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	4747-99-3  Y
3D model (JSmol)	Interactive image
Beilstein Reference	313061
ChEBI	CHEBI:28770
ChEMBL	ChEMBL19068
ChemSpider	17491
ECHA InfoCard	100.158.898
EC Number	630-581-1
KEGG	C06350
PubChem CID	18519
UNII	V1EWJ6B8KY  Y
CompTox Dashboard (EPA)	DTXSID70963850
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
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetrahydropapaveroline, also known as norlaudanosoline, is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloids. ^[1]

Brain biochemistry

Tetrahydropapaveroline is relevant to brain pathologies. ^[2]

It can be formed in trace amounts in the brain by a condensation reaction of dopamine and dopaldehyde (a metabolite of dopamine). ^{[2] [3]}

It inhibits dopamine uptake within the cerebral cortex. ^[4]

References

1. Hawkins, Kristy M.; Smolke, Christina D. (2008). "Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae". Nature Chemical Biology. 4 (9): 564–573. doi:10.1038/nchembio.105. PMC   2830865 . PMID   18690217.
2. Richter, Derek (14 October 2016). Addiction and Brain Damage. Routledge. p. 24. ISBN   978-1-315-45403-0.
3. 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.
4. 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.