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Record Information
Version1.0
Created at2006-05-22 15:12:12 UTC
Updated at2021-10-07 20:40:53 UTC
NP-MRD IDNP0001065
Secondary Accession NumbersNone
Natural Product Identification
Common NameTheobromine
DescriptionTheobromine, or 3,7-Dimethylxanthine, is the principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine. Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus.
Structure
Thumb
Synonyms
ValueSource
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dioneChEBI
3,7-Dimethylpurine-2,6-dioneChEBI
3,7-DimethylxanthineChEBI
TheobrominChEBI
TeobrominHMDB
2,6-Dihydroxy-3,7-dimethyl-purineHMDB
3,7-Dimethyl-xanthineHMDB
DiurobromineHMDB
Chemical FormulaC7H8N4O2
Average Mass180.1640 Da
Monoisotopic Mass180.06473 Da
IUPAC Name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheobromine
CAS Registry Number83-67-0
SMILES
CN1C=NC2=C1C(O)=NC(=O)N2C
InChI Identifier
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChI KeyYAPQBXQYLJRXSA-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)V.dorna832021-08-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)Varshavi.d262021-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Varshavi.d262021-08-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensis
Agaricus bisporus
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchos
AnatidaeFooDB
Anethum graveolens
Angelica keiskei
AnguillaFooDB
AnguilliformesFooDB
Annona cherimola
Annona muricataFooDB
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinum
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilisFooDB
Artocarpus heterophyllus
Asparagus officinalisFooDB
AstacideaFooDB
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella alba
Benincasa hispida
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalis
Bos taurusFooDB
Bos taurus X Bison bison
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napus
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italica
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridis
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensis
Brassica rapa var. rapaFooDB
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
BuccinidaeFooDB
Byrsonima crassifolia
Cajanus cajan
Camellia irawadiensisKNApSAcK Database
Camellia irrawadiensisKNApSAcK Database
Camellia ptilophyllaKNApSAcK Database
Camellia sinensisKNApSAcK Database
Camellia taliensisKNApSAcK Database
Camellia theaKNApSAcK Database
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpa
Carthamus tinctorius
Carum carviFooDB
Carya
Carya illinoinensisFooDB
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chondrus crispusFooDB
Chrysanthemum coronarium
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonKNApSAcK Database
Citrus maximaKNApSAcK Database
Citrus paradisiKNApSAcK Database
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clupea harengus harengusFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraKNApSAcK Database
Coffea dewevreiKNApSAcK Database
Coffea eugeniodesKNApSAcK Database
Coffea kianjavatensisKNApSAcK Database
Coffea libericaKNApSAcK Database
Coffea racemosaKNApSAcK Database
Coffea salvatrixKNApSAcK Database
Cola acuminataKNApSAcK Database
Cola sp.KNApSAcK Database
Colocasia esculentaFooDB
Columba
ColumbidaeFooDB
Corchorus olitorius
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosa
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferus
Cucumis sativus L.FooDB
Cucurbita
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Cyprinus carpioFooDB
Daucus carota
Daucus carota ssp. sativus
Dimocarpus longan
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
Diospyros
Diospyros kakiFooDB
Diospyros virginiana
Dromaius novaehollandiaeFooDB
Durio zibethinus
Dysphania ambrosioides
ElaeisFooDB
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
EngraulidaeFooDB
Engraulis encrasicolusFooDB
Equus caballus
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanica
Eugenia uniflora
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassa
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Gallus gallus
Garcinia mangostana
GastropodaFooDB
Gaylussacia baccata
Ginkgo biloba
Glycine maxFooDB
Gossypium
Grifola frondosaFooDB
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosusFooDB
Herreania sp.-
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoides
Homarus americanusFooDB
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.
Ictalurus punctatusFooDB
Ilex paraguariensis A.St.-Hil.KNApSAcK Database
Ilex peradoKNApSAcK Database
Illicium verumFooDB
Ipomoea aquatica
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativa
Lagenaria sicerariaFooDB
Lagopus muta
LaminariaFooDB
Lathyrus sativus
Laurus nobilis L.
