Perrottetinene

Perrottetinene
Perrottetinene.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC24H28O2
Molar mass348.477 g/mol g·mol−1
3D model (JSmol)
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Perrottetinene is a naturally occurring cannabinoid compound found in liverworts from the genus Radula native to Japan, New Zealand and Costa Rica, namely Radula perrottetii, Radula marginata and Radula laxiramea,[1][2] along with a number of similar compounds.[3][4] Its chemical structure closely resembles that of THC, the main active component of marijuana. The absolute configuration of perrottetinene was established in 2008 by an enantioselective total synthesis.[5] In 2018, a study showed that perrottetinene is moderately psychoactive through activation of the cannabinoid receptor 1. The same study also reported reduced prostaglandin D2 and E2 brain concentrations in mice after perrottetinene administration.[6]

References[edit]

  1. ^ Cullmann F, Becker H. Prenylated bibenzyls from the liverwort Radula laxiramea. Zeitschrift für Naturforschung. 1999; 54(3-4): 147-150. ISSN 0939-5075
  2. ^ Cullmann, Frank; Becker, Hans (1999-04-01). "Prenylated Bibenzyls from the Liverwort Radula laxiramea". Zeitschrift für Naturforschung C. 54 (3–4): 147–150. doi:10.1515/znc-1999-3-401. ISSN 1865-7125.
  3. ^ Toyota, Masao; Kinugawa, Tomohide; Asakawa, Yoshinoiu (1994). "Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii". Phytochemistry. 37 (3): 859. doi:10.1016/S0031-9422(00)90371-6.
  4. ^ Toyota, Masao; Shimamura, Takuji; Ishii, Hikari; Renner, Matt; Braggins, John; Asakawa, Yoshinori (2002). "New Bibenzyl Cannabinoid from the New Zealand Liverwort Radula marginata". Chemical & Pharmaceutical Bulletin. 50 (10): 1390. doi:10.1248/cpb.50.1390.
  5. ^ Song, Yanling; Hwang, Soonho; Gong, Ping; Kim, Deukjoon; Kim, Sanghee (2008). "Stereoselective Total Synthesis of (−)-Perrottetinene and Assignment of Its Absolute Configuration". Organic Letters. 10 (2): 269. doi:10.1021/ol702692q. PMID 18085788.
  6. ^ Chicca, A.; Schafroth, M. A.; Reynoso-Moreno, I.; Erni, R.; Petrucci, V.; Carreira, E. M.; Gertsch, J. (2018-10-01). "Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high". Science Advances. 4 (10): eaat2166. doi:10.1126/sciadv.aat2166. ISSN 2375-2548.