1.0 2010-04-08 22:04:34 UTC 2019-11-26 02:54:46 UTC FDB000429 Salsolinol Salsolinol is an endogenous catechol isoquinoline detected in humans. Salsolinol was detected in urine of parkinsonian patients administered with L-DOPA. This finding stimulated the studies on Salsolinol derivatives in the brain, and gave new aspects of the endogenous alkaloids, which had been considered to occur only in plants. In normal non-alcoholic subjects and alcoholics, Salsolinol and O-methylated Salsolinol were found in urine, cerebrospinal fluid and brains. Salsolinol has an asymmetric center at first position and exists as (R)- and (S)enantiomer. The (R)enantiomer of Salsolinol is predominant in urine from healthy volunteers. Only the (R)enantiomers of Salsolinol and N-methylated Salsolinol occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S)enantiomers were not detected. (R)salsolinol synthase catalyzes the enantio-selective synthesis of (R)Salsolinol and 1-carboxyl(R)Salsolinol from dopamine with acetaldehyde or pyruvic acid. The N-methylation of (R)salsolinol into N-methylsalsolinol (NMSal) is catalyzed by two N-methyltransferases with different optimum pH, at pH 7.0 and 8.4. NM(R)Salsolinol is enzymatically oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion (DMDHIQ+) by an oxidase sensitive to semicarbaside and also non-enzymatically by autoxidation. NM(R)Salsolinol and its precursor, dopamine, were found to occur selectively in the nigro-striatum, whereas (R)Salsolinol distributes uniformly among the brain regions. (PMID 14697894) [HMDB]. (+)-(R)-Salsolinol (+)-Salsolinol (R)-(+)-Salsolinol (R)-Salsolinol 1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 1,2,3,4-Tetrahydro-1-methyl-6,7-isoquinolinediol, 9CI Salsolinol C10H13NO2 179.2157 179.094628665 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol (+)-salsolinol 525-72-4 CC1NCCC2=C1C=C(O)C(O)=C2 InChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3 IBRKLUSXDYATLG-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 Dialkylamines Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds 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 Secondary aliphatic amine Secondary amine Tetrahydroisoquinoline Solid logp 0.16 ALOGPS logs -1.43 ALOGPS solubility 6.71e+00 g/l ALOGPS logp 0.96 ChemAxon pka_strongest_acidic 9.61 ChemAxon pka_strongest_basic 8.7 ChemAxon iupac 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol ChemAxon average_mass 179.2157 ChemAxon mono_mass 179.094628665 ChemAxon smiles CC1NCCC2=C1C=C(O)C(O)=C2 ChemAxon formula C10H13NO2 ChemAxon inchi InChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3 ChemAxon inchikey IBRKLUSXDYATLG-UHFFFAOYSA-N ChemAxon polar_surface_area 52.49 ChemAxon refractivity 51 ChemAxon polarizability 19.24 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23172 Specdb::CMs 38867 Specdb::CMs 157024 Specdb::MsIr 2285 Specdb::MsIr 2286 Specdb::MsIr 2287 Specdb::MsMs 10874 Specdb::MsMs 10875 Specdb::MsMs 10876 Specdb::MsMs 17546 Specdb::MsMs 17547 Specdb::MsMs 17548 Specdb::MsMs 445455 Specdb::MsMs 445456 Specdb::MsMs 445457 Specdb::MsMs 445458 Specdb::MsMs 447404 Specdb::MsMs 447405 Specdb::MsMs 447406 Specdb::MsMs 447407 Specdb::MsMs 2241892 Specdb::MsMs 2244025 Specdb::MsMs 2246037 Specdb::MsMs 2248166 Specdb::MsMs 2248238 Specdb::MsMs 2250115 Specdb::MsMs 2250312 Specdb::MsMs 2252104 Specdb::MsMs 2255122 Specdb::MsMs 2255441 Specdb::MsMs 2257064 Specdb::NmrOneD 149940 Specdb::NmrOneD 149941 Specdb::NmrOneD 149942 Specdb::NmrOneD 149943 Specdb::NmrOneD 149944 Specdb::NmrOneD 149945 Specdb::NmrOneD 149946 Specdb::NmrOneD 149947 Specdb::NmrOneD 149948 Specdb::NmrOneD 149949 Specdb::NmrOneD 149950 Specdb::NmrOneD 149951 Specdb::NmrOneD 149952 Specdb::NmrOneD 149953 Specdb::NmrOneD 149954 Specdb::NmrOneD 149955 Specdb::NmrOneD 149956 Specdb::NmrOneD 149957 Specdb::NmrOneD 149958 Specdb::NmrOneD 149959 HMDB05199 #<Reference:0x000055ce32384b80> #<Reference:0x000055ce32384978> #<Reference:0x000055ce32384770> 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 Cocoa bean Type 1 specific Theobroma cacao 3641 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Custard apple Type 1 specific Annona reticulata 301862 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 Anti-alcoholic 98 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Cardiac 764 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Hypertensive 1007