1.0 2011-09-21 00:26:19 UTC 2015-07-21 06:57:35 UTC FDB023207 (R)-N-Methylsalsolinol 1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [N-methyl-(R)salsolinol, NM(R)Sal] is the most potent toxin among isoquinolines. Endogenous isoquinolines with and without catechol structure have been proposed to be neurotoxins specific for dopamine neurons. (PMID 9085193) (R)salsolinol N-methyltransferase synthesizes N-methyl(R)salsolinol, which is further oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion by non-enzymatic and enzymatic oxidation. (PMID 14697894) Dopamine-derived N-methyl(R)salsolinol is an endogenous MPTP-like neurotoxin to cause Parkinson's disease. In the cerebrospinal fluid from newly diagnosed untreated patients with Parkinson's disease, the level of this toxin was found to increase significantly, compared to control and a disease control, multiple system atrophy. L-DOPA therapy did not seem to affect the level of this toxin. The results suggest that N-methyl(R)salsolinol level in the cerebrospinal fluid may indicate remaining dopamine neurons in the parkinsonian brain. (PMID 10076861) N-methyl(R)salsolinol (NM(R)Sal) induces apoptosis (but not necrosis) in SH-SY5Y cells, and the apoptotic cascade is initiated by mitochondrial permeability transition and activated by stepwise reactions. (PMID 12200198) [HMDB] N-Methyl-(R)-salsolinol C11H15NO2 193.2423 193.110278729 (1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol N-methyl-(R)-salsolinol 53622-84-7 C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12 InChI=1S/C11H15NO2/c1-7-9-6-11(14)10(13)5-8(9)3-4-12(7)2/h5-7,13-14H,3-4H2,1-2H3/t7-/m1/s1 RKMGOUZXGHZLBJ-SSDOTTSWSA-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 1.23 ALOGPS logs -0.94 ALOGPS solubility 2.19e+01 g/l ALOGPS logp 1.59 ChemAxon pka_strongest_acidic 6.92 ChemAxon pka_strongest_basic 10.24 ChemAxon iupac (1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol ChemAxon average_mass 193.2423 ChemAxon mono_mass 193.110278729 ChemAxon smiles C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12 ChemAxon formula C11H15NO2 ChemAxon inchi InChI=1S/C11H15NO2/c1-7-9-6-11(14)10(13)5-8(9)3-4-12(7)2/h5-7,13-14H,3-4H2,1-2H3/t7-/m1/s1 ChemAxon inchikey RKMGOUZXGHZLBJ-SSDOTTSWSA-N ChemAxon polar_surface_area 43.7 ChemAxon refractivity 56.29 ChemAxon polarizability 21.35 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10190 Specdb::CMs 38640 Specdb::CMs 162454 Specdb::MsIr 2019 Specdb::MsIr 2020 Specdb::MsIr 2021 Specdb::NmrOneD 28422 Specdb::NmrOneD 28423 Specdb::NmrOneD 28424 Specdb::NmrOneD 28425 Specdb::NmrOneD 28426 Specdb::NmrOneD 28427 Specdb::NmrOneD 28428 Specdb::NmrOneD 28429 Specdb::NmrOneD 28430 Specdb::NmrOneD 28431 Specdb::NmrOneD 28432 Specdb::NmrOneD 28433 Specdb::NmrOneD 28434 Specdb::NmrOneD 28435 Specdb::NmrOneD 28436 Specdb::NmrOneD 28437 Specdb::NmrOneD 28438 Specdb::NmrOneD 28439 Specdb::NmrOneD 28440 Specdb::NmrOneD 28441 Specdb::MsMs 288493 Specdb::MsMs 288494 Specdb::MsMs 288495 Specdb::MsMs 327634 Specdb::MsMs 327635 Specdb::MsMs 327636 Specdb::MsMs 2821655 Specdb::MsMs 2821656 Specdb::MsMs 2821657 Specdb::MsMs 2857428 Specdb::MsMs 2857429 Specdb::MsMs 2857430 HMDB03626 #<Reference:0x000055ce328d8a50> #<Reference:0x000055ce328d8870> #<Reference:0x000055ce328d8690> #<Reference:0x000055ce328d84b0> #<Reference:0x000055ce328d82d0> 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