Perrottetinene Explained
| Verifiedrevid: | 355283121 |
| Iupac Name: | (6aS,10aR)- 6,6,9-trimethyl- 3-(2-phenylethyl)- 6a,7,8,10a-tetrahydrobenzo[c]chromen- 1-ol |
| Width: | 200 |
| Legal Ca: | Schedule II |
| Legal Br: | List F2 |
| Cas Number: | 160041-34-9 |
| Atc Prefix: | none |
| Pubchem: | 24766094 |
| Chemspiderid: | 28284856 |
| C: | 24 |
| H: | 28 |
| O: | 2 |
| Smiles: | CC1=C[C@H]2c3c(cc(cc3OC([C@H]2CC1)(C)C)CCc4ccccc4)O |
| Stdinchi: | 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 |
| Stdinchikey: | DYHMKBLKWFFFSZ-UXHICEINSA-N |
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 but with a cis rather than trans conformation and a bibenzyl tailchain instead of pentyl.[5] The absolute configuration of perrottetinene was established in 2008 by an enantioselective total synthesis.[6]
Pharmacology
In 2018, a study showed that perrottetinene is mild to moderately psychoactive through activation of the cannabinoid receptor 1. (-)-cis-PET was found to have a binding affinity of 481nM at CB1 and 225nM at CB2 while the unnatural (-)-trans-PET was found to have a binding affinity of 127nM at CB1 and 126nM at CB2, both acting as partial agonists. In terms of binding affinity this study found cis-PET to be over 22x weaker than Delta-9-THC. The same study also reported significantly reduced prostaglandin D2 and E2 brain concentrations in mice after perrottetinene administration.[7]
Perrottetinene is structurally related to machaeriol A and other machaeriols found in Machaerium species.[8]
See also
Notes and References
- Saygin D, Tabib T, Bittar HE, Valenzi E, Sembrat J, Chan SY, Rojas M, Lafyatis R . 6 . Transcriptional profiling of lung cell populations in idiopathic pulmonary arterial hypertension . Pulmonary Circulation . 10 . 1 . 147–150 . 1999-04-01 . 32166015 . 10.1515/znc-1999-3-401 . 7052475 . vanc . free .
- Kumar A, Premoli M, Aria F, Bonini SA, Maccarinelli G, Gianoncelli A, Memo M, Mastinu A . 6 . Cannabimimetic plants: are they new cannabinoidergic modulators? . Planta . 249 . 6 . 1681–1694 . June 2019 . 30877436 . 10.1007/s00425-019-03138-x . 253886986 .
- Toyota M, Kinugawa T, Asakawa Y . 10.1016/S0031-9422(00)90371-6. Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii . Phytochemistry . 37 . 3 . 859–862 . 1994 .
- Toyota M, Shimamura T, Ishii H, Renner M, Braggins J, Asakawa Y . New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata . Chemical & Pharmaceutical Bulletin . 50 . 10 . 1390–1392 . October 2002 . 12372871 . 10.1248/cpb.50.1390 . free .
- Reis MH, Antunes D, Santos LH, Guimarães AC, Caffarena ER . Shared Binding Mode of Perrottetinene and Tetrahydrocannabinol Diastereomers inside the CB1 Receptor May Incentivize Novel Medicinal Drug Design: Findings from an in Silico Assay . ACS Chemical Neuroscience . 11 . 24 . 4289–4300 . December 2020 . 33201672 . 10.1021/acschemneuro.0c00547 . 227038959 .
- Song Y, Hwang S, Gong P, Kim D, Kim S . Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration . Organic Letters . 10 . 2 . 269–271 . January 2008 . 18085788 . 10.1021/ol702692q .
- Chicca A, Schafroth MA, Reynoso-Moreno I, Erni R, Petrucci V, Carreira EM, Gertsch J . Uncovering the psychoactivity of a cannabinoid from liverworts associated with HAVOK . Science Advances . 4 . 10 . eaat2166 . October 2018 . 30397641 . 6200358 . 10.1126/sciadv.aat2166 . 2018SciA....4.2166C .
- Web site: Machaeriol A .
