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
| Molecular Formula | C11H15NO2 |
| Molecular Weight | 193.2423 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|
| Inhibitory effects of endogenous dopaminergic neurotoxin, norsalsolinol on dopamine secretion in PC12 rat pheochromocytoma cells. | 2001 Jun |
|
| Norsalsolinol uptake into secretory vesicles via vesicular monoamine transporter and its secretion by membrane depolarization or purinoceptor stimulation in PC12 cells. | 2001 May |
|
| 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 |
|
| Tetrahydroisoquinoline derivatives of enkephalins: synthesis and properties. | 2002 May 15 |
|
| Cell death in Parkinson's disease. | 2002 Sep |
|
| Dopamine-derived endogenous N-methyl-(R)-salsolinol: its role in Parkinson's disease. | 2002 Sep-Oct |
|
| Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective. | 2003 Jul |
|
| Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). | 2003 Jul-Aug |
|
| N-methyl-norsalsolinol modulates serotonin metabolism in the rat caudate nucleus: correlation with behavioural changes. | 2003 Mar |
|
| [Asymmetric reactions based on activation and structure control of molecule--asymmetric reaction of lithiated nucleophiles]. | 2004 Feb |
|
| Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. | 2004 Mar |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 21:30:43 GMT 2023
by
admin
on
Fri Dec 15 21:30:43 GMT 2023
|
| Record UNII |
9Q83ETU10C
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
101467-40-7
Created by
admin on Fri Dec 15 21:30:43 GMT 2023 , Edited by admin on Fri Dec 15 21:30:43 GMT 2023
|
PRIMARY | |||
|
m9748
Created by
admin on Fri Dec 15 21:30:43 GMT 2023 , Edited by admin on Fri Dec 15 21:30:43 GMT 2023
|
PRIMARY | Merck Index | ||
|
40010
Created by
admin on Fri Dec 15 21:30:43 GMT 2023 , Edited by admin on Fri Dec 15 21:30:43 GMT 2023
|
PRIMARY | |||
|
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
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
