Perrottetinene

Perrottetinene
Clinical data
ATC code	none;
Legal status
Legal status	BR: List F2 ; CA: Schedule II ;
Identifiers
	IUPAC name (6aS,10aR)- 6,6,9-trimethyl- 3-(2-phenylethyl)- 6a,7,8,10a-tetrahydrobenzo[c]chromen- 1-ol;
CAS Number	160041-34-9 ;
PubChem CID	24766094;
ChemSpider	28284856;
Chemical and physical data
Formula	C24H28O2
Molar mass	348.486 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C[C@H]2c3c(cc(cc3OC([C@H]2CC1)(C)C)CCc4ccccc4)O;
	InChI InChI=1S/C24H28O2/c1-16-9-12-20-19(13-16)23-21(25)14-18(15-22(23)26-24(20,2)3)11-10-17-7-5-4-6-8-17/h4-8,13-15,19-20,25H,9-12H2,1-3H3/t19-,20+/m1/s1; Key:DYHMKBLKWFFFSZ-UXHICEINSA-N;
	(verify)

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] along with a number of similar compounds.[2][3] 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.[4] 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.[5]

References

Cullmann F, Becker H (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.
Toyota M, Kinugawa T, Asakawa Y (1994). "Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii". Phytochemistry. 37 (3): 859. doi:10.1016/S0031-9422(00)90371-6.
Toyota M, Shimamura T, Ishii H, Renner M, Braggins J, Asakawa Y (October 2002). "New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata". Chemical & Pharmaceutical Bulletin. 50 (10): 1390–2. doi:10.1248/cpb.50.1390. PMID 12372871.
Song Y, Hwang S, Gong P, Kim D, Kim S (January 2008). "Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration". Organic Letters. 10 (2): 269–71. doi:10.1021/ol702692q. PMID 18085788.
Chicca A, Schafroth MA, Reynoso-Moreno I, Erni R, Petrucci V, Carreira EM, Gertsch J (October 2018). "Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high". Science Advances. 4 (10): eaat2166. Bibcode:2018SciA....4.2166C. doi:10.1126/sciadv.aat2166. PMC 6200358. PMID 30397641.

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[1] Cullmann F, Becker H (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.

[2] Toyota M, Kinugawa T, Asakawa Y (1994). "Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii". Phytochemistry. 37 (3): 859. doi:10.1016/S0031-9422(00)90371-6.

[3] Toyota M, Shimamura T, Ishii H, Renner M, Braggins J, Asakawa Y (October 2002). "New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata". Chemical & Pharmaceutical Bulletin. 50 (10): 1390–2. doi:10.1248/cpb.50.1390. PMID 12372871.

[4] Song Y, Hwang S, Gong P, Kim D, Kim S (January 2008). "Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration". Organic Letters. 10 (2): 269–71. doi:10.1021/ol702692q. PMID 18085788.

[5] Chicca A, Schafroth MA, Reynoso-Moreno I, Erni R, Petrucci V, Carreira EM, Gertsch J (October 2018). "Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high". Science Advances. 4 (10): eaat2166. Bibcode:2018SciA....4.2166C. doi:10.1126/sciadv.aat2166. PMC 6200358. PMID 30397641.