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Tetrahydropapaveroline

From Wikipedia, the free encyclopedia
Tetrahydropapaveroline
Names
IUPAC name
1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Other names
Norlaudanosoline; Tetrahydroxypapaveroline
Identifiers
3D model (JSmol)
ECHA InfoCard100.158.898Edit this at Wikidata
UNII
  • 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
  • C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC(=C(C=C3)O)O
Properties
C16H17NO4
Molar mass287.315 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Tetrahydropapaveroline (norlaudanosoline) is a benzyltetrahydroisoquinolinealkaloid.[1]

It can be formed in trace amounts in the brain by acondensation reaction ofdopamine anddopaldehyde (ametabolite of dopamine).[1][2]

It inhibits dopamine uptake within thecerebral cortex.[3]

References

[edit]
  1. ^abRichter, Derek (14 October 2016).Addiction and Brain Damage. Routledge. p. 24.ISBN 978-1-315-45403-0.
  2. ^RD Myers; CL Melchior (29 April 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.
  3. ^Okada, T.; Shimada, S.; Sato, K.; Kotake, Y.; Kawai, H.; Ohta, S.; Tohyama, M.; Nishimura, T. (January 1998)."Tetrahydropapaveroline and its derivatives inhibit dopamine uptake through dopamine transporter expressed in HEK293 cells".Neuroscience Research.30 (1):87–90.doi:10.1016/s0168-0102(97)00121-1.ISSN 0168-0102.PMID 9572583.
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