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19716-56-4 | Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-
CAS No: 19716-56-4 Catalog No: AG002AN7 MDL No:MFCD22741220
Product Description
Catalog Number:
AG002AN7
Chemical Name:
Isoquinoline, 1,2,3,4-tetrahydro-1-(phenylmethyl)-
CAS Number:
19716-56-4
Molecular Formula:
C16H17N
Molecular Weight:
223.3129
MDL Number:
MFCD22741220
IUPAC Name:
1-benzyl-1,2,3,4-tetrahydroisoquinoline
InChI:
InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2
InChI Key:
YRYCIFUZSUMAAY-UHFFFAOYSA-N
SMILES:
c1ccc(cc1)CC1NCCc2c1cccc2
NSC Number:
140739
Properties
Complexity:
232
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
223.136g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
223.319g/mol
Monoisotopic Mass:
223.136g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
12A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
3.3
Literature
| Title | Journal |
|---|---|
| Detection of a novel neurotoxic metabolite of Parkinson's disease-related neurotoxin, 1-benzyl-1,2,3,4- tetrahydroisoquinoline. | The Journal of toxicological sciences 20140101 |
| Both stereoselective (R)- and (S)-1-Methyl-1,2,3,4-tetrahydroisoquinoline enantiomers protect striatal terminals against rotenone-induced suppression of dopamine release. | Neurotoxicity research 20110801 |
| Novel 5, 6-Dihydropyrrolo[2,1-a]isoquinolines as Scaffolds for Synthesis of Lamellarin Analogues. | Evidence-based complementary and alternative medicine : eCAM 20110101 |
| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline binds with tubulin beta, a substrate of parkin, and reduces its polyubiquitination. | Journal of neurochemistry 20100901 |
| Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine. | Journal of natural products 20100827 |
| Recent N-atom containing compounds from indo-pacific invertebrates. | Marine drugs 20100101 |
| Structure-activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives. | European journal of medicinal chemistry 20091101 |
| Beta2-adrenoceptor-mediated tracheal relaxation induced by higenamine from Nandina domestica Thunberg. | Planta medica 20091001 |
| Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution. | International journal of molecular sciences 20090801 |
| Single administration of 1-benzyl-1,2,3,4-tetrahydroisoquinoline increases the extracellular concentration of dopamine in rat striatum. | Neuroscience 20090602 |
| (S)-reticuline induces vasorelaxation through the blockade of L-type Ca(2+) channels. | Naunyn-Schmiedeberg's archives of pharmacology 20090201 |
| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline, an endogenous parkinsonism-inducing toxin, strongly potentiates MAO-dependent dopamine oxidation and impairs dopamine release: ex vivo and in vivo neurochemical studies. | Neurotoxicity research 20090101 |
| Simultaneous analysis of 1,2,3,4-tetrahydroisoquinolines by high-performance liquid chromatography using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080501 |
| Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen. | Journal of ethnopharmacology 20060719 |
| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline passes through the blood-brain barrier of rat brain: an in vivo microdialysis study. | Neuroscience letters 20060227 |
| Capillary liquid chromatography-tandem mass spectrometry of tetrahydroisoquinoline derived neurotoxins: a study on the blood-brain barrier of rat brain. | Journal of chromatography. A 20060127 |
| Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors. | British journal of pharmacology 20050901 |
| Structural analyses of metabolites of phenolic 1-benzyltetrahydroisoquinolines in plant cell cultures by LC/NMR, LC/MS, and LC/CD. | Journal of natural products 20050701 |
| Neuroprotective effect of 1-methyl-1,2,3,4-tetrahydroisoquinoline on cultured rat mesencephalic neurons in the presence or absence of various neurotoxins. | Brain research 20050208 |
| The GC-MS detection and characterization of reticuline as a marker of opium use. | Forensic science international 20040528 |
| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline, a Parkinsonism-inducing endogenous toxin, increases alpha-synuclein expression and causes nuclear damage in human dopaminergic cells. | Journal of neuroscience research 20040515 |
| The GC-MS detection and characterization of reticuline as a marker of opium use. | Forensic science international 20040310 |
| API-ionspray MS and MS/MS study on the structural characterization of bisbenzylisoquinoline alkaloids. | Journal of pharmaceutical and biomedical analysis 20040127 |
| Electrospray tandem mass spectrometry for structural characterization of aporphine- benzylisoquinoline alkaloids. | European journal of mass spectrometry (Chichester, England) 20040101 |
| 1-Benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ), an endogenous neurotoxin, induces dopaminergic cell death through apoptosis. | Neurotoxicology 20030601 |
| No reduction of dopamine transporter binding sites in mice following treatment with the TIQ analogue 1-benzyl-1,2,3,4-tetrahydroisoquinoline. | Brain research 20030117 |
| Neurotoxicity of an endogenous brain amine, 1-benzyl-1,2,3,4-tetrahydroisoquinoline, in organotypic slice co-culture of mesencephalon and striatum. | Neuroscience 20030101 |
| Salsolinol causing parkinsonism activates endoplasmic reticulum-stress signaling pathways in human dopaminergic SK-N-SH cells. | Neuro-Signals 20030101 |
| [Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances]. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20021101 |
| The effects of higenamine on LPS-induced experimental disseminated intravascular coagulation (DIC) in rats. | Planta medica 20020401 |
| Antithrombotic effects of YS-49 and YS-51--1-naphthylmethyl analogs of higenamine. | Thrombosis research 20011115 |
| Anti-thrombotic effects of higenamine. | Planta medica 20011001 |
| Biochemical and pathological study of endogenous 1-benzyl-1,2,3,4-tetrahydroisoquinoline-induced parkinsonism in the mouse. | Brain research 20010713 |
| Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties. | Journal of neurochemistry 20010701 |
| Synthesis and preliminary pharmacological evaluation of 5-hydroxy- and 5,6-dihydroxy-1,2,3,7,12,12a-hexahydrobenzo[5,6]cyclohepta[1,2,3-ij]isoquinoline derivatives as dopamine receptor ligands. | Bioorganic & medicinal chemistry 20010601 |
| Diastereoselective synthesis of 1-benzyltetrahydroisoquinoline derivatives from amino acids via 1,4 chirality transfer. Part 1. | Organic letters 20010405 |
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