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Stepholidine

From Wikipedia, the free encyclopedia
(−)-Stepholidine
Names
IUPAC name
3,9-Dimethoxyberbine-2,10-diol
Systematic IUPAC name
(13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol
Other names
l-Stepholidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSHStepholidine
UNII
  • InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1 ☒N
    Key: JKPISQIIWUONPB-HNNXBMFYSA-N ☒N
  • InChI=1/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
    Key: JKPISQIIWUONPB-HNNXBMFYBD
  • COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
Properties
C19H21NO4
Molar mass327.374 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

(−)-Stepholidine is a protoberberinealkaloid found in the plantStephania intermedia.

Stepholidine activity includes dualD2 receptorantagonist andD1 receptoragonist, and has shownantipsychotic activity in animal studies.[1][2][3][4]

See also

[edit]

References

[edit]
  1. ^Natesan S, Reckless GE, Barlow KB, et al. (August 2008). "The antipsychotic potential of l-stepholidine-a naturally occurring dopamine receptor D(1) agonist and D (2) antagonist".Psychopharmacology.199 (2):275–89.doi:10.1007/s00213-008-1172-1.PMID 18521575.S2CID 21653956.
  2. ^Mo J, Guo Y, Yang YS, Shen JS, Jin GZ, Zhen X (2007)."Recent developments in studies of l-stepholidine and its analogs: chemistry, pharmacology and clinical implications".Curr. Med. Chem.14 (28):2996–3002.doi:10.2174/092986707782794050.PMID 18220736. Archived from the original on July 20, 2012.
  3. ^Jin GZ, Zhu ZT, Fu Y (January 2002). "(-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions".Trends Pharmacol. Sci.23 (1):4–7.doi:10.1016/S0165-6147(00)01929-5.PMID 11804640.
  4. ^Fu W, Shen J, Luo X, et al. (September 2007)."Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: molecular modeling and dynamics simulations".Biophys. J.93 (5):1431–41.doi:10.1529/biophysj.106.088500.PMC 1948031.PMID 17468175.
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists


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