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
ChEBI	CHEBI:17129
ChEMBL	ChEMBL1235966
ChemSpider	388725
Jmol interactive 3D	Image
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 an alkaloid found in the Opium poppy,^[1] Croton flavens,^[2] and certain plants in the Erythrina genus.^[3] Studies show that scoulerine is an antagonist 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.^[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.

External links