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Revision as of 19:42, 10 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation← Previous edit Latest revision as of 02:15, 16 September 2024 edit undoCitation bot (talk | contribs)Bots5,391,854 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Monoaminergic neurotoxins | #UCB_Category 15/47 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 424782505
| Watchedfields = changed
| ImageFile = Norsalsolinol.png
| verifiedrevid = 449585406
| ImageFile = Norsalsolinol.svg
| ImageSize = 200px | ImageSize = 200px
| ImageAlt = Skeletal formula of norsalsolinol
| IUPACName = 1,2,3,4-tetrahydroisoquinoline-6,7-diol
| ImageFile1 = Norsalsolinol molecule spacefill.png
| 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 | OtherNames = 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 34827-33-3 | CASNo = 34827-33-3
| CASNo_Ref = {{cascite}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9SPO03ZH41
| PubChem = 36937 | PubChem = 36937
| SMILES = C1CNCC2=CC(=C(C=C21)O)O | SMILES = C1CNCC2=CC(=C(C=C21)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| 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 = {{stdinchicite|changed|chemspider}}
| 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 = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MBFUSGLXKQWVDW-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
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}} }}


'''Norsalsolinol''' is a chemical compound which is produced naturally in the body through ] of ].<ref name="pmid8093579">{{cite journal |author=Maruyama W, Takahashi T, Minami M, Takahashi A, Dostert P, Nagatsu T, Naoi M |title=Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines |journal=Advances in Neurology |volume=60 |issue= |pages=224–30 |year=1993 |pmid=8093579 |doi= |url=}}</ref> It has been shown to be a selective dopaminergic ],<ref name="pmid11411492">{{cite journal |author=Maruyama Y, Suzuki Y, Kazusaka A, Fujita S |title=Norsalsolinol uptake into secretory vesicles via vesicular monoamine transporter and its secretion by membrane depolarization or purinoceptor stimulation in PC12 cells |journal=The Journal of Veterinary Medical Science / the Japanese Society of Veterinary Science |volume=63 |issue=5 |pages=493–7 |year=2001 |month=May |pmid=11411492 |doi= |url=}}</ref><ref name="pmid11482518">{{cite journal |author=Maruyama Y, Suzuki Y, Kazusaka A, Fujita S |title=Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter |journal=Archives of Toxicology |volume=75 |issue=4 |pages=209–13 |year=2001 |month=June |pmid=11482518 |doi= 10.1007/s002040000202|url=}}</ref><ref name="pmid19012744">{{cite journal |author=Kobayashi H, Fukuhara K, Tada-Oikawa S, Yada Y, Hiraku Y, Murata M, Oikawa S |title=The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease |journal=Journal of Neurochemistry |volume=108 |issue=2 |pages=397–407 |year=2009 |month=January |pmid=19012744 |doi=10.1111/j.1471-4159.2008.05774.x |url=}}</ref> and has been suggested as a possible cause of neurodegenerative conditions such as ] and the brain damage associated with ],<ref name="pmid8420138">{{cite journal |author=Dostert P, Strolin Benedetti M, Della Vedova F, Allievi C, La Croix R, Dordain G, Vernay D, Durif F |title=Dopamine-derived tetrahydroisoquinolines and Parkinson's disease |journal=Advances in Neurology |volume=60 |issue= |pages=218–23 |year=1993 |pmid=8420138 |doi= |url=}}</ref><ref name="pmid9300617">{{cite journal |author=Musshoff F, Daldrup T, Bonte W, Leitner A, Lesch OM |title=Salsolinol and norsalsolinol in human urine samples |journal=Pharmacology, Biochemistry, and Behavior |volume=58 |issue=2 |pages=545–50 |year=1997 |month=October |pmid=9300617 |doi= 10.1016/S0091-3057(97)00251-7|url=}}</ref> although evidence for a causal relationship is unclear.<ref name="pmid14528920">{{cite journal |author=Musshoff F, Lachenmeier DW, Kroener L, Schmidt P, Dettmeyer R, Madea B |title=Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective |journal=Cellular and Molecular Biology (Noisy-le-Grand, France) |volume=49 |issue=5 |pages=837–49 |year=2003 |month=July |pmid=14528920 |doi= |url=}}</ref><ref name="pmid15026514">{{cite journal |author=Scholz J, Klingemann I, Moser A |title=Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease |journal=Journal of Neurology, Neurosurgery, and Psychiatry |volume=75 |issue=4 |pages=634–6 |year=2004 |month=April |pmid=15026514 |pmc=1739023 |doi= 10.1136/jnnp.2003.010769|url=}}</ref><ref name="pmid15654290">{{cite journal |author=Musshoff F, Lachenmeier DW, Schmidt P, Dettmeyer R, Madea B |title=Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics |journal=Alcoholism, Clinical and Experimental Research |volume=29 |issue=1 |pages=46–52 |year=2005 |month=January |pmid=15654290 |doi= 10.1097/01.ALC.0000150011.81102.C2|url=}}</ref> '''Norsalsolinol''' is a chemical compound that is produced naturally in the body through the ] of ].