Lens culinarisFooDB
Lentinus edodes
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidus
Levisticum officinale
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiaca
LupinusFooDB
Lupinus albus
LutjanidaeFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginata
Malus
Malus pumilaFooDB
Mammea americana
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapota
Maranta arundinacea
Matricaria recutitaFooDB
Matteuccia struthiopteris
Medicago sativaFooDB
Melanitta fusca
Meleagris gallopavoFooDB
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Merlangius merlangusFooDB
Mespilus germanica
Metroxylon sagu
Micropogonias undulatusFooDB
Microstomus kittFooDB
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Mugil cephalusFooDB
Musa acuminataFooDB
Musa x paradisiaca
Myrica
Myristica fragransFooDB
MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nucifera
Nephelium lappaceum
NephropidaeFooDB
Numida meleagris
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Odocoileus
Oenothera biennis
Olea europaea
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Opuntia
Opuntia cochenilliferaFooDB
Opuntia macrorhiza
Origanum majoranaFooDB
Origanum onites
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryctolagus
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Ovis aries
Pachyrhizus erosusFooDB
Panax ginseng
Pangium edule
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Paullinia cupanaKNApSAcK Database
Paullinia pachycarpaKNApSAcK Database
Paullinia trifoliataKNApSAcK Database
Paullinia yocoKNApSAcK Database
PectinidaeFooDB
Pediomelum esculentum
PerciformesFooDB
Perideridia oregana
Persea americanaFooDB
Petasites japonicus
Petroselinum crispumFooDB
Phaseolus coccineus
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicus
Phoenix dactylifera
Photinia melanocarpa
Phyllostachys edulisFooDB
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulis
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
Pollachius pollachiusFooDB
Polygonum alpinum
Portulaca oleraceaFooDB
Pouteria sapota
Prunus armeniacaFooDB
Prunus avium
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcisFooDB
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Pseudopiptadenia leptostachyaKNApSAcK Database
Psidium cattleianum
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communis
Pyrus pyrifoliaFooDB
Quercus
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativus
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrumFooDB
Ribes uva-crispaFooDB
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
Scomberomorus maculatusFooDB
Scorzonera hispanica
Scurrula atropurpureaKNApSAcK Database
Scurrura atropurpurea-
SebastesFooDB
Sebastes alutusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucuparia
Sorghum bicolor
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
StrombidaeFooDB
Struthio camelusFooDB
Sus scrofa
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cumini
Syzygium jambos
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
Thelesperma
Theobroma-
Theobroma cacaoKNApSAcK Database
Theobroma grandiflorumKNApSAcK Database
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordata
Tilia L.
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifolius
Trigonella foenum-graecum
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum spelta
Triticum turanicum
Typha angustifolia
Undaria pinnatifidaFooDB
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarponFooDB
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
VanillaFooDB
Verbena officinalis
Viburnum edule
Vicia fabaFooDB
Vigna aconitifolia
Vigna angularis
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalis
Virola surinamensisFooDB
VitisFooDB
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquatica
Ziziphus zizyphus
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point357 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 mg/mL at 25 °CNot Available
LogP-0.78Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility9.74 g/LALOGPS
logP-0.78ALOGPS
logP-0.77ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002825
DrugBank IDDB01412
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000455
KNApSAcK IDC00001509
Chemspider ID5236
KEGG Compound IDC07480
BioCyc ID3-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkTheobromine
METLIN ID1456
PubChem Compound5429
PDB IDNot Available
ChEBI ID28946
Good Scents IDrw1036961
References
General References
  1. Holstege A, Kurz M, Weinbeck M, Gerok W: Excretion of caffeine and its primary degradation products into bile. J Hepatol. 1993 Jan;17(1):67-73. [PubMed:8445222 ]
  2. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600. [PubMed:9847011 ]
  3. Blanchard J, Weber CW, Shearer LE: Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. Biopharm Drug Dispos. 1992 Apr;13(3):187-96. [PubMed:1576327 ]
  4. Sachse C, Ruschen S, Dettling M, Schley J, Bauer S, Muller-Oerlinghausen B, Roots I, Brockmoller J: Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. Clin Pharmacol Ther. 1999 Oct;66(4):431-8. [PubMed:10546928 ]
  5. Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8. [PubMed:591601 ]
  6. Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55. [PubMed:6617078 ]
  7. Tserng KY, King KC, Takieddine FN: Theophylline metabolism in premature infants. Clin Pharmacol Ther. 1981 May;29(5):594-600. [PubMed:7214789 ]
  8. Gonzalez-Jimenez J, Frutos G, Cayre I: Fluorescence quenching of human serum albumin by xanthines. Biochem Pharmacol. 1992 Aug 18;44(4):824-6. [PubMed:1510729 ]
  9. Sommer KR, Hill RM, Horning MG: Identification and quantification of drugs in human amniotic fluid. Res Commun Chem Pathol Pharmacol. 1975 Nov;12(3):583-95. [PubMed:1197933 ]
  10. Skopinska-Rozewska E, Janik P, Przybyszewska M, Sommer E, Bialas-Chromiec B: Inhibitory effect of theobromine on induction of angiogenesis and VEGF mRNA expression in v-raf transfectants of human urothelial cells HCV-29. Int J Mol Med. 1998 Dec;2(6):649-52. [PubMed:9850731 ]
  11. Resman BH, Blumenthal P, Jusko WJ: Breast milk distribution of theobromine from chocolate. J Pediatr. 1977 Sep;91(3):477-80. [PubMed:894424 ]
  12. Scott NR, Chakraborty J, Marks V: Determination of caffeine, theophylline and theobromine in serum and saliva using high-performance liquid chromatography. Ann Clin Biochem. 1984 Mar;21 ( Pt 2):120-4. [PubMed:6712142 ]
  13. Emara S: Simultaneous determination of caffeine, theophylline and theobromine in human plasma by on-line solid-phase extraction coupled to reversed-phase chromatography. Biomed Chromatogr. 2004 Oct;18(8):479-85. [PubMed:15386526 ]
  14. Gennaro MC, Abrigo C, Biglino P: Quantification of theophylline in human plasma by reversed-phase ion-interaction high-performance liquid chromatography and comparison with the TDx fluorescence polarization immunoassay procedure. Analyst. 1992 Jul;117(7):1071-4. [PubMed:1524227 ]
  15. Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63. [PubMed:8280834 ]
  16. Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17. [PubMed:15548587 ]