1.02010-04-08 22:04:59 UTC2019-11-26 02:56:32 UTCFDB001502GlaucineGlaucine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Glaucine is practically insoluble (in water) and a very strong basic compound (based on its pKa). Glaucine can be found in barley and custard apple, which makes glaucine a potential biomarker for the consumption of these food products. Glaucine has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries. Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images, and has been detected as a novel psychoactive drug .(+)-glaucine1,2,9,10-Tetramethoxy-6a-alpha-aporphine6a-alpha-Aporphine, 1,2,9,10-tetramethoxy-6aα-Aporphine, 1,2,9,10-tetramethoxy-6aalpha-Aporphine, 1,2,9,10-tetramethoxy-6aalpha-Aporphine, 1,2,9,10-tetramethoxy- (8CI)Boldine dimethyl etherBromcholitinD-glaucineGlaucine fumarateGlaucine, (s)-isomerGlaucine,(d)GlauventO,O-DimethylisoboldineS-(+)-GlaucineC21H25NO4355.4275355.1783582934,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene475-81-0COC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3RUZIUYOSRDWYQF-UHFFFAOYSA-N belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.AporphinesOrganic compoundsAlkaloids and derivativesAporphinesAromatic heteropolycyclic compoundsAlkyl aryl ethersAnisolesAralkylaminesAzacyclic compoundsBenzoquinolinesHydrocarbon derivativesNaphthalenesOrganopnictogen compoundsPhenanthrenes and derivativesTetrahydroisoquinolinesTrialkylaminesAlkyl aryl etherAmineAnisoleAporphineAralkylamineAromatic heteropolycyclic compoundAzacycleBenzenoidBenzoquinolineEtherHydrocarbon derivativeNaphthaleneOrganic nitrogen compoundOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenanthreneQuinolineTertiary aliphatic amineTertiary amineTetrahydroisoquinolinelogp3.08logs-4.21solubility2.21e-02 g/llogp3.07pka_strongest_basic7.1iupac4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaeneaverage_mass355.4275mono_mass355.178358293smilesCOC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3formulaC21H25NO4inchiInChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3inchikeyRUZIUYOSRDWYQF-UHFFFAOYSA-Npolar_surface_area40.16refractivity101.88polarizability40.02rotatable_bond_count4acceptor_count5donor_count0physiological_charge1formal_charge0Specdb::CMs113295Specdb::CMs127008Specdb::MsMs75105Specdb::MsMs75106Specdb::MsMs75107Specdb::MsMs134670Specdb::MsMs134671Specdb::MsMs134672Specdb::MsMs3436384Specdb::MsMs3436385Specdb::MsMs3436386Specdb::MsMs3436387Specdb::MsMs3436388Specdb::MsMs3436389BarleyType 1specificHordeum vulgare4513Custard appleType 1specificAnnona reticulata301862aldose reductase inhibitor40An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).