1.0 2011-09-21 00:14:38 UTC 2015-07-21 06:57:14 UTC FDB022477 2(N)-Methyl-norsalsolinol 2(N)-methyl-norsalsolinol (NMNorsal) is a dihydroxylated tetrahydroisoquinoline derivative 2(N)-analogue of salsolinol, identified as a putative endogenous neurotoxin in patients with Parkinson's disease. A prominent blood-brain barrier (BBB) is described to exist for salsolinol, but penetration of NMNorsal occurs through the BBB into the caudate nucleus of the rat brain. There was no alteration in extracellular dopamine or 3,4-dihydroxyphenylacetic acid levels. (PMID 11924888) 2(N)-methyl-norsalsolinol was identified in L-DOPA-treated patients with Parkinson's disease and proposed to be responsible for behavioral changes. Atypical heterocyclic L-DOPA/dopamine metabolite NMNorsal is able to modify long-term regulation of serotonin and opioid receptor expression in striatum. Since the occurrence of hallucinosis or psychosis following L-DOPA treatment is related to the serotonergic system, these results probably reflect a link between NMNorsal and L-DOPA side effects in Parkinson's disease. (PMID 14607311) [HMDB] 1,2,3,4-Tetrahydro-2-methyl-6,7-isoquinolinediol 2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline C10H13NO2 179.2157 179.094628665 2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol 2(N)-methyl-norsalsolinol 63937-92-8 CN1CCC2=CC(O)=C(O)C=C2C1 InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3 WETXYFNVBDLWIW-UHFFFAOYSA-N belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Tetrahydroisoquinolines Organic compounds Organoheterocyclic compounds Tetrahydroisoquinolines Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Azacyclic compounds Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds Trialkylamines 1-hydroxy-2-unsubstituted benzenoid Amine Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Tertiary aliphatic amine Tertiary amine Tetrahydroisoquinoline Solid logp 0.59 ALOGPS logs -0.68 ALOGPS solubility 3.71e+01 g/l ALOGPS logp 1.35 ChemAxon pka_strongest_acidic 9.43 ChemAxon pka_strongest_basic 7.47 ChemAxon iupac 2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol ChemAxon average_mass 179.2157 ChemAxon mono_mass 179.094628665 ChemAxon smiles CN1CCC2=CC(O)=C(O)C=C2C1 ChemAxon formula C10H13NO2 ChemAxon inchi InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3 ChemAxon inchikey WETXYFNVBDLWIW-UHFFFAOYSA-N ChemAxon polar_surface_area 43.7 ChemAxon refractivity 51.87 ChemAxon polarizability 19.56 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 146750 Specdb::NmrOneD 146751 Specdb::NmrOneD 146752 Specdb::NmrOneD 146753 Specdb::NmrOneD 146754 Specdb::NmrOneD 146755 Specdb::NmrOneD 146756 Specdb::NmrOneD 146757 Specdb::NmrOneD 146758 Specdb::NmrOneD 146759 Specdb::NmrOneD 146760 Specdb::NmrOneD 146761 Specdb::NmrOneD 146762 Specdb::NmrOneD 146763 Specdb::NmrOneD 146764 Specdb::NmrOneD 146765 Specdb::NmrOneD 146766 Specdb::NmrOneD 146767 Specdb::NmrOneD 146768 Specdb::NmrOneD 146769 Specdb::CMs 19721 Specdb::CMs 37966 Specdb::CMs 171649 Specdb::MsIr 1124 Specdb::MsIr 1125 Specdb::MsIr 1126 Specdb::MsMs 309874 Specdb::MsMs 309875 Specdb::MsMs 309876 Specdb::MsMs 354424 Specdb::MsMs 354425 Specdb::MsMs 354426 Specdb::MsMs 2409976 Specdb::MsMs 2409977 Specdb::MsMs 2409978 Specdb::MsMs 2555551 Specdb::MsMs 2555552 Specdb::MsMs 2555553 HMDB01189 #<Reference:0x000055ce31f5fb40> #<Reference:0x000055ce31f5f988> #<Reference:0x000055ce31f5f7d0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823