DCBFDehydrocannabifuran

Formula

C₂₁H₂₄O₂

Molar mass

308.40 g·mol⁻¹

CAS

-

PubChem CID

59444381

First described

Isolé en 1975 par Friedrich-Fiechtl et Spiteller, qui ont décrit le déhydrocannabifurane et le cannabifurane parmi de nouveaux constituants du haschich. Les deux molécules ont été purifiées par chromatographie en phase gazeuse micropréparative puis chromatographie sur couche mince, et leurs structures établies par spectrométrie de masse et RMN. Le déhydrocannabifurane a été retrouvé en 2008 par l'équipe de Radwan et ElSohly lors d'une étude phytochimique de Cannabis sativa.

Origin

A very minor constituent of Cannabis sativa L., reported mainly in aged hashish and resin extracts rather than in the fresh flower. It was first obtained from an Afghan hashish extract prepared with cyclohexane and methanol, then re-isolated in 2008 from a cannabinoid-rich cannabis variety. The quantities described are at trace level, which largely explains the absence of pharmacological work.

InChIKey

NAGBBYZBIQVPIQ-UHFFFAOYSA-N

Editorial estimate, not clinical.

Dehydrocannabifuran (DCBF) is a minor cannabinoid with a dibenzofuran core: the terpenic ring of cannabidiol is aromatised in it and an oxygen bridge closes a furan ring, so that the molecule is entirely aromatic and does not share the benzo[c]chromene skeleton of the tetrahydrocannabinols. Isolated from hashish in 1975, it is described above all in aged material, which has prompted debate over its status, oxidation product or genuine hemp metabolite, a question that has not been settled. Its pharmacology has never been characterised: no measured affinity for CB1 or CB2, no data on TRPV1, GPR55, PPARγ or 5-HT1A, and the review literature states that nothing is known of the biological profile of this family. There is no pharmacokinetic study, no metabolism data and no toxicological assessment. Human data are entirely lacking, and what is established is limited to the structure of the molecule, its plant origin and its rarity.

Dehydrocannabifuran is the product of no identified hemp enzyme. It is related to cannabidiol: aromatisation of the terpenic ring of CBD into a thymyl group, followed by an oxidative cyclisation that closes a furan ring between the two nuclei, leads to the dibenzofuran skeleton. Its occurrence mainly in aged resins long suggested a mere oxidation artefact, but since cannabidiol is stable in air, the critical inventory by Hanuš and co-workers considers an aromatisation of enzymatic origin, in which case these thymyl-type compounds would be genuine natural products. The question remains open. A biogenetic-type synthesis from cannabidiol was published in 1984, and the cannabifuran class was reconstructed chemically from cannabidiol in 2022.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

Minor phytocannabinoid

Origin

A very minor constituent of Cannabis sativa L., reported mainly in aged hashish and resin extracts rather than in the fresh flower. It was first obtained from an Afghan hashish extract prepared with cyclohexane and methanol, then re-isolated in 2008 from a cannabinoid-rich cannabis variety. The quantities described are at trace level, which largely explains the absence of pharmacological work.

Status

Unscheduled

Cannabinoïde de type dibenzofurane, rangé parmi les cannabinoïdes dits divers, ou de type thymyle. Le squelette n'est plus celui d'un terpénophénol classique : le cycle terpénique du cannabidiol y est aromatisé et une liaison supplémentaire entre un carbone et un oxygène referme un cycle furane entre les deux noyaux aromatiques. Le déhydrocannabifurane porte un groupe isopropényle là où le cannabifurane porte un isopropyle, avec un phénol en position 1, un méthyle en position 6 et une chaîne pentyle en position 3. La molécule est entièrement aromatique et ne possède aucun centre chiral.

L'identification repose sur la chromatographie en phase gazeuse couplée à la spectrométrie de masse, complétée par la RMN lors des travaux d'isolement ; la purification initiale associait chromatographie gazeuse micropréparative et chromatographie sur couche mince. La molécule n'apparaît qu'en traces dans le profilage de résines de cannabis. Aucune méthode de dépistage en matrice biologique n'est décrite, et le déhydrocannabifurane n'est recherché par aucun examen toxicologique de routine.

1. 1.PubChem CID 59444381 : Déhydrocannabifurane (formule, masse, InChIKey, nom IUPAC, synonymes)
2. 2.Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G. Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016;33(12):1357-1392 (cannabifurane et déhydrocannabifurane isolés de haschichs vieillis ; type thymyle ; profil biologique inconnu)PMID 27722705
3. 3.ElSohly MA, Slade D. Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005;78:539-548 (DCBF-C5 classé parmi les cannabinoïdes divers, isolement en 1975 par Friedrich-Fiechtl et Spiteller)
4. 4.Radwan MM, Ross SA, Slade D, Ahmed SA, Zulfiqar F, ElSohly MA. Isolation and characterization of new Cannabis constituents from a high potency variety. Planta Med. 2008 (déhydrocannabifurane réisolé, composé 11)PMID 18283614
5. 5.Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis. Molecules 2021;26(9):2774 (extrait cyclohexane-méthanol de haschich afghan, DCBF-C5 et CBF-C5, type divers)
6. 6.Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants, annexe IV : « Tétrahydrocannabinols, leurs esters, éthers, sels ainsi que les sels des dérivés précités » (Légifrance)