Norsalsolinol

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title: "Norsalsolinol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["catechols", "human-pathological-metabolites", "monoaminergic-neurotoxins", "tetrahydroisoquinolines"] topic_path: "philosophy" source: "https://en.wikipedia.org/wiki/Norsalsolinol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449585406 | ImageFile = Norsalsolinol.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt = Skeletal formula of norsalsolinol | ImageFile1 = Norsalsolinol molecule spacefill.png | ImageClass1 = bg-transparent | ImageSize1 = 170 | ImageAlt1 = Space-filling model of the norsalsolinol molecule | PIN = 1,2,3,4-Tetrahydroisoquinoline-6,7-diol | OtherNames = 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline | Section1 = {{Chembox Identifiers | CASNo_Ref = | CASNo = 34827-33-3 | UNII_Ref = | UNII = 9SPO03ZH41 | PubChem = 36937 | SMILES = C1CNCC2=CC(=C(C=C21)O)O | ChemSpiderID_Ref = | ChemSpiderID = 33891 | ChEBI = 173739 | InChI = 1/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2 | InChIKey = MBFUSGLXKQWVDW-UHFFFAOYAF | StdInChI_Ref = | StdInChI = 1S/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2 | StdInChIKey_Ref = | StdInChIKey = MBFUSGLXKQWVDW-UHFFFAOYSA-N | Section2 = {{Chembox Properties | Formula = C9H11NO2 | MolarMass = 165.189 g/mol | Section3 = {{Chembox Hazards | MainHazards = Neurotoxin

Norsalsolinol is a tetrahydroisoquinoline that is produced naturally in the body through the metabolism of dopamine. It has been shown to be a selective dopaminergic neurotoxin, and has been suggested as a possible cause of neurodegenerative conditions such as Parkinson's disease and the brain damage associated with alcoholism, although evidence for a causal relationship is unclear.

The related compound (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.

References

References

  1. (1993). "Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines". Advances in Neurology.
  2. (May 2001). "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.
  3. (June 2001). "Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter". Archives of Toxicology.
  4. (January 2009). "The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease". Journal of Neurochemistry.
  5. (1993). "Dopamine-derived tetrahydroisoquinolines and Parkinson's disease". Advances in Neurology.
  6. (October 1997). "Salsolinol and norsalsolinol in human urine samples". Pharmacology Biochemistry and Behavior.
  7. (July 2003). "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).
  8. (April 2004). "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.
  9. (January 2005). "Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics". Alcoholism: Clinical and Experimental Research.
  10. "(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake. {{!}} PubFacts.com".

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catecholshuman-pathological-metabolitesmonoaminergic-neurotoxinstetrahydroisoquinolines