Tetrahydropapaveroline

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

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

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.[3]

References

  1. 1 2 Richter, 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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