Scoulerine

Scoulerine
	Scoulerine
Names
	IUPAC name 3,10-Dimethoxyberbine-2,9-diol
	Systematic IUPAC name (13aS)-3,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol
	Other names (S)-Scoulerin; Discretamine; Aequaline
Identifiers
CAS Number	6451-73-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17129 ;
ChEMBL	ChEMBL1235966 ;
ChemSpider	388725 ;
KEGG	C02106 ;
PubChem CID	439654;
	InChI InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1 Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N ;
	SMILES Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4;
Properties
Chemical formula	C19H21NO4
Molar mass	327.380 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

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine.^[1] It is found in many plants, including opium poppy,^[2] Croton flavens,^[3] and certain plants in the genus Erythrina.^[4]

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Studies show that scoulerine is an antagonist in vitro at the α₂-adrenoceptor, α_1D-adrenoceptor and 5-HT receptor.^[5]^[6] It has also been found to be a GABA_A receptor agonist in vitro.^[3]^[7]

Biosynthesis