Chemistry:Norsalsolinol

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Norsalsolinol
Skeletal formula of norsalsolinol
Space-filling model of the norsalsolinol molecule
Names
Preferred IUPAC name
1,2,3,4-Tetrahydroisoquinoline-6,7-diol
Other names
6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C9H11NO2
Molar mass 165.189 g/mol
Hazards
Main hazards Neurotoxin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Norsalsolinol is a chemical compound that is produced naturally in the body through metabolism of dopamine.[1] It has been shown to be a selective dopaminergic neurotoxin,[2][3][4] and has been suggested as a possible cause of neurodegenerative conditions such as Parkinson's disease and the brain damage associated with alcoholism,[5][6] although evidence for a causal relationship is unclear.[7][8][9]

(R)-Salsolinol which has been shown to be a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake in rats[10]

See also

References

  1. "Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines". Advances in Neurology 60: 224–30. 1993. PMID 8093579. 
  2. "Norsalsolinol uptake into secretory vesicles via vesicular monoamine transporter and its secretion by membrane depolarization or purinoceptor stimulation in PC12 cells". The Journal of Veterinary Medical Science 63 (5): 493–7. May 2001. doi:10.1292/jvms.63.493. PMID 11411492. 
  3. "Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter". Archives of Toxicology 75 (4): 209–13. June 2001. doi:10.1007/s002040000202. PMID 11482518. 
  4. "The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease". Journal of Neurochemistry 108 (2): 397–407. January 2009. doi:10.1111/j.1471-4159.2008.05774.x. PMID 19012744. 
  5. "Dopamine-derived tetrahydroisoquinolines and Parkinson's disease". Advances in Neurology 60: 218–23. 1993. PMID 8420138. 
  6. "Salsolinol and norsalsolinol in human urine samples". Pharmacology Biochemistry and Behavior 58 (2): 545–50. October 1997. doi:10.1016/S0091-3057(97)00251-7. PMID 9300617. 
  7. "Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective". Cellular and Molecular Biology (Noisy-le-Grand, France) 49 (5): 837–49. July 2003. PMID 14528920. 
  8. "Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease". Journal of Neurology, Neurosurgery, and Psychiatry 75 (4): 634–6. April 2004. doi:10.1136/jnnp.2003.010769. PMID 15026514. 
  9. "Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics". Alcoholism: Clinical and Experimental Research 29 (1): 46–52. January 2005. doi:10.1097/01.ALC.0000150011.81102.C2. PMID 15654290. 
  10. "(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake. | PubFacts.com". https://www.pubfacts.com/detail/26032572/R-Salsolinol-a-product-of-ethanol-metabolism-stereospecifically-induces-behavioral-sensitization-and.