Solasodine

Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes.^[1] Solasonine and solamargine are glycoalkaloid derivatives of solasodine.^[1] Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg.^[2] 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.^[3]

Solasodine

Names
IUPAC name (22R,25R)-Spirosol-5α-en-3β-ol
Systematic IUPAC name (2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-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
Other names Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S
Identifiers
CAS Number	126-17-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9190 N
ChEMBL	ChEMBL514596 N
ChemSpider	391288 Y
ECHA InfoCard	100.004.341
EC Number	204-774-2
KEGG	C10822 N
PubChem CID	442985
UNII	L40Y453Y96 Y
CompTox Dashboard (EPA)	DTXSID101030558
InChI InChI=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 Y Key: KWVISVAMQJWJSZ-VKROHFNGSA-N Y
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
Properties
Chemical formula	C27H43NO2
Molar mass	413.646 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Uses

It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate.^[1]

See also

• Solanum mauritianum