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Tetrahydroisoquinolines

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Definition: A group of ISOQUINOLINES in which the nitrogen containing ring is protonated. They derive from the non-enzymatic Pictet-Spengler condensation of CATECHOLAMINES with ALDEHYDES.     
Examples Salsoline Alkaloids; Toxiferine; Tubocurarine 		Other names Tetrahydro Isoquinolines; Tetrahydro-Isoquinolines; 1,2,3,4-Tetrahydroisoquinolines
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
4'-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)biphenyl-4-ol  0   *Biphenyl Compounds *Tetrahydroisoquinolines. Bioorg Med Chem. 2008 Apr 1;16(7):3732-43.
(S)-2-(2,4-hexadienoyl)-7-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid  0   *Tetrahydroisoquinolines PPAR alpha/agonists PPAR gamma/agonists. Chem Pharm Bull (Tokyo). 2011;59(7):876-9
renieramycin I  0   *Tetrahydroisoquinolines Alkaloids. Chem Pharm Bull (Tokyo). 2011;59(6):787-92
6,7-dimethoxy-2-(6-methoxynaphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline  0   *Tetrahydroisoquinolines Radiopharmaceuticals. Bioorg Med Chem. 2010 Sep 1;18(17):6489-95
(R)-1-(1H-indol-3-yl)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydroisoquinoline  0   *Indoles *Tetrahydroisoquinolines. J Org Chem. 2009 Mar 6;74(5):2018-27
N-(1-((4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)methyl)-2-methylpropyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide  0   *Piperidines *Tetrahydroisoquinolines Receptors, Opioid, kappa/antagonists & inhibitors. Psychopharmacology (Berl) 2010 Jun;210(2):189-98
N-(1-((4-(3-carbamoylphenyl)-3,4-dimethylpiperidin-1-yl)methyl)-2-methylpropyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide  0   *Piperidines *Tetrahydroisoquinolines Receptors, Opioid, kappa/antagonists & inhibitors. Psychopharmacology (Berl) 2010 Jun;210(2):189-98
7-hydroxy-N-(1-((4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)methyl)-2-methylbutyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide dihydrochloride  0   *Piperidines *Tetrahydroisoquinolines Receptors, Opioid, kappa/antagonists & inhibitors. Psychopharmacology (Berl) 2010 Jun;210(2):189-98
1,1'-(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline)  0   *Tetrahydroisoquinolines. Eur J Med Chem. 2010 Jul;45(7):3240-4
P91024  0   *Tetrahydroisoquinolines. Yao Xue Xue Bao. 2007 Nov;42(11):1176-82
Zalypsis  0   *Tetrahydroisoquinolines. Biochem Pharmacol 2009 Jul 15;78(2):162-70
7-isothiocyanatotetrahydroisoquinoline  0   *Tetrahydroisoquinolines. Bioorg Med Chem Lett 2009 Feb 15;19(4):1071-4
3-methyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline  0   *Tetrahydroisoquinolines. Med Chem 2008 Nov;4(6):531-8
3-methyl-1,2,3,4-tetrahydroisoquinoline  0   *Tetrahydroisoquinolines. Med Chem 2008 Nov;4(6):531-8
KV-5070  0   *Tetrahydroisoquinolines PPAR gamma/agonists. Naunyn Schmiedebergs Arch Pharmacol 2008 Jun;377(4-6):401-10
(1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid  0   *Tetrahydroisoquinolines. Eur J Med Chem. 2008 Jul;43(7):1552-8
