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 family Radulaceae native to Japan, New Zealand and Costa Rica, namely Cladoradula 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-Perrottetinene was found to have a binding affinity of 481 nM at CB1 and 225 nM at CB2, while the unnatural (-)-trans-perrottetinene was found to more active with binding affinities of 127 nM at CB1 and 126 nM at CB2, both acting as partial agonists. In terms of binding affinity, this study found cis-perrottetinene to be over 22 times 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 .
