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=CC=CC=C2CN1
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 |
|---|---|---|
| Effects of single and repeated administration of 1,2,3,4-tetrahydroisoquinoline analogs on the binding of [11C]raclopride to dopamine D2 receptors in the mouse brain. | 2001 |
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| Opposite effect of simple tetrahydroisoquinolines on amphetamine- and morphine-stimulated locomotor activity in mice. | 2001 |
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| Effects of a 3-alkyl-, 4-hydroxy- and/or 8-aromatic-substituent on the phenylethanolamine N-methyltransferase inhibitor potency and alpha2-adrenoceptor affinity of 2,3,4,5-tetrahydro-1H-2-benzazepines. | 2001 Aug |
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| Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties. | 2001 Jul |
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| An unusual decarboxylative Maillard reaction between L-DOPA and D-glucose under biomimetic conditions: factors governing competition with Pictet-Spengler condensation. | 2001 Jul 27 |
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| Oxidative DNA damage and cytotoxicity induced by copper-stimulated redox cycling of salsolinol, a neurotoxic tetrahydroisoquinoline alkaloid. | 2001 Jun 15 |
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| Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. | 2001 Nov |
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| Total syntheses of conformationally constrained didemnin B analogues. replacements of N,O-dimethyltyrosine with L-1,2,3,4-tetrahydroisoquinoline and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline. | 2001 Nov 16 |
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| Stress-related polyketide metabolism of Dioncophyllaceae and Ancistrocladaceae. | 2001 Oct |
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| Parallel synthesis and biological activity of a new class of high affinity and selective delta-opioid ligand. | 2001 Oct |
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| Active conformation of some arylpiperazine postsynaptic 5-HT(1A) receptor antagonists. | 2002 Apr |
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| Two optically active isoquinoline derivatives. | 2002 Aug |
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| Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids. | 2002 Mar 1 |
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| Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson's disease: studies using heterologous expression systems of the dopamine transporter. | 2002 Mar 1 |
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| Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. | 2002 May |
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| Endogenous risk factors in Parkinson's disease: dopamine and tetrahydroisoquinolines. | 2002 Nov-Dec |
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| 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 |
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| Tetrahydroisoquinoline alkaloids and 2-deoxyribonolactones from Aristolochia arcuata. | 2003 Apr |
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| Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp. | 2003 Aug |
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| Possible role of interleukin-6 in PC12 cell death induced by MPP+ and tetrahydroisoquinoline. | 2003 Dec |
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| Estrogen receptor modulators: identification and structure-activity relationships of potent ERalpha-selective tetrahydroisoquinoline ligands. | 2003 Jul 3 |
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| Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). | 2003 Jul-Aug |
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| New strategy for the synthesis of tetrahydroisoquinoline alkaloids. | 2003 Jun 12 |
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| Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-alpha converting enzyme (TACE). | 2003 Jun 16 |
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| New scaffolds in the development of mu opioid-receptor ligands. | 2003 May 5 |
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| The Pictet-Spengler reaction in solid-phase combinatorial chemistry. | 2003 Nov |
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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 Nov-Dec |
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| A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction. | 2004 |
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| Carbazates as potent inhibitors of hormone-sensitive lipase. | 2004 Apr 5 |
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| Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives. | 2004 Jan |
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| Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors. | 2004 Jan 5 |
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| Ruthenium-catalyzed anti-Markovnikov hydroamination of vinylarenes. | 2004 Mar 10 |
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| Potential roles of NF-kappaB and ERK1/2 in cytoprotection against oxidative cell death induced by tetrahydropapaveroline. | 2004 May 1 |
Patents
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202-050-0
Created by
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DTXSID6026115
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7046
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TETRAHYDROISOQUINOLINE
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15312
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91-21-4
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56W89FBX3E
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SUBSTANCE RECORD
