Affinine

Affinine
Names
	IUPAC name (2S,6R,14S,E)-5-ethylidene-14-(hydroxymethyl)-3,14-dimethyl-2,3,4,5,6,7-hexahydro-1H-2,6-methanoazecino[5,4-b]indol-8(9H)-one
	Other names 17-hydroxy-vobasan-3-one,
Identifiers
CAS Number	2134-82-9;
3D model (JSmol)	Interactive image;
ChemSpider	4444714;
PubChem CID	5281345;
CompTox Dashboard (EPA)	DTXSID70415107 ;
	InChI InChI=1S/C21H26N2O2/c1-4-13-11-23(3)19-9-15-14-7-5-6-8-17(14)22-20(15)18(25)10-16(13)21(19,2)12-24/h4-8,16,19,22,24H,9-12H2,1-3H3/b13-4-/t16-,19+,21+/m1/s1 Key: PROSDVOTXQJUDA-PGVNYQEXSA-N;
	SMILES C/C=C1CN(C)[C@H]2CC3=C(C(C[C@H]/1[C@]2(C)CO)=O)NC4=C3C=CC=C4;
Properties
Chemical formula	C20H24N2O2
Molar mass	324.424 g·mol−1
Melting point	265°C (decomp.)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Affinine 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 vobasine alkaloid family and may be synthesized from tryptophan.^[3] Limited pharmacological testing has indicated that it may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase.^[4]

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