Natural Product Identification
Common NameTyramine
DescriptionTyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. Tyramine is a biomarker for the consumption of cheese
Structure
Thumb
Synonyms
ValueSource
2-(p-Hydroxyphenyl)ethylamineChEBI
4-Hydroxy-beta-phenylethylamineChEBI
4-HydroxyphenethylamineChEBI
4-HydroxyphenylethylamineChEBI
beta-(4-Hydroxyphenyl)ethylamineChEBI
p-(2-Aminoethyl)phenolChEBI
p-HydroxyphenethylamineChEBI
p-HydroxyphenylethylamineChEBI
p-TyramineChEBI
TyraminChEBI
4-Hydroxy-b-phenylethylamineGenerator
4-Hydroxy-β-phenylethylamineGenerator
b-(4-Hydroxyphenyl)ethylamineGenerator
Β-(4-hydroxyphenyl)ethylamineGenerator
2-(4'-Hydroxyphenyl)ethylamineHMDB
2-(4-Hydroxyphenyl)ethylamineHMDB
4-(2-Aminoethyl)-phenolHMDB
4-(2-Aminoethyl)-phenol(thyramin)HMDB
4-(2-Aminoethyl)phenolHMDB
4-Hydroxy-benzeneethanamineHMDB
a-(4-Hydroxyphenyl)-b-aminoethaneHMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethaneHMDB
p-(2-Aminoethyl)-phenolHMDB
p-beta-AminoethylphenolHMDB
p-Hydroxy-b-phenethylamineHMDB
p-Hydroxy-b-phenylethylamineHMDB
p-Hydroxy-beta-phenethylamineHMDB
p-Hydroxy-beta-phenylethylamineHMDB
SystogeneHMDB
Tenosin-wirkstoffHMDB
TocosineHMDB
Tyramine baseHMDB
TyrosamineHMDB
UteramineHMDB
Para-tyramineHMDB
4 HydroxyphenethylamineHMDB
2-(4-Hydroxyphenyl)ethanamineHMDB
2-(4’-hydroxyphenyl)ethylamineHMDB
p-Hydroxy-β-phenylethylamineHMDB
p-Β-aminoethylphenolHMDB
Α-(4-hydroxyphenyl)-β-aminoethaneHMDB
Chemical FormulaC8H11NO
Average Mass137.1790 Da
Monoisotopic Mass137.08406 Da
IUPAC Name4-(2-aminoethyl)phenol
Traditional Nametyramine
CAS Registry Number51-67-2
SMILES
NCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
InChI KeyDZGWFCGJZKJUFP-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Acacia angustissimaKNApSAcK Database
Acacia greggiiKNApSAcK Database
Acacia rigidula Benth.KNApSAcK Database
Acacia roemerianaKNApSAcK Database
Actaea racemosaKNApSAcK Database
Actinidia chinensis
Adenocarpus hispanicusKNApSAcK Database
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Allium victorialisKNApSAcK Database
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anas platyrhynchos
Anatidae
Anethum graveolens
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefolium
Antirrhinum majusKNApSAcK Database
Apiaceae-
Apium graveolens
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaea
Arctium lappa
Argemone mexicanaKNApSAcK Database
Aristolochia giganteaKNApSAcK Database
Armoracia rusticana
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambola
Basella alba
Benincasa hispida
Berberis amurensisKNApSAcK Database
Berberis aquifoliumKNApSAcK Database
Berberis aristataKNApSAcK Database
Berberis thunbergiiKNApSAcK Database
Berberis vulgarisKNApSAcK Database
Berberis wilsoniaeKNApSAcK Database
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Bison bison
Borago officinalis
Bos taurus
Bos taurus X Bison bison
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica olereaceaKNApSAcK Database
Brassica rapaFooDB
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capra aegagrus hircus
Capsella bursa-pastorisKNApSAcK Database
Capsicum annuum
Capsicum annuum L.
Capsicum annuum var. annuumFooDB
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Caulophyllum thalicroidesKNApSAcK Database
Ceratonia siliqua
Cervidae
Cervus canadensis
Chamaemelum nobile
Chamerion angustifolium
Chelidonium majusKNApSAcK Database
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Cissampelos pareiraKNApSAcK Database
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus aurantium L. var. amaraKNApSAcK Database
Citrus bergamiaKNApSAcK Database
Citrus latifolia
Citrus limonKNApSAcK Database
Citrus maxima
Citrus medicaKNApSAcK Database
Citrus paradisi
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clematis parvilobaKNApSAcK Database
Cocculus diversifoliusKNApSAcK Database
Cocculus japonicusKNApSAcK Database
Cocos nucifera
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Columba
Columbidae
Coptis japonicaKNApSAcK Database
Corchorus olitorius
Coriandrum sativum L.
