Affinisine

Affinisine
Names
	IUPAC name 1-Methylsarpagan-17-ol
	Systematic IUPAC name [(6S,9E,10R,11R,12S)-9-Ethylidene-5-methyl-5,6,7,8,9,10,11,11a,12-decahydro-6,10-methanoindolo[2,3-g]quinolizin-11-yl]methanol
	Other names De(hydroxymethyl)voachalotinol
Identifiers
CAS Number	2912-11-0;
3D model (JSmol)	Interactive image;
ChemSpider	10172574;
PubChem CID	12000107;
UNII	J96TYR7CHG ;
CompTox Dashboard (EPA)	DTXSID201045726 ;
	InChI InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3-/t14-,16+,18-,19-/m0/s1 Key: UVWQYWHKTZABSO-ILADVTTDSA-N; InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3-/t14-,16+,18-,19-/m0/s1 Key: UVWQYWHKTZABSO-ILADVTTDSA-N;
	SMILES CN1C2=C(C=CC=C2)C3=C1[C@@](C[C@@]4([H])/C(C5)=C\C)([H])[N@]5[C@@]([C@@]([H])4CO)([H])C3;
Properties
Chemical formula	C20H24N2O
Molar mass	308.425 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana.^[1]^[2] Structurally, it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.^[3]^[4]

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Pharmacology