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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
Substance
CAS Registry & name
Categories
Source
Drugs
*
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-