1.02010-04-08 22:10:20 UTC2020-09-17 15:29:59 UTCFDB012750HordenineHordenine 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, a strong basic compound, is a colorless solid that is soluble in organic solvents. Hordenine is biosynthesized by the stepwise N-methylation of tyramine, which is first converted to N-methyltyramine by tyramine N-methyltransferase and then is methylated to hordenine (PMID: 24257763). Hordenine exists in all living organisms, ranging from plants to humans. It is found in highest concentrations with barley (Hordeum species), from which its name is derived. Several varieties of plants in the family Cactacea (cacti) produce hordenine which, as a potent phenylethylamine alkaloid, has antibacterial and antibiotic properties (PMID: 30609368; PMID: 30128579). Hordenine has been found in several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds making it a potential biomarker for the consumption of these foods. People consuming beer brewed from barley will have higher levels of hordenine. However, hordenine in urine interferes with tests for morphine, heroin and other opioid drugs (PMID: 1618458). Hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system and can promote weight loss by enhancing metabolism.3595-05-9 (unspecified sulfate)4-(2-Dimethylaminoethyl)phenol4-(2-Dimethylaminoethyl)phenol, 9CI4-[2-(Dimethylamino)ethyl]phenol4-Hydroxy-N,N-dimethylphenethylamineAnhalinAnhalineCactineEremursineHordeninHordetinN-DimethyltyramineN,N-Dimethyl-2-(4-hydroxyphenyl)ethylamineN,N-Dimethyl-4-hydroxy-β-phenethylamineN,N-Dimethyl-4-hydroxy-b-phenethylamineN,N-Dimethyl-4-hydroxy-beta-phenethylamineN,N-Dimethyl-4-hydroxy-β-phenethylamineN,n-dimethyl-p-hydroxyphenethylamineN,n-dimethyltyramineOrdeninaOrdeninep-(2-Dimethylaminoethyl)phenolp-[2-(Dimethylamino)ethyl]phenolP-hydroxy-n,n-dimethylphenethylaminePeyocactinePhenol, 4-[2-(dimethylamino)ethyl]-Phenol, p-[2-(dimethylamino)ethyl]-C10H15NO165.2322165.1153641074-[2-(dimethylamino)ethyl]phenolhordenine539-15-1CN(C)CCC1=CC=C(O)C=C1InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3KUBCEEMXQZUPDQ-UHFFFAOYSA-N 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.PhenethylaminesOrganic compoundsBenzenoidsBenzene and substituted derivativesPhenethylaminesAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoidsAralkylaminesHydrocarbon derivativesOrganooxygen compoundsOrganopnictogen compoundsTrialkylamines1-hydroxy-2-unsubstituted benzenoidAmineAralkylamineAromatic homomonocyclic compoundHydrocarbon derivativeOrganic nitrogen compoundOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenethylaminePhenolTertiary aliphatic amineTertiary amineTyramine derivativesphenethylamine alkaloidSolidlogp1.76logs-0.75solubility2.97e+01 g/lmelting_pointMp 118°logp1.63pka_strongest_acidic10.31pka_strongest_basic9.19iupac4-[2-(dimethylamino)ethyl]phenolaverage_mass165.2322mono_mass165.115364107smilesCN(C)CCC1=CC=C(O)C=C1formulaC10H15NOinchiInChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3inchikeyKUBCEEMXQZUPDQ-UHFFFAOYSA-Npolar_surface_area23.47refractivity51.34polarizability19.35rotatable_bond_count3acceptor_count2donor_count1physiological_charge1formal_charge0Specdb::MsIr2208Specdb::MsIr2209Specdb::MsIr2210Specdb::NmrOneD48242Specdb::NmrOneD48243Specdb::NmrOneD48244Specdb::NmrOneD48245Specdb::NmrOneD48246Specdb::NmrOneD48247Specdb::NmrOneD48248Specdb::NmrOneD48249Specdb::NmrOneD48250Specdb::NmrOneD48251Specdb::NmrOneD48252Specdb::NmrOneD48253Specdb::NmrOneD48254Specdb::NmrOneD48255Specdb::NmrOneD48256Specdb::NmrOneD48257Specdb::NmrOneD48258Specdb::NmrOneD48259Specdb::NmrOneD48260Specdb::NmrOneD48261Specdb::CMs5952Specdb::CMs38757Specdb::CMs136187Specdb::CMs143921Specdb::MsMs1471425Specdb::MsMs2231248Specdb::MsMs2232975Specdb::MsMs2253969Specdb::MsMs1470827Specdb::MsMs1470942Specdb::MsMs1470943Specdb::MsMs1470944Specdb::MsMs1471027Specdb::MsMs1471032Specdb::MsMs1471033Specdb::MsMs1471034Specdb::MsMs1471035Specdb::MsMs1471036Specdb::MsMs1471037Specdb::MsMs1471038Specdb::MsMs1471039Specdb::MsMs1471040Specdb::MsMs1471041Specdb::MsMs1471042Specdb::MsMs1471043Specdb::MsMs1471044Specdb::MsMs1471045Specdb::MsMs1471046Specdb::MsMs1471047HMDB043665764#<Reference:0x00005556755506d8>BarleyType 1specificHordeum vulgare45136.36.36.3mg/100 gBreakfast cerealType 2specificCereals and cereal productsUnknowngenericCornType 1specificZea mays4577OatType 1specificAvena sativa4498Sweet orangeType 1specificCitrus sinensis2711TamarindType 1specificTamarindus indica58860anti asthmatic134A drug used to treat asthma.anti diarrheic229Any drug found useful in the symptomatic treatment of diarrhoea.anti feedant275broncho elaxant740Any substance introduced into a living organism with therapeutic or diagnostic purpose.cardiotonic771A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.hepatoprotective981Any compound that is able to prevent damage to the liver.pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.vasoconstrictor1412Drug used to cause constriction of the blood vessels.