:Stepholidine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 368933896

| Name=(−)-Stepholidine

| ImageFile=(−)-Stepholidine.svg

| ImageClass = skin-invert-image

| ImageSize=

| IUPACName=3,9-Dimethoxyberbine-2,10-diol

| SystematicName=(13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol

| OtherNames=l-Stepholidine

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=16562-13-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0UPX3E69W8

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 487387

| PubChem = 6917970

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| 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

| Formula=C₁₉H₂₁NO₄

| MolarMass=327.374 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

(−)-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.{{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 }}{{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|archive-url=https://archive.today/20120720124648/http://www.bentham-direct.org/pages/content.php?CMC/2007/00000014/00000028/0007C.SGM|url-status=usurped|archive-date=July 20, 2012}}{{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}}{{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}}