N-(2-(3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)piperidinio)ethyl)-4-fluorobenzamide  0   *Tetrahydroisoquinolines. Eur J Drug Metab Pharmacokinet 2008 Apr-Jun;33(2):117-27
7-hydroxy-N-(1-((4-(3-hydroxyphenyl)-3,4-dimethyl-1--piperidinyl)methyl)-2-methylpropyl)-1,2,3,4-tetrahydro-2-methylisoquinolinecarboxamide  0   *Piperidines *Tetrahydroisoquinolines Carbon Radioisotopes. Nucl Med Biol 2008 Jul;35(5):561-9
AG525E1  0   *Amines *Tetrahydroisoquinolines. Bioorg Med Chem Lett 2008 Jun 1;18(11):3440-5
EDL-155  0   *Tetrahydroisoquinolines. Cancer Chemother Pharmacol 2008 May;61(6):1037-44
6,7-dimethoxytetrahydroisoquinoline  0   *Tetrahydroisoquinolines. Bioorg Med Chem 2008 Apr 1;16(7):3732-43
RESPIR 4-95  0   *Tetrahydroisoquinolines. Pulm Pharmacol Ther 2008;21(1):125-33
JNJ-28583867  0   *Tetrahydroisoquinolines. Eur J Pharmacol 2007 Dec 8;576(1-3):43-54
2-naphthylethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline  0   *Naphthalenes *Tetrahydroisoquinolines. J Pharmacol Exp Ther 2007 Feb;320(2):782-9
10-O-demethylcephaeline  0   *Terpenes *Tetrahydroisoquinolines Alkaloids. Phytochemistry. 2006 May;67(9):894-7
oceanalin A  0   *Glycosides *Tetrahydroisoquinolines. Org Lett 2005 Jul 7;7(14):2897-900
3-epi-jorumycin  0   *Tetrahydroisoquinolines. J Am Chem Soc. 2005 Sep 14;127(36):12684-90
3-epi-renieramycin G  0   *Tetrahydroisoquinolines. J Am Chem Soc. 2005 Sep 14;127(36):12684-90
jorumycin  0   *Tetrahydroisoquinolines. J Am Chem Soc. 2005 Sep 14;127(36):12684-90
renieramycin G  0   *Tetrahydroisoquinolines Alkaloids. J Am Chem Soc. 2005 Sep 14;127(36):12476-7
lemonomycinone  0   *Tetrahydroisoquinolines. J Am Chem Soc. 2005 Sep 14;127(36):12476-7
alangiside  0   *Glucosides *Monoterpenes *Tetrahydroisoquinolines. J Nat Prod 2005 Aug;68(8):1147-52
isocephaeline  0   *Terpenes *Tetrahydroisoquinolines. J Nat Prod 2005 Jun;68(6):947-50
PM 00104  0   *Tetrahydroisoquinolines Alkaloids. Rapid Commun Mass Spectrom 2005;19(5):689-95
N-methylcoculaurine  0   *Tetrahydroisoquinolines. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 25;806(1):75-8
1-(beta-naphthylmethyl)-6,7-dihydroxy-1,2,3,4-tetra-hydroisoquinoline  0   *Tetrahydroisoquinolines. Arzneimittelforschung. 2004;54(11):705-10; Thromb Res 2001 Nov 15;104(4):249-55
N,N'-bis-(2-carbamoyl-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolinyl)piperazine  0   *Piperazines *Tetrahydroisoquinolines. Chem Pharm Bull (Tokyo) 2004 Mar;52(3):316-21
renieramycin O  0   *Tetrahydroisoquinolines. J Nat Prod 2004 Jun;67(6):1023-8
renieramycin N  0   *Tetrahydroisoquinolines Alkaloids. J Nat Prod 2003 Nov;66(11):1441-6
renieramycin M  0   *Tetrahydroisoquinolines Alkaloids. J Nat Prod 2003 Nov;66(11):1441-6
lemonomycin  0   *Tetrahydroisoquinolines. J Am Chem Soc. 2003 Dec 10;125(49):15000-1
renieramycin J  0   *Tetrahydroisoquinolines Alkaloids. J Nat Prod 2003 Aug;66(8):1136-9
1-(1-adamantyl)-2-(4-(2-chloropyrimidinyl))-1,2,3,4-tetrahydroisoquinoline  0   *Pyrimidines *Tetrahydroisoquinolines. Acta Pol Pharm. 1990;47(3-4):59-62
