Perrottetinene
Perrottetinene.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (6aS,10aR)- 6,6,9-trimethyl- 3-(2-phenylethyl)- 6a,7,8,10a-tetrahydrobenzo[c]chromen- 1-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC24H28O2
Molar mass348.486 g·mol−1
3D model (JSmol)
  • CC1=C[C@H]2c3c(cc(cc3OC([C@H]2CC1)(C)C)CCc4ccccc4)O
  • 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][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.[5] The absolute configuration of perrottetinene was established in 2008 by an enantioselective total synthesis.[6] 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.[7]

References

  1. ^ Saygin D, Tabib T, Bittar HE, Valenzi E, Sembrat J, Chan SY, et al. (1999-04-01). "Transcriptional profiling of lung cell populations in idiopathic pulmonary arterial hypertension". Pulmonary Circulation. 10 (1): 147–150. doi:10.1515/znc-1999-3-401. PMC 7052475. PMID 32166015.
  2. ^ Kumar A, Premoli M, Aria F, Bonini SA, Maccarinelli G, Gianoncelli A, et al. (June 2019). "Cannabimimetic plants: are they new cannabinoidergic modulators?". Planta. 249 (6): 1681–1694. doi:10.1007/s00425-019-03138-x. PMID 30877436. S2CID 253886986.
  3. ^ Toyota M, Kinugawa T, Asakawa Y (1994). "Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii". Phytochemistry. 37 (3): 859–862. doi:10.1016/S0031-9422(00)90371-6.
  4. ^ 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): 1390–1392. doi:10.1248/cpb.50.1390. PMID 12372871.
  5. ^ Reis MH, Antunes D, Santos LH, Guimarães AC, Caffarena ER (December 2020). "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. doi:10.1021/acschemneuro.0c00547. PMID 33201672. S2CID 227038959.
  6. ^ 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): 269–271. doi:10.1021/ol702692q. PMID 18085788.
  7. ^ 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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