1.0 2010-04-08 22:09:40 UTC 2019-11-26 03:04:58 UTC FDB011478 Narcotoline Alkaloid from straw of Papaver somniferum (opium poppy) Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media. It can be obtained from the opium poppy Papaver somniferum. It is present at much higher levels in strains used for culinary purposes (poppyseed production) than in high-morphine strains used for opium production. Narcotoline is found in opium poppy. Narcotoline C21H21NO7 399.3939 399.131802031 3-{4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one 3-{4-hydroxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-3H-2-benzofuran-1-one 521-40-4 COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12 InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3 LMGZCSKYOKDBES-UHFFFAOYSA-N belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. Phthalide isoquinolines Organic compounds Alkaloids and derivatives Phthalide isoquinolines Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Acetals Alkyl aryl ethers Amino acids and derivatives Anisoles Aralkylamines Azacyclic compounds Benzodioxoles Benzofuranones Carboxylic acid esters Hydrocarbon derivatives Lactones Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Oxacyclic compounds Phthalides Tetrahydroisoquinolines Trialkylamines 1-hydroxy-4-unsubstituted benzenoid Acetal Alkyl aryl ether Amine Amino acid or derivatives Anisole Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Benzodioxole Benzofuranone Carboxylic acid derivative Carboxylic acid ester Ether Hydrocarbon derivative Isobenzofuranone Isocoumaran Lactone Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Phthalide Phthalide isoquinoline Tertiary aliphatic amine Tertiary amine Tetrahydroisoquinoline logp 1.98 ALOGPS logs -2.94 ALOGPS solubility 4.63e-01 g/l ALOGPS melting_point Mp 202° (189°) logp 1.42 ChemAxon pka_strongest_acidic 6.1 ChemAxon pka_strongest_basic 10.31 ChemAxon iupac 3-{4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one ChemAxon average_mass 399.3939 ChemAxon mono_mass 399.131802031 ChemAxon smiles COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12 ChemAxon formula C21H21NO7 ChemAxon inchi InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3 ChemAxon inchikey LMGZCSKYOKDBES-UHFFFAOYSA-N ChemAxon polar_surface_area 86.69 ChemAxon refractivity 102.59 ChemAxon polarizability 40.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 7142 Specdb::MsMs 7143 Specdb::MsMs 7144 Specdb::MsMs 13814 Specdb::MsMs 13815 Specdb::MsMs 13816 Specdb::MsMs 3046363 Specdb::MsMs 3046364 Specdb::MsMs 3046365 Specdb::MsMs 3094270 Specdb::MsMs 3094271 Specdb::MsMs 3094272 Specdb::CMs 10817 Specdb::CMs 43291 Specdb::CMs 151317 HMDB33440 #<Reference:0x000055ce31f2f378> Opium poppy Type 1 specific Papaver somniferum 3469