1.0 2010-04-08 22:04:59 UTC 2025-11-18 22:31:42 UTC FDB001502 Glaucine Glaucine 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 . (+)-glaucine 1,2,9,10-Tetramethoxy-6a-alpha-aporphine 6a-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 ether Bromcholitin D-glaucine Glaucine fumarate Glaucine, (s)-isomer Glaucine,(d) Glauvent O,O-Dimethylisoboldine S-(+)-Glaucine C21H25NO4 355.4275 355.178358293 4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene 4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene 475-81-0 COC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3 InChI=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,6-8H2,1-5H3 RUZIUYOSRDWYQF-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. Aporphines Organic compounds Alkaloids and derivatives Aporphines Aromatic heteropolycyclic compounds Alkyl aryl ethers Anisoles Aralkylamines Azacyclic compounds Benzoquinolines Hydrocarbon derivatives Naphthalenes Organopnictogen compounds Phenanthrenes and derivatives Tetrahydroisoquinolines Trialkylamines Alkyl aryl ether Amine Anisole Aporphine Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Benzoquinoline Ether Hydrocarbon derivative Naphthalene Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenanthrene Quinoline Tertiary aliphatic amine Tertiary amine Tetrahydroisoquinoline logp 3.08 ALOGPS logs -4.21 ALOGPS solubility 2.21e-02 g/l ALOGPS logp 3.07 ChemAxon pka_strongest_basic 7.1 ChemAxon iupac 4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene ChemAxon average_mass 355.4275 ChemAxon mono_mass 355.178358293 ChemAxon smiles COC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3 ChemAxon formula C21H25NO4 ChemAxon inchi InChI=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,6-8H2,1-5H3 ChemAxon inchikey RUZIUYOSRDWYQF-UHFFFAOYSA-N ChemAxon polar_surface_area 40.16 ChemAxon refractivity 101.88 ChemAxon polarizability 40.02 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 75105 Specdb::MsMs 75106 Specdb::MsMs 75107 Specdb::MsMs 134670 Specdb::MsMs 134671 Specdb::MsMs 134672 Specdb::MsMs 3436384 Specdb::MsMs 3436385 Specdb::MsMs 3436386 Specdb::MsMs 3436387 Specdb::MsMs 3436388 Specdb::MsMs 3436389 Specdb::CMs 113295 Specdb::CMs 127008 Barley Type 1 specific Hordeum vulgare 4513 Custard apple Type 1 specific Annona reticulata 301862 Aldose reductase inhibitor 40 An 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).