affinine

{{Chembox

| ImageFile = Affinine.svg

| ImageSize = 150px

| ImageAlt =

| IUPACName = (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

| OtherNames = 17-hydroxy-vobasan-3-one,

|Section1={{Chembox Identifiers

| CASNo = 2134-82-9

| PubChem = 5281345

| SMILES = C/C=C1CN(C)[C@H]2CC3=C(C(C[C@H]/1[C@]2(C)CO)=O)NC4=C3C=CC=C4

| ChemSpiderID = 4444714

| 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

| InChIKey = PROSDVOTXQJUDA-PGVNYQEXSA-N

}}

|Section2={{Chembox Properties

| C=20 | H=24 | N=2 | O=2

| MolarMass =

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| Density =

| MeltingPt = 265°C (decomp.)

| MeltingPt_ref = {{cite journal|last1=Weisbach|first1=Jerry A.|last2=Raffauf|first2=Robert F.|last3=Ribeiro|first3=Oscar|last4=Macko|first4=Edward|last5=Douglas|first5=Bryce|title=Problems in chemotaxonomy I. Alkaloids ofPeschiera affinis|journal=Journal of Pharmaceutical Sciences|date=April 1963|volume=52|issue=4|pages=350–353|doi=10.1002/jps.2600520408|pmid=13999677|doi-access=free}}

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| Solubility = }}

|Section3={{Chembox Hazards

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| AutoignitionPt = }}

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Affinine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana.{{cite journal|last1=Monnerat|first1=Cecilia Silva|last2=Souza|first2=Jucimar Jorgeane de|last3=Mathias|first3=Leda|last4=Braz-Filho|first4=Raimundo|last5=Vieira|first5=Ivo José C.|title=A new indole alkaloid isolated from Tabernaemontana hystrix steud (Apocynaceae)|journal=Journal of the Brazilian Chemical Society|date=November 2005|volume=16|issue=6b|pages=1331–1335|doi=10.1590/S0103-50532005000800004|doi-access=free}} Structurally it can be considered a member of the vobasine alkaloid family and may be synthesized from tryptophan.{{cite journal|last1=Yang|first1=Jie|last2=Rallapalli|first2=Sundari K.|last3=Cook|first3=James M.|title=The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine and 16-epiaffinine, as well as vobasinediol and 16-epivobasinediol|journal=Tetrahedron Letters|date=February 2010|volume=51|issue=5|pages=815–817|doi=10.1016/j.tetlet.2009.12.002}} Limited pharmacological testing has indicated that it may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase.{{cite journal|last1=Vieira|first1=IJ|last2=Medeiros|first2=WL|last3=Monnerat|first3=CS|last4=Souza|first4=JJ|last5=Mathias|first5=L|last6=Braz-Filho|first6=R|last7=Pinto|first7=AC|last8=Sousa|first8=PM|last9=Rezende|first9=CM|last10=Epifanio Rde|first10=A|title=Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures.|journal=Anais da Academia Brasileira de Ciências|date=September 2008|volume=80|issue=3|pages=419–26|pmid=18797794|doi=10.1590/S0001-37652008000300003|doi-access=free}}