Norsalsolinol
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| Norsalsolinol | ||
|---|---|---|
 | ||
| IUPAC name 1,2,3,4-tetrahydroisoquinoline-6,7-diol | ||
| Other names 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline | ||
| Identifiers | ||
| CAS number | 34827-33-3  | |
| PubChem | 36937 | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C9H11NO2 | |
| Molar mass | 165.189 g/mol | |
| Hazards | ||
| Main hazards | Neurotoxin | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
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]
See also
References
- ↑ 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.
- ↑ 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 / the Japanese Society of Veterinary Science 63 (5): 493–7. PMID 11411492.
- ↑ 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. doi:10.1007/s002040000202. PMID 11482518.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
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