Perrottetinene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Perrottetinene
Perrottetinene.svg
Systematic (IUPAC) name
(6aS,10aR)- 6,6,9-trimethyl- 3-(2-phenylethyl)- 6a,7,8,10a-tetrahydrobenzo[c]chromen- 1-ol
Clinical data
Legal status ?
Identifiers
CAS number 160041-34-9 YesY
ATC code None
PubChem CID 24766094
Chemical data
Formula C24H28O2 
Mol. mass 348.477 g/mol
 YesY (what is this?)  (verify)

Perrottetinene is a naturally occurring cannabinoid compound found in the New Zealand liverwort plant Radula marginata and other species from the Radula genus,[1] along with a number of similar compounds. Its chemical structure closely resembles that of THC, the main active component of marijuana, and it is thought that perrottetinene may also be an active cannabinoid agonist although detailed pharmacological investigation of the compound has yet to be reported.[2][3] Stereoselective synthesis of perrottinene has also been carried out to investigate the activity of its different enantiomers.[4]

References[edit]

  1. ^ Cullmann F, Becker H. Prenylated bibenzyls from the liverwort Radula laxiramea. Zeitschrift Fur Naturforschung. 1999; 54(3-4): 147-150. ISSN 09395075
  2. ^ Toyota M, Kinugawa T, Asakawa Y. Bibenzyl Cannabinoid and Bisbibenzyl Derivative from the Liverwort Radula perrottetii. Phytochemistry 1994; 37(3):859-862.
  3. ^ Toyota M, Shimamura T, Ishii H, Renner M, Braggins J, Asakawa Y. New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata. Chemical and Pharmaceutical Bulletin (Tokyo). 2002 Oct;50(10):1390-2. PMID 12372871
  4. ^ Song Y, Hwang S, Gong P, Kim D, Kim S. Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration. Organic Letters. 2008 Jan 17;10(2):269-71. PMID 18085788