Phytochemicals/Scoulerine

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, α1D-adrenoceptor and 5-HT receptor.[4][5] It has also been found to be a GABAA receptor agonist.[2][6]

Scoulerine
Identifiers
CAS number 605-34-5 checkY
PubChem 439654
ChemSpider 388725 checkY
ChEBI CHEBI:17129 checkY
ChEMBL CHEMBL1235966 checkY
Jmol-3D images Image 1
{{#if:Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4|{{Collapsible list|title = | 1 =

Oc1c4c(ccc1OC)C[C@H]3c2c(cc(OC)c(O)c2)CCN3C4

  • 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 checkY
    Key: KNWVMRVOBAFFMH-HNNXBMFYSA-N checkY


    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

Properties
Molecular formula C19H21NO4
Molar mass 327.37 g/mol
 ☒N (verify) (what is: checkY/☒N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

References

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  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. 2.0 2.1 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. PMID 7902181. PMC 2175899. //www.ncbi.nlm.nih.gov/pmc/articles/PMC2175899/. 
  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. PMID 7952879. PMC 1910235. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1910235/. 
  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. 
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