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
605-34-5 
ChEBI CHEBI:17129 Yes
ChEMBL ChEMBL1235966 
ChemSpider 388725 Yes
Jmol-3D images Image
PubChem 439654
Properties
C19H21NO4
Molar mass 327.37 g/mol
Except where noted otherwise, data is 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, α1D-adrenoceptor and 5-HT receptor.[4][5] It has also been found to be a GABAA 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): 60713. 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): 43740. doi:10.1080/1478641031000111516. PMID 14577695.
  3. Ito K. (1999). "Studies on the alkaloids of Erythrina plants". Yakugaku Zasshi 119 (5): 34056. 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): 8828. 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): 117480. 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): 3059. doi:10.1055/s-2003-38869. PMID 12709895.

External links