tetrahydropapaveroline

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| ImageFile = Tetrahydropapaveroline.svg

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| IUPACName = 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

| OtherNames = Norlaudanosoline; Tetrahydroxypapaveroline

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| CASNo = 4747-99-3

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

| UNII = V1EWJ6B8KY

| PubChem = 18519

| SMILES = C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O

| InChI=1S/C16H17NO4/c18-13-2-1-9(6-14(13)19)5-12-11-8-16(21)15(20)7-10(11)3-4-17-12/h1-2,6-8,12,17-21H,3-5H2

| InChIKey = ABXZOXDTHTTZJW-UHFFFAOYSA-N

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| C=16|H=17|N=1|O=4

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Tetrahydropapaveroline (norlaudanosoline) is a benzyltetrahydroisoquinoline alkaloid.{{cite book|last1=Richter|first1=Derek|title=Addiction and Brain Damage|date=14 October 2016|publisher=Routledge|isbn=978-1-315-45403-0|page=24|url=https://books.google.com/books?id=6MNCDQAAQBAJ&pg=PT24|language=en}}

It can be formed in trace amounts in the brain by a condensation reaction of dopamine and dopaldehyde (a metabolite of dopamine).{{cite journal | title = Alcohol drinking: abnormal intake caused by tetrahydropapaveroline in brain |author=RD Myers |author2=CL Melchior | journal = Science | date = 29 April 1977 | volume = 196 | issue = 4289 | pages = 554–556 | doi = 10.1126/science.557839 | pmid = 557839 | bibcode = 1977Sci...196..554M }}

It inhibits dopamine uptake within the cerebral cortex.{{Cite journal |last=Okada |first=T. |last2=Shimada |first2=S. |last3=Sato |first3=K. |last4=Kotake |first4=Y. |last5=Kawai |first5=H. |last6=Ohta |first6=S. |last7=Tohyama |first7=M. |last8=Nishimura |first8=T. |date=January 1998 |title=Tetrahydropapaveroline and its derivatives inhibit dopamine uptake through dopamine transporter expressed in HEK293 cells |url=https://pubmed.ncbi.nlm.nih.gov/9572583/ |journal=Neuroscience Research |volume=30 |issue=1 |pages=87–90 |doi=10.1016/s0168-0102(97)00121-1 |issn=0168-0102 |pmid=9572583}}