# Solasodine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Solasodine
> Markdown URL: https://mediated.wiki/source/Solasodine.md
> Source: https://en.wikipedia.org/wiki/Solasodine
> Source revision: 1274130428
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477858890
| ImageFile = Solasodine.svg
| IUPACName = (22''R'',25''R'')-Spirosol-5α-en-3β-ol
| SystematicName = (2''S'',2′''R'',4a''R'',4b''S'',5′''R'',6a''S'',6b''R'',7''S'',9a''S'',10a''S'',10b''S'')-4a,5′,6a,7-Tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naptho[2′,1′:4,5]indeno[2,1-''b'']furan-8,2′-piperidin]-2-ol
| OtherNames = Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S
|Section1={{Chembox Identifiers
| Abbreviations = 
| CASNo = 126-17-0
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L40Y453Y96
| EINECS = 204-774-2
| PubChem = 442985
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 391288
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 514596
| SMILES = O[C@@H]6C/C5=C/C[C@@H]1[C@H](CC[C@]3([C@H]1C[C@@H]4O[C@@]2(NC[C@H](C)CC2)[C@H]([C@H]34)C)C)[C@@]5(C)CC6
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KWVISVAMQJWJSZ-VKROHFNGSA-N
| RTECS =
| MeSHName = 
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 9190
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C10822
}}
|Section2={{Chembox Properties
| C=27 | H=43 | N=1 | O=2
| Appearance =
| Density = 
| MeltingPt = 
| MeltingPt_notes =
| BoilingPt = 
| BoilingPt_notes = 
| Solubility = 
| SolubleOther = 
| Solvent = 
| pKa = 
| pKb = 
  }}
|Section7={{Chembox Hazards
| ExternalSDS = 
| MainHazards = 
| NFPA-H = 
| NFPA-F = 
| NFPA-R = 
| NFPA-S =
| HPhrases = 
| PPhrases = 
| GHS_ref  = 
| FlashPt = 
| AutoignitionPt = 
| ExploLimits = 
| PEL = 
  }}
}}

'''Solasodine''' is a [poisonous](/source/poisonous) [alkaloid](/source/alkaloid) [chemical compound](/source/chemical_compound) that occurs in plants of the family [Solanaceae](/source/Solanaceae) such as potatoes and tomatoes.<ref name=Everist>{{cite book |last=Everist |first=S.L. |title=Poisonous Plants of Australia |publisher=Angus & Robertson |year=1981 |isbn=978-0-207-14228-4}}</ref> [Solasonine](/source/Solasonine) and [solamargine](/source/solamargine) are [glycoalkaloid](/source/glycoalkaloid) derivatives of solasodine.<ref name=Everist/> Solasodine is [teratogenic](/source/teratogenic) to hamster fetuses in a dose of 1200 to 1600&nbsp;mg/kg.<ref>{{cite book |last=Kinghorn |first=A.D. |chapter=Toxins and Teratogens of the Solanaceae and Liliaceae |title=Toxic plants |publisher=Society for Economic Botany, Columbia University Press |year=2010 |pages=75–76 |isbn=978-0231515689 |chapter-url=https://books.google.com/books?id=CZPDzu2dGDEC&pg=PA75}}</ref>
A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.<ref>{{cite journal |title=Medicinal significance, pharmacological activities, and analytical aspects of solasodine: A concise report of current scientific literature |first=Kanika |last=Patel |first2=Ravi B.|last2=Singh |first3=Dinesh K.|last3=Patel |journal=Journal of Acute Disease |volume=2 |issue=2 |year=2013 |pages=92–98 |doi=10.1016/S2221-6189(13)60106-7 |doi-access=free }}</ref>

== Uses ==
It is commercially used as a precursor for the production of complex [steroidal](/source/steroidal) compounds such as [contraceptive pill](/source/contraceptive_pill)s, via a [16-DPA](/source/16-DPA) intermediate.<ref name=Everist/>

== See also ==
* ''[Solanum mauritianum](/source/Solanum_mauritianum)''

== References ==
{{reflist}}

Category:Steroidal alkaloids
Category:Plant toxins
Category:Steroidal alkaloids found in Solanaceae
Category:Spiro compounds

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Adapted from the Wikipedia article [Solasodine](https://en.wikipedia.org/wiki/Solasodine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Solasodine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.