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{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 368933896
| verifiedrevid = 368933896
|Name=(−)-Stepholidine
| Name=(−)-Stepholidine
|ImageFile=(−)-Stepholidine.svg
| ImageFile=(−)-Stepholidine.svg
|ImageSize=
| ImageSize=
|IUPACName=(13a''S'')-3,9-dimethoxy-5,8,13,13''a''-tetrahydro-6''H''-isoquino[3,2-''a'']isoquinoline-2,10-diol
| IUPACName=3,9-Dimethoxyberbine-2,10-diol
| SystematicName=(13a''S'')-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6''H''-isoquinolino[3,2-''a'']isoquinoline-2,10-diol
|OtherNames=''l''-Stepholidine
| OtherNames=''l''-Stepholidine
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=16562-13-3
| CASNo=16562-13-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem=5290
| UNII = 0UPX3E69W8
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 487387
| ChEMBL = 487387
⚫
| PubChem = 6917970
⚫
| SMILES=COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫
| MeSHName=Stepholidine
| ChemSpiderID = 5293188
⚫
| SMILES = COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
| 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
| InChIKey = JKPISQIIWUONPB-HNNXBMFYBD
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JKPISQIIWUONPB-HNNXBMFYSA-N
⚫
| MeSHName=Stepholidine
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>19</sub>H<sub>21</sub>NO<sub>4</sub>
| Formula=C<sub>19</sub>H<sub>21</sub>NO<sub>4</sub>
| MolarMass=327.374 g/mol
| MolarMass=327.374 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}
'''(−)-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 |author=Natesan S, Reckless GE, Barlow KB, ''et al.'' |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 |year=2008 |month=August |pmid=18521575 |doi=10.1007/s00213-008-1172-1 |url=}}</ref><ref>{{cite journal |author=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 |author=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 |year=2002 |month=January |pmid=11804640 |doi= 10.1016/S0165-6147(00)01929-5|url=http://linkinghub.elsevier.com/retrieve/pii/S0165614700019295}}</ref><ref>{{cite journal |author=Fu W, Shen J, Luo X, ''et al.'' |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 |year=2007 |month=September |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 |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>


==See also==
==See also==
{{cmn|colwidth=30em|
*[[Apomorphine]]
*[[Apomorphine]]
*[[Bulbocapnine]]
*[[Bulbocapnine]]
Line 41: Line 55:
*[[Pukateine]]
*[[Pukateine]]
*[[Tetrahydropalmatine]]
*[[Tetrahydropalmatine]]
}}


==References==
==References==
{{Reflist}}
{{Reflist}}


{{Dopamine receptor modulators}}
{{Dopaminergics}}


[[Category:D1-receptor agonists]]
[[Category:D1-receptor agonists]]
[[Category:D2 antagonists]]
[[Category:D2 antagonists]]
[[Category:Alkaloids]]
[[Category:Benzylisoquinoline alkaloids]]
[[Category:Phenols]]
[[Category:Phenols]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]

Revision as of 04:37, 7 May 2023

(−)-Stepholidine
Names
IUPAC name
3,9-Dimethoxyberbine-2,10-diol
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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Stepholidine
UNII
  • 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
  • COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
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).
☒N verify (what is checkY☒N ?)

(−)-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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