View source for Chemistry:Pericine

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| verifiedrevid = 450846495
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| ImageFile = Pericine.svg
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| IUPACName = (1''R'',16''E'')-16-Ethylidene-2-methylene-4,14-diazatetracyclo[12.2.2.0<sup>3,11</sup>.0<sup>5,10</sup>]octadeca-3(11),5,7,9-tetraene
| OtherNames = Subincanadine E 
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| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 84638-28-8
| PubChem = 6440735
| UNII = 56UJL0958V
| ChemSpiderID = 4944986
| SMILES = C/C=C\1/CN2CCc3c4ccccc4[nH]c3C(=C)[C@@H]1CC2
|  StdInChI = 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
|  StdInChIKey = VAUGOKMDSLQYNG-WNDJQJCJSA-N
  }}
| Section2 = {{Chembox Properties
| C=19 | H=22 | N=2 
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| Section3 = {{Chembox Hazards
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'''Pericine''' is one of a number of [[Chemistry:Indole|indole]] [[Chemistry:Alkaloid|alkaloid]]s found in the tree ''Picralima nitida'', commonly known as akuamma. As with some other alkaloids from this plant such as [[Chemistry:Akuammine|akuammine]], pericine has been shown to bind to mu opioid receptors ''[[In vitro|in vitro]]'', and has an IC<sub>50</sub> of 0.6&nbsp;μmol, within the range of a weak [[Biology:Analgesic|analgesic]].<ref>{{cite journal | vauthors = Arens H, Borbe HO, Ulbrich B, Stöckigt J | title = Detection of pericine, a new CNS-active indole alkaloid from Picralima nitida cell suspension culture by opiate receptor binding studies | journal = Planta Medica | volume = 46 | issue = 4 | pages = 210–4 | date = December 1982 | pmid = 6298847 | doi = 10.1055/s-2007-971216 | s2cid = 7758884 }}</ref> It may also have [[Chemistry:Convulsant|convulsant]] effects.<ref>{{cite book | vauthors = Roberts MF, Wink M | title = Alkaloids: Biochemistry, Ecology, and Medicinal Applications | date = 30 June 1998 | pages = 68–69 | publisher = Springer | isbn = 978-0-306-45465-3 }}</ref>

Pericine has been prepared in the laboratory by [[Chemistry:Total synthesis|total synthesis]].<ref>{{cite journal | vauthors = Tian J, Du Q, Guo R, Li Y, Cheng B, Zhai H | title = Total synthesis of indole alkaloid (±)-subincanadine E | journal = Organic Letters | volume = 16 | issue = 12 | pages = 3173–5 | date = June 2014 | pmid = 24869784 | doi = 10.1021/ol501308p }}</ref><ref>{{cite journal | vauthors = Kalshetti MG, Argade NP | title = Total Synthesis of (±)/(+)-Subincanadine E and Determination of Absolute Configuration | journal = The Journal of Organic Chemistry | volume = 82 | issue = 20 | pages = 11126–11133 | date = October 2017 | pmid = 28952728 | doi = 10.1021/acs.joc.7b02122 }}</ref>

== See also ==
* [[Chemistry:Vobasine|Vobasine]]
* [[Chemistry:Isovoacristine|Isovoacristine]]

== References ==
{{Reflist|2}}

{{Opioidergics}}

[[Category:Opioids]]
[[Category:Indole alkaloids]]
[[Category:Alkaloids found in Apocynaceae]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Azocines]]


{{Sourceattribution|Pericine}}