<ref name="pmid8093579">{{cite journal |vauthors=Maruyama W, Takahashi T, Minami M, Takahashi A, Dostert P, Nagatsu T, Naoi M |title=Cytotoxicity of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines |journal=Advances in Neurology |volume=60 |pages=224–30 |year=1993 |pmid=8093579 }}</ref> It has been shown to be a selective dopaminergic ],<ref name="pmid11411492">{{cite journal |vauthors=Maruyama Y, Suzuki Y, Kazusaka A, Fujita S |title=Norsalsolinol uptake into secretory vesicles via vesicular monoamine transporter and its secretion by membrane depolarization or purinoceptor stimulation in PC12 cells |journal=The Journal of Veterinary Medical Science |volume=63 |issue=5 |pages=493–7 |date=May 2001 |pmid=11411492 |doi= 10.1292/jvms.63.493|doi-access=free }}</ref><ref name="pmid11482518">{{cite journal |vauthors=Maruyama Y, Suzuki Y, Kazusaka A, Fujita S |title=Uptake of the dopaminergic neurotoxin, norsalsolinol, into PC12 cells via dopamine transporter |journal=Archives of Toxicology |volume=75 |issue=4 |pages=209–13 |date=June 2001 |pmid=11482518 |doi= 10.1007/s002040000202|bibcode=2001ArTox..75..209M |s2cid=38150947 }}</ref><ref name="pmid19012744">{{cite journal |vauthors=Kobayashi H, Fukuhara K, Tada-Oikawa S, Yada Y, Hiraku Y, Murata M, Oikawa S |title=The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease |journal=Journal of Neurochemistry |volume=108 |issue=2 |pages=397–407 |date=January 2009 |pmid=19012744 |doi=10.1111/j.1471-4159.2008.05774.x |doi-access= }}</ref> and has been suggested as a possible cause of neurodegenerative conditions such as ] and the brain damage associated with ],<ref name="pmid8420138">{{cite journal |vauthors=Dostert P, Strolin Benedetti M, Della Vedova F, Allievi C, La Croix R, Dordain G, Vernay D, Durif F |title=Dopamine-derived tetrahydroisoquinolines and Parkinson's disease |journal=Advances in Neurology |volume=60 |pages=218–23 |year=1993 |pmid=8420138 }}</ref><ref name="pmid9300617">{{cite journal |vauthors=Musshoff F, Daldrup T, Bonte W, Leitner A, Lesch OM |title=Salsolinol and norsalsolinol in human urine samples |journal=Pharmacology Biochemistry and Behavior |volume=58 |issue=2 |pages=545–50 |date=October 1997 |pmid=9300617 |doi= 10.1016/S0091-3057(97)00251-7|s2cid=76761 }}</ref> although evidence for a causal relationship is unclear.<ref name="pmid14528920">{{cite journal |vauthors=Musshoff F, Lachenmeier DW, Kroener L, Schmidt P, Dettmeyer R, Madea B |title=Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective |journal=Cellular and Molecular Biology (Noisy-le-Grand, France) |volume=49 |issue=5 |pages=837–49 |date=July 2003 |pmid=14528920 }}</ref><ref name="pmid15026514">{{cite journal |vauthors=Scholz J, Klingemann I, Moser A |title=Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease |journal=Journal of Neurology, Neurosurgery, and Psychiatry |volume=75 |issue=4 |pages=634–6 |date=April 2004 |pmid=15026514 |pmc=1739023 |doi= 10.1136/jnnp.2003.010769}}</ref><ref name="pmid15654290">{{cite journal |vauthors=Musshoff F, Lachenmeier DW, Schmidt P, Dettmeyer R, Madea B |title=Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics |journal=Alcoholism: Clinical and Experimental Research |volume=29 |issue=1 |pages=46–52 |date=January 2005 |pmid=15654290 |doi= 10.1097/01.ALC.0000150011.81102.C2}}</ref>

(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<ref>{{Cite web|url=https://www.pubfacts.com/detail/26032572/R-Salsolinol-a-product-of-ethanol-metabolism-stereospecifically-induces-behavioral-sensitization-and|title=(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake. {{!}} PubFacts.com|website=www.pubfacts.com|access-date=2017-10-02}}</ref>


== See also == == See also ==
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{{Reflist|2}} {{Reflist|2}}


{{Monoamine neurotoxins}}


]
{{Neurotoxins}}
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{{Dopaminergics}}
]




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