Corydalis cavaKNApSAcK Database
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cyclea barbataKNApSAcK Database
Cyclea peltataKNApSAcK Database
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Cytisus scopariusKNApSAcK Database
Datura innoxiaKNApSAcK Database
Datura inoxiaPlant
Daucus carota
Daucus carota ssp. sativus
Delphinium pentagynumKNApSAcK Database
Dendrolobium triangulareKNApSAcK Database
Desmodium elegansKNApSAcK Database
Desmodium triflorumKNApSAcK Database
Dicentra spectabilisKNApSAcK Database
Dilphinium caeruleum-
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Dromaius novaehollandiae
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Equus caballus
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Erythrina crista-galliKNApSAcK Database
Eschscholzia californicaKNApSAcK Database
Espostoa huanucensisKNApSAcK Database
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassaFooDB
Fumaria officinalisKNApSAcK Database
Gallus gallus
Garcinia mangostana
Gaylussacia baccata
Ginkgo biloba
Glaucium flavumKNApSAcK Database
Gleditsia triacanthosKNApSAcK Database
Glycine maxKNApSAcK Database
Gnetum montanumKNApSAcK Database
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgareKNApSAcK Database
Hydrastis canadensisKNApSAcK Database
Hypecoum lactiflorumKNApSAcK Database
Hyssopus officinalis L.
Illicium verum
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lagopus muta
Lamium barbatumKNApSAcK Database
Lathyrus sativus
Laurus nobilis L.
Lens culinaris
Lentinus edodes
Lepidium sativum
Leporidae
Lepus timidus
Levisticum officinale
Lindera angustifoliaKNApSAcK Database
Linum usitatissimum
Liparia parvaKNApSAcK Database
Liparia splendensKNApSAcK Database
Litchi chinensis
Lobivia bachenbergii-
Lobivia binghamiana-
Lobivia pentlandii-
Lolium multiflorumKNApSAcK Database
Lophophora williamsiiKNApSAcK Database
Luffa aegyptiaca
Lupinus
Lupinus albus
Lyallia kerguelensisKNApSAcK Database
Macadamia
Macadamia tetraphylla
Macleaya cordataKNApSAcK Database
Magnolia obovataKNApSAcK Database
Magnolia officinalisKNApSAcK Database
Mahonia aquifoliumKNApSAcK Database
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Meconopsis cambricaKNApSAcK Database
Medicago sativa
Melanitta fusca
Meleagris gallopavo
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Mohonia bealei-
Momordica charantia
Monodora junodiiKNApSAcK Database
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminataKNApSAcK Database
Musa sapientumKNApSAcK Database
Musa x paradisiacaPlant
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Numida meleagris
Nuphar lutea
Ocimum basilicum
Odocoileus
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryctolagus
Oryza rufipogon
Oryza sativa
Ovis aries
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceumKNApSAcK Database
Papaver bracteatumKNApSAcK Database
Papaver rhoeasKNApSAcK Database
Papaver somniferumKNApSAcK Database
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Pereskia aculeataKNApSAcK Database
Perideridia oregana
Persea americanaKNApSAcK Database
Petasites japonicus
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgarisKNApSAcK Database
Phasianidae
Phasianus colchicus
Phellodendron chinensisKNApSAcK Database
Phoenix dactylifera
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
Pinus
Pinus edulis
Piper nigrumKNApSAcK Database
Piper nigrum L.Plant
Pistacia vera
Pisum sativumKNApSAcK Database
Plantago majorKNApSAcK Database
Pleurotus ostreatus
Polygonum alpinum
Portulaca grandifloraKNApSAcK Database
Portulaca oleracea
Pouteria sapota
Prosopis albaKNApSAcK Database
Prosopis glandulosaKNApSAcK Database
Prosopis nigraKNApSAcK Database
Prunus armeniaca
Prunus avium
Prunus avium L.
Prunus cerasus
Prunus domesticaFooDB
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Pseudolobivia kermesina-
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
Pyrus communis
Pyrus pyrifolia
Quercus
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Rhodiola roseaKNApSAcK Database
Rhodiola sachalinensisKNApSAcK Database
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Romneya coulteriKNApSAcK Database
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Secale cereale
Sechium edule
Senna alataKNApSAcK Database
Sesamum indicum
Sesbania bispinosa
Silybum marianumKNApSAcK Database
Sinapis alba
Sisymbrium
Solanum esculentumKNApSAcK Database
Solanum lycopersicumFooDB
Solanum lycopersicum L.KNApSAcK Database
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melanogenaKNApSAcK Database
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumKNApSAcK Database
Sorbus aucuparia
Sorghum bicolor
Spinacia oleraceaKNApSAcK Database
Stapelia hirsutaKNApSAcK Database
Stephania hernandifoliaKNApSAcK Database
Stephania tetrandraKNApSAcK Database
Struthio camelus
Sus scrofa
Sus scrofa domestica
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tephrosia noctifloraKNApSAcK Database
Tetragonia tetragonioides
Thalictrum flavumKNApSAcK Database
Thelesperma
Theobroma cacaoKNApSAcK Database
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tinospora cordifoliaKNApSAcK Database
Tinospora crispaPlant
Tragopogon porrifolius
Trichocereus candicansKNApSAcK Database
Trichocereus pachanoiKNApSAcK Database
Trichocereus spachianusKNApSAcK Database
Trigonella foenum-graecum
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiata
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Viscum albumKNApSAcK Database
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Xylopia parvifloraKNApSAcK Database
Zea mays L.
