Stepholidine

(−)-Stepholidine
Names
	IUPAC name 3,9-Dimethoxyberbine-2,10-diol
	Systematic IUPAC name (13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolinoisoquinoline-2,10-diol
	Other names l-Stepholidine
Identifiers
CAS Number	16562-13-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL487387 ;
ChemSpider	5293188 ;
MeSH	Stepholidine
PubChem CID	6917970;
UNII	0UPX3E69W8 ;
CompTox Dashboard (EPA)	DTXSID70937112 ;
	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 Key: JKPISQIIWUONPB-HNNXBMFYSA-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=C23CC4=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 , 100 kPa). verify (what is ?) 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]

References

^ 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.
^ 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.
^ 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.
^ 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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[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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See also

References