Norsalsolinol

Last updated
Norsalsolinol
Norsalsolinol.svg
Norsalsolinol molecule spacefill.png
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
PubChem CID
UNII
  • InChI=1S/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2 X mark.svgN
    Key: MBFUSGLXKQWVDW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2
    Key: MBFUSGLXKQWVDW-UHFFFAOYAF
  • C1CNCC2=CC(=C(C=C21)O)O
Properties
C9H11NO2
Molar mass 165.189 g/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Neurotoxin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Norsalsolinol is a tetrahydroisoquinoline that is produced naturally in the body through the 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]

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. [10]

See also

References

  1. ↑ Maruyama W, Takahashi T, Minami M, Takahashi A, Dostert P, Nagatsu T, Naoi M (1993). "Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines". Advances in Neurology. 60: 224–30. PMID   8093579.
  2. ↑ Maruyama Y, Suzuki Y, Kazusaka A, Fujita S (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. 63 (5): 493–7. doi: 10.1292/jvms.63.493 . PMID   11411492.
  3. ↑ Maruyama Y, Suzuki Y, Kazusaka A, Fujita S (June 2001). "Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter". Archives of Toxicology. 75 (4): 209–13. Bibcode:2001ArTox..75..209M. doi:10.1007/s002040000202. PMID   11482518. S2CID   38150947.
  4. ↑ Kobayashi H, Fukuhara K, Tada-Oikawa S, Yada Y, Hiraku Y, Murata M, Oikawa S (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. 108 (2): 397–407. doi:10.1111/j.1471-4159.2008.05774.x. PMID   19012744.
  5. ↑ Dostert P, Strolin Benedetti M, Della Vedova F, Allievi C, La Croix R, Dordain G, Vernay D, Durif F (1993). "Dopamine-derived tetrahydroisoquinolines and Parkinson's disease". Advances in Neurology. 60: 218–23. PMID   8420138.
  6. ↑ Musshoff F, Daldrup T, Bonte W, Leitner A, Lesch OM (October 1997). "Salsolinol and norsalsolinol in human urine samples". Pharmacology Biochemistry and Behavior. 58 (2): 545–50. doi:10.1016/S0091-3057(97)00251-7. PMID   9300617. S2CID   76761.
  7. ↑ Musshoff F, Lachenmeier DW, Kroener L, Schmidt P, Dettmeyer R, Madea B (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). 49 (5): 837–49. PMID   14528920.
  8. ↑ Scholz J, Klingemann I, Moser A (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. 75 (4): 634–6. doi:10.1136/jnnp.2003.010769. PMC   1739023 . PMID   15026514.
  9. ↑ Musshoff F, Lachenmeier DW, Schmidt P, Dettmeyer R, Madea B (January 2005). "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. 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". www.pubfacts.com. Retrieved 2017-10-02.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.