Scoulerine

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Scoulerine
Scoulerine
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]
SMILES COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
Properties
Molecular formula C19H21NO4
Molar mass 327.37 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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[6][2].

[edit] 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. ^ 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): 437–40. 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. 
  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. 
  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. 

[edit] External links

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