Stepholidine: Difference between revisions

(−)-Stepholidine
Names
	IUPAC name (13aS)-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-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;
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=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). verify (what is ?) Infobox references

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Revision as of 19:01, 17 September 2016

(−)-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 (Berl.). 199 (2): 275–89. doi:10.1007/s00213-008-1172-1. PMID 18521575.
^ 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 (Berl.). 199 (2): 275–89. doi:10.1007/s00213-008-1172-1. PMID 18521575.

[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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+'''(−)-Stepholidine''' is a proto[[berberine]] [[alkaloid]] found in the plant ''[[Stephania|Stephania intermedia]]''.
-'''(−)-Stepholidine''' is a naturally occurring chemical compound found in the herb ''[[Stephania|Stephania intermedia]]''. Stepholidine is a dual [[dopamine receptor D2|D<sub>2</sub> receptor]] [[dopamine antagonist|antagonist]] and [[dopamine receptor D1|D<sub>1</sub> receptor]] [[agonist]], and has shown [[antipsychotic]] activity in animal studies.<ref>{{cite journal  |vauthors=Natesan S, Reckless GE, Barlow KB, etal |title=The antipsychotic potential of l-stepholidine-a naturally occurring dopamine receptor D(1) agonist and D (2) antagonist |journal=Psychopharmacology (Berl.) |volume=199 |issue=2 |pages=275–89 |date=August 2008 |pmid=18521575 |doi=10.1007/s00213-008-1172-1 |url=}}</ref><ref>{{cite journal |vauthors=Mo J, Guo Y, Yang YS, Shen JS, Jin GZ, Zhen X |title=Recent developments in studies of l-stepholidine and its analogs: chemistry, pharmacology and clinical implications |journal=Curr. Med. Chem. |volume=14 |issue=28 |pages=2996–3002 |year=2007 |pmid=18220736 |doi= 10.2174/092986707782794050|url=http://www.bentham-direct.org/pages/content.php?CMC/2007/00000014/00000028/0007C.SGM}}</ref><ref>{{cite journal |vauthors=Jin GZ, Zhu ZT, Fu Y |title=(-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions |journal=Trends Pharmacol. Sci. |volume=23 |issue=1 |pages=4–7 |date=January 2002 |pmid=11804640 |doi= 10.1016/S0165-6147(00)01929-5|url=http://linkinghub.elsevier.com/retrieve/pii/S0165614700019295}}</ref><ref>{{cite journal  |vauthors=Fu W, Shen J, Luo X, etal |title=Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: molecular modeling and dynamics simulations |journal=Biophys. J. |volume=93 |issue=5 |pages=1431–41 |date=September 2007 |pmid=17468175 |doi=10.1529/biophysj.106.088500 |url= |pmc=1948031}}</ref>
+Stepholidine activity includes dual [[dopamine receptor D2|D<sub>2</sub> receptor]] [[dopamine antagonist|antagonist]] and [[dopamine receptor D1|D<sub>1</sub> receptor]] [[agonist]], and has shown [[antipsychotic]] activity in animal studies.<ref>{{cite journal  |vauthors=Natesan S, Reckless GE, Barlow KB, etal |title=The antipsychotic potential of l-stepholidine-a naturally occurring dopamine receptor D(1) agonist and D (2) antagonist |journal=Psychopharmacology (Berl.) |volume=199 |issue=2 |pages=275–89 |date=August 2008 |pmid=18521575 |doi=10.1007/s00213-008-1172-1 |url=}}</ref><ref>{{cite journal |vauthors=Mo J, Guo Y, Yang YS, Shen JS, Jin GZ, Zhen X |title=Recent developments in studies of l-stepholidine and its analogs: chemistry, pharmacology and clinical implications |journal=Curr. Med. Chem. |volume=14 |issue=28 |pages=2996–3002 |year=2007 |pmid=18220736 |doi= 10.2174/092986707782794050|url=http://www.bentham-direct.org/pages/content.php?CMC/2007/00000014/00000028/0007C.SGM}}</ref><ref>{{cite journal |vauthors=Jin GZ, Zhu ZT, Fu Y |title=(-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions |journal=Trends Pharmacol. Sci. |volume=23 |issue=1 |pages=4–7 |date=January 2002 |pmid=11804640 |doi= 10.1016/S0165-6147(00)01929-5|url=http://linkinghub.elsevier.com/retrieve/pii/S0165614700019295}}</ref><ref>{{cite journal  |vauthors=Fu W, Shen J, Luo X, etal |title=Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: molecular modeling and dynamics simulations |journal=Biophys. J. |volume=93 |issue=5 |pages=1431–41 |date=September 2007 |pmid=17468175 |doi=10.1529/biophysj.106.088500 |url= |pmc=1948031}}</ref>
 ==See also==