Scoulerine

Scoulerine
Names
	IUPAC name (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 (JSmol)	Interactive image;
ChEBI	CHEBI:17129 ;
ChEMBL	ChEMBL1235966 ;
ChemSpider	388725 ;
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 ; 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). verify (what is ?) 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

^ 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): 607–613. doi:10.1007/s11248-004-2892-6. PMID 15672841.
^ ^a ^b Eisenreich WJ; Hofner G; Bracher F (2003). "Alkaloids from Croton flavens L. and their affinities to GABA-receptors". Nat Prod Res. 17 (6): 437–440. doi:10.1080/1478641031000111516. PMID 14577695.
^ Ito K (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–356. PMID 10375996.
^ Ko FN; Yu SM; Su MJ; Wu YC; Teng CM (1993). "Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 110 (2): 882–888. doi:10.1111/j.1476-5381.1993.tb13895.x. PMC 2175899. PMID 7902181.
^ Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM (1994). "(−)-Discretamine, a selective α_1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 112 (4): 1174–1180. doi:10.1111/j.1476-5381.1994.tb13207.x. PMC 1910235. PMID 7952879.
^ 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): 305–309. doi:10.1055/s-2003-38869. PMID 12709895.

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[transformation-Frick-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): 607–613. doi:10.1007/s11248-004-2892-6. PMID 15672841.

[alkaloids-from-croton-Eisenreich-2] Eisenreich WJ; Hofner G; Bracher F (2003). "Alkaloids from Croton flavens L. and their affinities to GABA-receptors". Nat Prod Res. 17 (6): 437–440. doi:10.1080/1478641031000111516. PMID 14577695.

[studies-on-the-alkaloids-Ito-3] Ito K (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi. 119 (5): 340–356. PMID 10375996.

[pharmacological-activity-Ko-4] Ko FN; Yu SM; Su MJ; Wu YC; Teng CM (1993). "Pharmacological activity of (−)-discretamine, a novel vascular α-adrenoceptor and 5-hydroxytryptamine receptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 110 (2): 882–888. doi:10.1111/j.1476-5381.1993.tb13895.x. PMC 2175899. PMID 7902181.

[discretamine-Ko-5] Ko FN; Guh JH; Yu SM; Hou YS; Wu YC; Teng CM (1994). "(−)-Discretamine, a selective α_1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens". Br J Pharmacol. 112 (4): 1174–1180. doi:10.1111/j.1476-5381.1994.tb13207.x. PMC 1910235. PMID 7952879.

[positive-Halbsguth-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): 305–309. doi:10.1055/s-2003-38869. PMID 12709895.

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