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
CAS Number	84638-28-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	4944986;
PubChem CID	6440735;
UNII	56UJL0958V;
CompTox Dashboard (EPA)	DTXSID101018405 ;
	InChI 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;
	SMILES C/C=C\1/CN2CCc3c4ccccc4[nH]c3C(=C)[C@@H]1CC2;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ 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.
^ Roberts MF, Wink M (30 June 1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. pp. 68–69. ISBN 978-0-306-45465-3.
^ 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.
^ 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.

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