Scoulerine

Scoulerine

Names
IUPAC names (13aS)-3,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino [3,2-a]isoquinoline-2,9-diol
Other names Discretamine, Aequaline, Scoulerin.
Identifiers
CAS Number	605-34-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17129
ChEMBL	ChEMBL1235966
ChemSpider	388725
PubChem	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 InChI=1/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-HNNXBMFYBO
SMILES Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4
Properties
Chemical formula	C19H21NO4
Molar mass	327.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid that derives from reticuline and is a precursor of berberine. It is found in many plants, including Opium poppy,^[1] Croton flavens,^[2] and certain plants in the Erythrina genus.^[3]

Studies show that scoulerine is an antagonist in vitro at the α₂-adrenoceptor, α_1D-adrenoceptor and 5-HT receptor.^[4][5] It has also been found to be a GABA_A receptor agonist in vitro.^[2][6]

References

1. Frick S; Chitty JA; Kramell R; Schmidt J; Allen RS; Larkin PJ; Kutchan TM. (2004). "Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots.". Transgenic Res. 13 (6): 607–13. doi:10.1007/s11248-004-2892-6. PMID 15672841.
2. Eisenreich WJ; Hofner G; Bracher F. (2003). "Alkaloids from Croton flavens L. and their affinities to GABA-receptors.". Nat Prod Res. 17 (6): 437–40. doi:10.1080/1478641031000111516. PMID 14577695.
3. Ito K. (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–56. PMID 10375996.
4. Ko FN; Yu SM; Su MJ; Wu YC; Teng CM. (1993). "Pharmacological activity of (−)-discretamine, a novel vascular alpha-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens.". Br J Pharmacol. 110 (2): 882–8. doi:10.1111/j.1476-5381.1993.tb13895.x. PMC 2175899. PMID 7902181.
5. Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM. (1994). "(−)-Discretamine, a selective alpha 1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens.". Br J Pharmacol. 112 (4): 1174–80. doi:10.1111/j.1476-5381.1994.tb13207.x. PMC 1910235. PMID 7952879.
6. Halbsguth C; Meissner O; Haberlein H. (2003). "Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site.". Planta Med. 69 (4): 305–9. doi:10.1055/s-2003-38869. PMID 12709895.