Stepholidine

(−)-Stepholidine
Names
IUPAC name
3,9-Dimethoxyberbine-2,10-diol
Preferred 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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Stepholidine
PubChem CID
UNII
InChI
  • 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
SMILES
  • COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
Properties
Chemical formula
 C19H21NO4
Molar mass 327.374 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

(−)-Stepholidine is a protoberberine alkaloid found in the plant Stephania intermedia.

Stepholidine activity includes dual D2 receptor antagonist and D1 receptor agonist, and has shown antipsychotic activity in animal studies.[1][2][3][4]

See also

References

  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.
  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.


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