From Wikipedia, the free encyclopedia
(−)-Stepholidine
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Names
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IUPAC name
3,9-Dimethoxyberbine-2,10-diol
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Systematic IUPAC name
(13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol
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Other names
l-Stepholidine
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Identifiers
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ChEMBL
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ChemSpider
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MeSH
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Stepholidine
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UNII
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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 NKey: JKPISQIIWUONPB-HNNXBMFYSA-N NInChI=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
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COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
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Properties
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C19H21NO4
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Molar mass
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327.374 g/mol
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
(−)-Stepholidine is a proto
berberine
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
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^ 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.
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^ 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.
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^ 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.
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^ 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.