Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H11N |
| Molecular Weight | 133.1903 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CC2=C(CN1)C=CC=C2
InChI
InChIKey=UWYZHKAOTLEWKK-UHFFFAOYSA-N
InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
The tetrahydroisoquinoline nucleus is present in a number of compounds and drugs. Tetrahydroisoquinolines (THIQs), which belong to a group of cyclized condensation adducts of biogenic amines with aldehydes, are referred to as mammalian alkaloids. They include salsolinol (1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline; SAL) and tetrahydropapaveroline (6,7-dihydroxy-1-(3',4'-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline; THP) that are derived from dopamine through condensation with acetaldehyde and dopaldehyde (3,4-dihydroxyphenylacetaldehyde), respectively. THP is a putative dopaminergic neurotoxin that is implicated in the pathology of Parkinson's disease. It is known that THP is detected at a high level in the brain and the urine of parkinsonian patients under 3,4-dihydroxyphenylalanine (L-DOPA) therapy. In addition, significant levels of THP have also been detected in the brain after ethanol uptake and/or L-DOPA treatment, and this endogenous alkaloid is considered to account for the neurobehavioral abnormalities associated with alcoholism and may act as a neurotransmitter
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers. | 2005-02-15 |
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| Selective estrogen receptor modulators with conformationally restricted side chains. Synthesis and structure-activity relationship of ERalpha-selective tetrahydroisoquinoline ligands. | 2005-01-27 |
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| Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors. | 2005-01-03 |
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| Tetrahydroisoquinoline derivatives as melatonin MT2 receptor antagonists. | 2004-12-06 |
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| Inhibition of rodent brain monoamine oxidase and tyrosine hydroxylase by endogenous compounds - 1,2,3,4-tetrahydro-isoquinoline alkaloids. | 2004-11-02 |
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| Alkaloidal constituents of Mucuna pruriens seeds. | 2004-09 |
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| New substituted piperazines as ligands for melanocortin receptors. Correlation to the X-ray structure of "THIQ". | 2004-08-26 |
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| Solid-phase synthesis of 1,2,3,4-tetrahydroisoquinoline derivatives employing support-bound tyrosine esters in the Pictet-Spengler reaction. | 2004-07-13 |
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| Solid-phase synthesis of 1-substituted tetrahydroisoquinoline derivatives employing BOC-protected tetrahydroisoquinoline carboxylic acids. | 2004-07-13 |
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| Stereoselective synthesis of atropisomeric korupensamines A and B utilizing planar chiral arene chromium complex. | 2004-06-11 |
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| Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoquinolizidine alkaloid by using a domino process. | 2004-06-07 |
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| Pivotal role of an endogenous tetrahydroisoquinoline, salsolinol, in stress- and suckling-induced release of prolactin. | 2004-06 |
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| Effect of 1,2,3,4,-tetrahydroisoquinoline administration under conditions of CYP2D inhibition on dopamine metabolism, level of tyrosine hydroxylase protein and the binding of [3H]GBR 12,935 to dopamine transporter in the rat nigrostriatal, dopaminergic system. | 2004-05-29 |
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| Structure of hydrated clusters of tetrahydroisoquinoline [THIQ-(H2O)(n=1,3)] investigated by jet spectroscopy. | 2004-05-22 |
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| Potential roles of NF-kappaB and ERK1/2 in cytoprotection against oxidative cell death induced by tetrahydropapaveroline. | 2004-05-01 |
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| Carbazates as potent inhibitors of hormone-sensitive lipase. | 2004-04-05 |
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| Development of novel 1,2,3,4-tetrahydroisoquinoline derivatives and closely related compounds as potent and selective dopamine D3 receptor ligands. | 2004-04-02 |
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| In vivo bioconversion of tetrahydroisoquinoline by recombinant coclaurine N-methyltransferase. | 2004-04 |
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| Comparison of four modulators of drug metabolism as protectants against the hepatotoxicity of the novel antitumor drug yondelis (ET-743) in the female rat and in hepatocytes in vitro. | 2004-04 |
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| Ruthenium-catalyzed anti-Markovnikov hydroamination of vinylarenes. | 2004-03-10 |
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| Disposition of 1,2,3,4,-tetrahydroisoquinoline in the brain of male Wistar and Dark Agouti rats. | 2004-01-23 |
