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Affinine

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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
3D model (JSmol)
ChemSpider
  • 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
  • C/C=C1CN(C)[C@H]2CC3=C(C(C[C@H]/1[C@]2(C)CO)=O)NC4=C3C=CC=C4
Properties
C20H24N2O2
Molar mass 324.424 g·mol−1
Melting point 265°C (decomp.)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

See also

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References

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  1. ^ a b Weisbach, Jerry A.; Raffauf, Robert F.; Ribeiro, Oscar; Macko, Edward; Douglas, Bryce (April 1963). "Problems in chemotaxonomy I. Alkaloids ofPeschiera affinis". Journal of Pharmaceutical Sciences. 52 (4): 350–353. doi:10.1002/jps.2600520408. PMID 13999677.
  2. ^ Monnerat, Cecilia Silva; Souza, Jucimar Jorgeane de; Mathias, Leda; Braz-Filho, Raimundo; Vieira, Ivo José C. (November 2005). "A new indole alkaloid isolated from Tabernaemontana hystrix steud (Apocynaceae)". Journal of the Brazilian Chemical Society. 16 (6b): 1331–1335. doi:10.1590/S0103-50532005000800004.
  3. ^ Yang, Jie; Rallapalli, Sundari K.; Cook, James M. (February 2010). "The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine and 16-epiaffinine, as well as vobasinediol and 16-epivobasinediol". Tetrahedron Letters. 51 (5): 815–817. doi:10.1016/j.tetlet.2009.12.002.
  4. ^ Vieira, IJ; Medeiros, WL; Monnerat, CS; Souza, JJ; Mathias, L; Braz-Filho, R; Pinto, AC; Sousa, PM; Rezende, CM; Epifanio Rde, A (September 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures". Anais da Academia Brasileira de Ciências. 80 (3): 419–26. doi:10.1590/S0001-37652008000300003. PMID 18797794.


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