1.0 2010-04-08 22:10:20 UTC 2020-09-17 15:29:59 UTC FDB012750 Hordenine Hordenine 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)phenol 4-(2-Dimethylaminoethyl)phenol, 9CI 4-[2-(Dimethylamino)ethyl]phenol 4-Hydroxy-N,N-dimethylphenethylamine Anhalin Anhaline Cactine Eremursine Hordenin Hordetin N-Dimethyltyramine N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine N,N-Dimethyl-4-hydroxy-&beta;-phenethylamine N,N-Dimethyl-4-hydroxy-b-phenethylamine N,N-Dimethyl-4-hydroxy-beta-phenethylamine N,N-Dimethyl-4-hydroxy-β-phenethylamine N,n-dimethyl-p-hydroxyphenethylamine N,n-dimethyltyramine Ordenina Ordenine p-(2-Dimethylaminoethyl)phenol p-[2-(Dimethylamino)ethyl]phenol P-hydroxy-n,n-dimethylphenethylamine Peyocactine Phenol, 4-[2-(dimethylamino)ethyl]- Phenol, p-[2-(dimethylamino)ethyl]- C10H15NO 165.2322 165.115364107 4-[2-(dimethylamino)ethyl]phenol hordenine 539-15-1 CN(C)CCC1=CC=C(O)C=C1 InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 KUBCEEMXQZUPDQ-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. Phenethylamines Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds Trialkylamines 1-hydroxy-2-unsubstituted benzenoid Amine Aralkylamine Aromatic homomonocyclic compound Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenethylamine Phenol Tertiary aliphatic amine Tertiary amine Tyramine derivatives phenethylamine alkaloid Solid logp 1.76 ALOGPS logs -0.75 ALOGPS solubility 2.97e+01 g/l ALOGPS melting_point Mp 118° logp 1.63 ChemAxon pka_strongest_acidic 10.31 ChemAxon pka_strongest_basic 9.19 ChemAxon iupac 4-[2-(dimethylamino)ethyl]phenol ChemAxon average_mass 165.2322 ChemAxon mono_mass 165.115364107 ChemAxon smiles CN(C)CCC1=CC=C(O)C=C1 ChemAxon formula C10H15NO ChemAxon inchi InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 ChemAxon inchikey KUBCEEMXQZUPDQ-UHFFFAOYSA-N ChemAxon polar_surface_area 23.47 ChemAxon refractivity 51.34 ChemAxon polarizability 19.35 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5952 Specdb::CMs 38757 Specdb::CMs 136187 Specdb::CMs 143921 Specdb::NmrOneD 48242 Specdb::NmrOneD 48243 Specdb::NmrOneD 48244 Specdb::NmrOneD 48245 Specdb::NmrOneD 48246 Specdb::NmrOneD 48247 Specdb::NmrOneD 48248 Specdb::NmrOneD 48249 Specdb::NmrOneD 48250 Specdb::NmrOneD 48251 Specdb::NmrOneD 48252 Specdb::NmrOneD 48253 Specdb::NmrOneD 48254 Specdb::NmrOneD 48255 Specdb::NmrOneD 48256 Specdb::NmrOneD 48257 Specdb::NmrOneD 48258 Specdb::NmrOneD 48259 Specdb::NmrOneD 48260 Specdb::NmrOneD 48261 Specdb::MsIr 2208 Specdb::MsIr 2209 Specdb::MsIr 2210 Specdb::MsMs 58686 Specdb::MsMs 58687 Specdb::MsMs 58688 Specdb::MsMs 114675 Specdb::MsMs 114676 Specdb::MsMs 114677 Specdb::MsMs 1470827 Specdb::MsMs 1470942 Specdb::MsMs 1470943 Specdb::MsMs 1470944 Specdb::MsMs 1471027 Specdb::MsMs 1471032 Specdb::MsMs 1471033 Specdb::MsMs 1471034 Specdb::MsMs 1471035 Specdb::MsMs 1471036 Specdb::MsMs 1471037 Specdb::MsMs 1471038 Specdb::MsMs 1471039 Specdb::MsMs 1471040 Specdb::MsMs 1471041 Specdb::MsMs 1471042 Specdb::MsMs 1471043 Specdb::MsMs 1471044 Specdb::MsMs 1471045 HMDB04366 5764 #<Reference:0x000055ce3030cb00> Barley Type 1 specific Hordeum vulgare 4513 6.3 6.3 6.3 mg/100 g Breakfast cereal Type 2 specific Cereals and cereal products Unknown generic Corn Type 1 specific Zea mays 4577 Oat Type 1 specific Avena sativa 4498 Sweet orange Type 1 specific Citrus sinensis 2711 Tamarind Type 1 specific Tamarindus indica 58860 Anti feedant 275 Anti-asthmatic 134 A drug used to treat asthma. Anti-diarrheic 229 Any drug found useful in the symptomatic treatment of diarrhoea. Broncho elaxant 740 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Cardiotonic 771 A 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. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Vasoconstrictor 1412 Drug used to cause constriction of the blood vessels.