Norsalsolinol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 449585406

| ImageFile = Norsalsolinol.svg

| ImageSize = 200px

| ImageAlt = Skeletal formula of norsalsolinol

| 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

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 34827-33-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9SPO03ZH41

| PubChem = 36937

| 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

| Formula = C₉H₁₁NO₂

| MolarMass = 165.189 g/mol

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| Section3 = {{Chembox Hazards

| MainHazards = Neurotoxin

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

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.{{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}}