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| Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors. | 2004-01-05 |
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| Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives. | 2004-01 |
|
| A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction. | 2004 |
|
| In vitro interaction between ecteinascidin 743 (ET-743) and radiation, in relation to its cell cycle effects. | 2003-12-15 |
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| Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle. | 2003-12-07 |
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| Possible role of interleukin-6 in PC12 cell death induced by MPP+ and tetrahydroisoquinoline. | 2003-12 |
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| Structural specificity for the inhibitory effect of calmodulin on specific 125I-omega-conotoxin GVIA binding. | 2003-12 |
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| Intermolecular, markovnikov hydroamination of vinylarenes with alkylamines. | 2003-11-26 |
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| The Pictet-Spengler reaction in solid-phase combinatorial chemistry. | 2003-11 |
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| The interaction of tetrahydroisoquinoline derivatives with antinociceptive action of morphine and oxotremorine in mice. | 2003-11 |
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| Specific nonpeptide inhibitors of puromycin-sensitive aminopeptidase with a 2,4(1H,3H)-quinazolinedione skeleton. | 2003-11 |
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| Synthesis and pharmacological evaluation of 1-oxo-2-(3-piperidyl)-1,2,3,4- tetrahydroisoquinolines and related analogues as a new class of specific bradycardic agents possessing I(f) channel inhibitory activity. | 2003-10-23 |
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| Organolathanide-catalyzed regioselective intermolecular hydroamination of alkenes, alkynes, vinylarenes, di- and trivinylarenes, and methylenecyclopropanes. Scope and mechanistic comparison to intramolecular cyclohydroaminations. | 2003-10-15 |
|
| Debenzylation of tertiary amines using phosgene or triphosgene: an efficient and rapid procedure for the preparation of carbamoyl chlorides and unsymmetrical ureas. Application in carbon-11 chemistry. | 2003-09-19 |
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| Presence of reticuline in rat brain: a pathway for morphine biosynthesis. | 2003-09-10 |
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| Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). | 2003-08-27 |
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| Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp.. | 2003-08 |
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| Influence of acute and chronic 1,2,3,4-tetrahydroisoquinoline administration on the expression of proenkephalin mRNA in the rat striatum. | 2003-07-29 |
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| Endogenous risk factors in Parkinson's disease: dopamine and tetrahydroisoquinolines. | 2003-07-18 |
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| Estrogen receptor modulators: identification and structure-activity relationships of potent ERalpha-selective tetrahydroisoquinoline ligands. | 2003-07-03 |
|
| Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-alpha converting enzyme (TACE). | 2003-06-16 |
|
| New strategy for the synthesis of tetrahydroisoquinoline alkaloids. | 2003-06-12 |
|
| New scaffolds in the development of mu opioid-receptor ligands. | 2003-05-05 |
|
| Synthesis and pharmacological study of Rho-kinase inhibitors: pharmacomodulations on the lead compound Fasudil. | 2003-04 |
|
| The potent anticancer compound ecteinascidin-743 (ET-743) as its 2-propanol disolvate. | 2003-04 |
|
| A study of the influence of newly synthesized acyclonucleosides and 1,2,3,4-tetrahydroisoquinoline derivatives on deoxythymidine and deoxycytidine kinase activities in human neurofibrosarcoma and ovarian cancer. | 2003 |
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| A possible physiological role for cerebral tetrahydroisoquinolines. | 2003 |
|
| Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids. | 2002-03-01 |
|
| Advances in the chemistry and pharmacology of ecteinascidins, a promising new class of anti-cancer agents. | 2001-11 |
Patents
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| Code System | Code | Type | Description | ||
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202-050-0
Created by
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DTXSID6026115
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7046
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TETRAHYDROISOQUINOLINE
Created by
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15312
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91-21-4
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56W89FBX3E
Created by
admin on Mon Mar 31 17:36:11 GMT 2025 , Edited by admin on Mon Mar 31 17:36:11 GMT 2025
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SUBSTANCE RECORD
