Tetrahydropapaveroline

Tetrahydropapaveroline (norlaudanosoline) is a benzyltetrahydroisoquinoline alkaloid.[1]

Tetrahydropapaveroline
Names
IUPAC name
1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Other names
Norlaudanosoline; Tetrahydroxypapaveroline
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.158.898
PubChem CID
UNII
InChI
  • 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
    Key: ABXZOXDTHTTZJW-UHFFFAOYSA-N
SMILES
  • C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O
Properties
Chemical formula
 C16H17NO4
Molar mass 287.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It can be formed in trace amounts in the brain by a condensation reaction of dopamine and dopaldehyde (a metabolite of dopamine).[1][2]

It inhibits dopamine uptake within the cerebral cortex.

References
  1. Richter, Derek (14 October 2016). Addiction and Brain Damage. Routledge. p. 24. ISBN 9781315454030.
  2. RD Myers, CL Melchior (29 Apr 1977). "Alcohol drinking: abnormal intake caused by tetrahydropapaveroline in brain". Science. 196 (4289): 554–556. Bibcode:1977Sci...196..554M. doi:10.1126/science.557839. PMID 557839.{{cite journal}}: CS1 maint: uses authors parameter (link)
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