Affinisine

{{Chembox

| ImageFile = Affinisine.svg

| ImageSize = 250px

| ImageAlt =

| IUPACName = 1-Methylsarpagan-17-ol

| SystematicName = [(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

| OtherNames = De(hydroxymethyl)voachalotinol

|Section1={{Chembox Identifiers

| CASNo = 2912-11-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J96TYR7CHG

| PubChem = 12000107

| ChemSpiderID = 10172574

| 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

| 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

| InChIKey = UVWQYWHKTZABSO-ILADVTTDSA-N

| StdInChI = 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

| StdInChIKey = UVWQYWHKTZABSO-ILADVTTDSA-N

}}

|Section2={{Chembox Properties

| C=20 | H=24 | N=2 | O=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

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Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana.{{cite journal|last1=Andrade|first1=Marcelo T.|last2=Lima|first2=Josélia A.|last3=Pinto|first3=Angelo C.|last4=Rezende|first4=Claudia M.|last5=Carvalho|first5=Meriane P.|last6=Epifanio|first6=Rosângela A.|title=Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme|journal=Bioorganic & Medicinal Chemistry|date=June 2005|volume=13|issue=12|pages=4092–4095|doi=10.1016/j.bmc.2005.03.045|pmid=15911323}}{{cite journal|last1=Clivio|first1=Pascale|last2=Richard|first2=Bernard|last3=Deverre|first3=Jean-Robert|last4=Sevenet|first4=Thierry|last5=Zeches|first5=Monique|last6=Le Men-Oliver|first6=Louisette|title=Alkaloids from leaves and root bark ofErvatamia hirta|journal=Phytochemistry|date=January 1991|volume=30|issue=11|pages=3785–3792|doi=10.1016/0031-9422(91)80111-D}} Structurally, it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.{{cite journal|last1=Liu|first1=Xiaoxiang|last2=Wang|first2=Tao|last3=Xu|first3=Qingge|last4=Ma|first4=Chunrong|last5=Cook|first5=James M|title=Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine|journal=Tetrahedron Letters|date=August 2000|volume=41|issue=33|pages=6299–6303|doi=10.1016/S0040-4039(00)01061-3}}{{cite journal|last1=Liao|first1=Xuebin|last2=Zhou|first2=Hao|last3=Yu|first3=Jianming|last4=Cook|first4=James M.|title=An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (−)-Talcarpine and (−)-Anhydromacrosalhine−methine|journal=The Journal of Organic Chemistry|date=November 2006|volume=71|issue=23|pages=8884–8890|doi=10.1021/jo061652u|pmid=17081019}}