Stepholidine: Difference between revisions
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{{chembox |
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| verifiedrevid = 368933896 |
| verifiedrevid = 368933896 |
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|Name=(−)-Stepholidine |
| Name=(−)-Stepholidine |
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|ImageFile=(−)-Stepholidine.svg |
| ImageFile=(−)-Stepholidine.svg |
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|ImageSize= |
| ImageSize= |
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|IUPACName= |
| IUPACName=3,9-Dimethoxyberbine-2,10-diol |
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| SystematicName=(13a''S'')-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6''H''-isoquinolino[3,2-''a'']isoquinoline-2,10-diol |
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|OtherNames=''l''-Stepholidine |
| OtherNames=''l''-Stepholidine |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=16562-13-3 |
| CASNo=16562-13-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0UPX3E69W8 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 487387 |
| ChEMBL = 487387 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 5293188 |
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| 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 |
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| InChIKey = JKPISQIIWUONPB-HNNXBMFYBD |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JKPISQIIWUONPB-HNNXBMFYSA-N |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula=C<sub>19</sub>H<sub>21</sub>NO<sub>4</sub> |
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| MolarMass=327.374 g/mol |
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'''(−)-Stepholidine''' is a proto[[berberine]] [[alkaloid]] found in the plant ''[[Stephania|Stephania intermedia]]''. |
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⚫ | 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 |volume=199 |issue=2 |pages=275–89 |date=August 2008 |pmid=18521575 |doi=10.1007/s00213-008-1172-1 |s2cid=21653956 }}</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}}</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 |pmc=1948031}}</ref> |
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==See also== |
==See also== |
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{{cmn|colwidth=30em| |
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*[[Apomorphine]] |
*[[Apomorphine]] |
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*[[Bulbocapnine]] |
*[[Bulbocapnine]] |
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*[[Pukateine]] |
*[[Pukateine]] |
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*[[Tetrahydropalmatine]] |
*[[Tetrahydropalmatine]] |
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}} |
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==References== |
==References== |
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{{Reflist}} |
{{Reflist}} |
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{{Dopamine receptor modulators}} |
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{{Dopaminergics}} |
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[[Category:D1-receptor agonists]] |
[[Category:D1-receptor agonists]] |
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[[Category:D2 antagonists]] |
[[Category:D2 antagonists]] |
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[[Category: |
[[Category:Benzylisoquinoline alkaloids]] |
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[[Category:Phenols]] |
[[Category:Phenols]] |
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[[Category:Phenol ethers]] |
[[Category:Phenol ethers]] |
Revision as of 04:37, 7 May 2023
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 | |
Other names
l-Stepholidine
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
MeSH | Stepholidine |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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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(−)-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
- ^ 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.