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
Zizyphus jujuba var. spinosaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Claviceps purpureaKNApSAcK Database
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
  • 2-arylethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 165 °CNot Available
Boiling Point277.00 to 278.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10.4 mg/mL at 15 °CNot Available
LogP3.894 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility5.72 g/LALOGPS
logP-0.14ALOGPS
logP0.68ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000306
DrugBank IDDB08841
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000433
KNApSAcK IDC00001435
Chemspider ID5408
KEGG Compound IDC00483
BioCyc IDTYRAMINE
BiGG ID35110
Wikipedia LinkTyramine
METLIN ID60
PubChem Compound5610
PDB IDNot Available
ChEBI ID15760
Good Scents IDrw1565911
References
General References
  1. Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
  2. Jacob G, Costa F, Vincent S, Robertson D, Biaggioni I: Neurovascular dissociation with paradoxical forearm vasodilation during systemic tyramine administration. Circulation. 2003 May 20;107(19):2475-9. Epub 2003 Apr 21. [PubMed:12707242 ]
  3. Nakai T, Yamada R: Basic and clinical reevaluation of tyramine and histamine tests for the investigation of adrenomedullary sympathetic functions. J Clin Endocrinol Metab. 1983 Jul;57(1):19-23. [PubMed:6853676 ]
  4. Jayanthi LD, Balasubramanian N, Balasubramanian AS: Cholinesterases exhibiting aryl acylamidase activity in human amniotic fluid. Clin Chim Acta. 1992 Feb 14;205(3):157-66. [PubMed:1349516 ]
  5. Watson DG, Midgley JM, Chen RN, Huang W, Bain GM, McDonald NM, Reid JL, McGhee CN: Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography-negative ion chemical ionization mass spectrometry (GC-NICIMS). J Pharm Biomed Anal. 1990;8(8-12):899-904. [PubMed:2100639 ]
  6. Chalon SA, Granier LA, Vandenhende FR, Bieck PR, Bymaster FP, Joliat MJ, Hirth C, Potter WZ: Duloxetine increases serotonin and norepinephrine availability in healthy subjects: a double-blind, controlled study. Neuropsychopharmacology. 2003 Sep;28(9):1685-93. Epub 2003 May 28. [PubMed:12784100 ]
  7. Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. [PubMed:319927 ]
  8. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
  9. Markianos E, Backman H: Diurnal changes in dopamine-beta-hydroxylase, homovanillic acid and 3-methoxy-4-hydroxyphenylglycol in serum of man. J Neural Transm. 1976;39(1-2):79-93. [PubMed:988114 ]
  10. Causon RC, Brown MJ: Measurement of tyramine in human plasma, utilising ion-pair extraction and high-performance liquid chromatography with amperometric detection. J Chromatogr. 1984 Sep 14;310(1):11-7. [PubMed:6501508 ]
  11. Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. [PubMed:9282832 ]
  12. Wolrath H, Forsum U, Larsson PG, Boren H: Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry. J Clin Microbiol. 2001 Nov;39(11):4026-31. [PubMed:11682525 ]
  13. Varma DR, Chemtob S: Endothelium- and beta-2 adrenoceptor-independent relaxation of rat aorta by tyramine and certain other phenylethylamines. J Pharmacol Exp Ther. 1993 Jun;265(3):1096-104. [PubMed:8389852 ]
  14. Gabastou JM, Nugon-Baudon L, Robert Y, Manuel C, Vaissade P, Bourgeon E, Sibeud M, Szylit O, Bourlioux P: [Digestive amines of bacterial origin and behavior disorders. Apropos of a case]. Pathol Biol (Paris). 1996 Apr;44(4):275-81. [PubMed:8763591 ]
  15. Hiroi T, Imaoka S, Funae Y: Dopamine formation from tyramine by CYP2D6. Biochem Biophys Res Commun. 1998 Aug 28;249(3):838-43. [PubMed:9731223 ]
  16. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  17. Antal EJ, Hendershot PE, Batts DH, Sheu WP, Hopkins NK, Donaldson KM: Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. J Clin Pharmacol. 2001 May;41(5):552-62. [PubMed:11361052 ]
  18. Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. [PubMed:15932098 ]
  19. Di Stefano AF, Rusca A: Pressor response to oral tyramine during co-administration with safinamide in healthy volunteers. Naunyn Schmiedebergs Arch Pharmacol. 2011 Dec;384(6):505-15. doi: 10.1007/s00210-011-0674-2. Epub 2011 Aug 19. [PubMed:21850574 ]