Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H15NO2 |
| Molecular Weight | 193.2423 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(CCN[C@@H]2C)C=C1O
InChI
InChIKey=YTPRLBGPGZHUPD-SSDOTTSWSA-N
InChI=1S/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m1/s1
Salsoline is a metabolite of dopamine and is highly prevalent in the urine and cerebrospinal fluid of alcoholics at the time of intoxication and for several days after. Salsoline and related compounds bind to the Type A Mono-amine Oxidase inducing neuronal cell death. At one time salsoline was thought to be a biomarker for Parkinson's disease. However, it was later shown that treatment regimes result in an increased endogenous concentration of salsoline and related compounds.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Transfection-enforced Bcl-2 overexpression and an anti-Parkinson drug, rasagiline, prevent nuclear accumulation of glyceraldehyde-3-phosphate dehydrogenase induced by an endogenous dopaminergic neurotoxin, N-methyl(R)salsolinol. | 2001 Aug |
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| [Pathogenesis of idiopathic Parkinson's disease]. | 2001 Jul |
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| Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter. | 2001 Jun |
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| Norsalsolinol uptake into secretory vesicles via vesicular monoamine transporter and its secretion by membrane depolarization or purinoceptor stimulation in PC12 cells. | 2001 May |
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| Future of neuroprotection in Parkinson's disease. | 2001 Oct |
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| Mitochondrial permeability transition mediates apoptosis induced by N-methyl(R)salsolinol, an endogenous neurotoxin, and is inhibited by Bcl-2 and rasagiline, N-propargyl-1(R)-aminoindan. | 2002 Aug |
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| Mitochondria determine the survival and death in apoptosis by an endogenous neurotoxin, N-methyl(R)salsolinol, and neuroprotection by propargylamines. | 2002 May |
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| Tetrahydroisoquinoline derivatives of enkephalins: synthesis and properties. | 2002 May 15 |
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| Cell death in Parkinson's disease. | 2002 Sep |
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| Dopamine-derived endogenous N-methyl-(R)-salsolinol: its role in Parkinson's disease. | 2002 Sep-Oct |
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| Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective. | 2003 Jul |
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| Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). | 2003 Jul-Aug |
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| N-methyl-norsalsolinol modulates serotonin metabolism in the rat caudate nucleus: correlation with behavioural changes. | 2003 Mar |
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| Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease. | 2004 Apr |
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| [Studies on the alkaloids from Salsola collina Pall]. | 2004 Aug |
|
| Neuroprotective function of R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, [R-(-)-BPAP], against apoptosis induced by N-methyl(R)salsolinol, an endogenous dopaminergic neurotoxin, in human dopaminergic neuroblastoma SH-SY5Y cells. | 2004 May 21 |
|
| Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics. | 2005 Jan |
|
| Involvement of type A monoamine oxidase in neurodegeneration: regulation of mitochondrial signaling leading to cell death or neuroprotection. | 2006 |
|
| Type A monoamine oxidase is the target of an endogenous dopaminergic neurotoxin, N-methyl(R)salsolinol, leading to apoptosis in SH-SY5Y cells. | 2006 Jan |
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| N-Propargylamine protects SH-SY5Y cells from apoptosis induced by an endogenous neurotoxin, N-methyl(R)salsolinol, through stabilization of mitochondrial membrane and induction of anti-apoptotic Bcl-2. | 2006 Jan |
|
| A new alkaloid from Salsola collina. | 2007 Jun |
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| Role of acetaldehyde in tobacco smoke addiction. | 2007 Oct |
|
| Localization of N-methyl-norsalsolinol within rodent and human brain. | 2008 Aug 15 |
|
| Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection. | 2008 Dec |
|
| Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy. | 2008 Jan |
|
| Iron contributes to the formation of catechol isoquinolines and oxidative toxicity induced by overdose dopamine in dopaminergic SH-SY5Y cells. | 2008 Jun |
|
| A new microdialysis-electrochemical device for in vivo simultaneous determination of acetylcholine and choline in rat brain treated with N-methyl-(R)-salsolinol. | 2009 Aug 15 |
|
| The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease. | 2009 Jan |
|
| Additive protective effects of donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells. | 2009 Oct |
|
| Determination of salsolinol, norsalsolinol, and twenty-one biogenic amines using micellar electrokinetic capillary chromatography-electrochemical detection. | 2010 Jun |
|
| Catechol-O-methyltransferase: potential relationship to idiopathic hypertension. | 2010 Jun 30 |
Patents
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101467-40-7
Created by
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m9748
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admin on Fri Dec 15 21:30:43 GMT 2023 , Edited by admin on Fri Dec 15 21:30:43 GMT 2023
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40010
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9Q83ETU10C
Created by
admin on Fri Dec 15 21:30:43 GMT 2023 , Edited by admin on Fri Dec 15 21:30:43 GMT 2023
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ACTIVE MOIETY
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)
