Pericine

Pericine
Names
IUPAC name
(1R,16E)-16-Ethylidene-2-methylene-4,14-diazatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9-tetraene
Other names
Subincanadine E
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C19H22N2/c1-3-14-12-21-10-8-15(14)13(2)19-17(9-11-21)16-6-4-5-7-18(16)20-19/h3-7,15,20H,2,8-12H2,1H3/b14-3-/t15-/m0/s1
    Key: VAUGOKMDSLQYNG-WNDJQJCJSA-N
  • C/C=C\1/CN2CCc3c4ccccc4[nH]c3C(=C)[C@@H]1CC2
Properties
C19H22N2
Molar mass 278.399 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pericine is one of a number of indole alkaloids found in the tree Picralima nitida, commonly known as akuamma. As with some other alkaloids from this plant such as akuammine, pericine has been shown to bind to mu opioid receptors in vitro, and has an IC50 of 0.6 μmol, within the range of a weak analgesic.[1] It may also have convulsant effects.[2]

Pericine has been prepared in the laboratory by total synthesis.[3][4]

  1. ^ Arens H, Borbe HO, Ulbrich B, Stöckigt J (December 1982). "Detection of pericine, a new CNS-active indole alkaloid from Picralima nitida cell suspension culture by opiate receptor binding studies". Planta Medica. 46 (4): 210–4. doi:10.1055/s-2007-971216. PMID 6298847. S2CID 7758884.
  2. ^ Roberts MF, Wink M (30 June 1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Springer. pp. 68–69. ISBN 978-0-306-45465-3.
  3. ^ Tian J, Du Q, Guo R, Li Y, Cheng B, Zhai H (June 2014). "Total synthesis of indole alkaloid (±)-subincanadine E". Organic Letters. 16 (12): 3173–5. doi:10.1021/ol501308p. PMID 24869784.
  4. ^ Kalshetti MG, Argade NP (October 2017). "Total Synthesis of (±)/(+)-Subincanadine E and Determination of Absolute Configuration". The Journal of Organic Chemistry. 82 (20): 11126–11133. doi:10.1021/acs.joc.7b02122. PMID 28952728.