1-naphthylethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline  0   *Naphthalenes *Tetrahydroisoquinolines. Biochem Pharmacol 2003 Feb 1;65(3):457-64
2-acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline  0   *Tetrahydroisoquinolines Receptors, AMPA/antagonists & inhibitors. J Med Chem 2003 Jan 2;46(1):197-200
N-(1,2,3,4-tetrahydroisoquinolinium-3-ylcarbonyl)-1-(4-chlorobenzyl)-2-(4-cyclohexyl-4-(1H-1,2,4-triazol-1-ylmethyl)piperidin-1-yl)-2-oxoethylamine  0   *Triazoles *Tetrahydroisoquinolines. J Med Chem 2002 Oct 10;45(21):4589-93
NS-417 cpd  0   *Oximes *Tetrahydroisoquinolines. Neurochem Res 2002 Feb;27(1-2):107-11
tyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-phenylalanyl-4-bromoacetamidophenylalanine  0   *Oligopeptides *Tetrahydroisoquinolines. J Med Chem 2002 Aug 29;45(18):3820-3
N-(2-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione  0   *Tetrahydroisoquinolines. Acta Crystallogr C 2002 Mar;58( Pt 3):o164-7
N-(2-bromo-4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione  0   *Tetrahydroisoquinolines. Acta Crystallogr C 2002 Mar;58( Pt 3):o164-7
N-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione  0   *Tetrahydroisoquinolines. Acta Crystallogr C 2002 Mar;58( Pt 3):o164-7
5,6,7,8-tetrahydro-1,3-dioxolo(4,5-g)isoquinoline  0   *Tetrahydroisoquinolines. Pharmacol Biochem Behav 2002 Jan-Feb;71(1-2):205-13
2-(5-bromo-2,3-dimethoxyphenyl)-4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolinomethyl)imidazole  0   *Imidazoles *Tetrahydroisoquinolines. Bioorg Med Chem. 2001 Dec;9(12):3113-22
N-hydroxy-2-((2,2-difluoroethoxy)(4-methoxyphenyl)phosphoryl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide  0   *Hydroxylamines *Tetrahydroisoquinolines Metalloendopeptidases/antagonists & inhibitors. J Med Chem 2002 Feb 14;45(4):930-6
N-hydroxy-2-((2,2,2-trifluoroethoxy)(4-methoxyphenyl)phosphoryl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide  0   *Hydroxylamines *Tetrahydroisoquinolines Metalloendopeptidases/antagonists & inhibitors. J Med Chem 2002 Feb 14;45(4):930-6
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid  0   *Dipeptides *Tetrahydroisoquinolines Ligands Receptors, Opioid, delta/antagonists & inhibitors. J Med Chem 2002 Jan 31;45(3):713-20
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-glycine N-benzylamide  0   *Oligopeptides *Tetrahydroisoquinolines Ligands Receptors, Opioid, mu/agonists Receptors, Opioid, delta/antagonists & inhibitors. J Med Chem 2002 Jan 31;45(3):713-20
1,2,3,4-tetrahydro-7-methoxyisoquinoline-3-carboxylic acid  0   *Tetrahydroisoquinolines. J Org Chem 2001 Nov 16;66(23):7575-87
4-((2-amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxy)methyl)-1-(4-pyridinyl)piperidine-4-carboxylic acid monomethanesulfonate trihydrate  0   *Piperidines *Pyridines *Tetrahydroisoquinolines Factor Xa/antagonists & inhibitors. Eur J Pharmacol 2001 Oct 5;428(2):163-8
solifenacin succinate  0   *Quinuclidines *Tetrahydroisoquinolines.
Pharma Action Muscarinic Antagonists 		Gen Pharmacol 2000 Aug;35(2):71-5SOLIFENACIN SUCCINATE
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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