BCPβ-Caryophyllene

Formula

C₁₅H₂₄

Molar mass

204.35 g·mol⁻¹

CAS

87-44-5

PubChem CID

5281515

Origin

A very widespread natural sesquiterpene. It constitutes an important part of the essential oils of black pepper, clove, hops, rosemary and cinnamon, and it is one of the major terpenes of cannabis, where it coexists with the cannabinoids proper. It is also produced industrially for food flavouring and perfumery.

InChIKey

NPNUFJAVOOONJE-GFUGXAQUSA-N

Editorial estimate, not clinical.

Beta-caryophyllene holds a place apart in the pharmacology of hemp: it is a terpene, not a cannabinoid in the chemical sense, and yet it is a genuine cannabinoid ligand. Gertsch and colleagues established in 2008 that it binds selectively to the CB2 receptor with an inhibition constant of 155 nanomolar and behaves there as a functional agonist, while its affinity for the CB1 receptor remains negligible. That selectivity accounts for the complete absence of intoxicating effect, since it is activation of central CB1 that carries that effect, and it places the compound in the sought-after category of selective CB2 agonists, a target studied for inflammation, pain, atherosclerosis and osteoporosis. The authors documented the complete chain, from binding to the in vivo effect. At the receptor, the compound inhibits adenylyl cyclase and triggers calcium transients; on primary human monocytes it attenuates at 500 nanomolar the expression of pro-inflammatory cytokines induced by lipopolysaccharide; in mice, given orally at 5 milligrams per kilogram, it strongly reduces the inflammatory response to carrageenan. The decisive point of the protocol is that this effect disappears in mice lacking the CB2 receptor, which ties the anti-inflammatory action to the receptor and not to a general property of the terpene. The molecule is present in black pepper, clove, hops and cannabis, which makes it the constituent through which an ordinary diet touches the endocannabinoid system.

A bicyclic sesquiterpene arising from the isoprenoid route. Farnesyl pyrophosphate, a fifteen-carbon precursor formed by condensation of isoprene units, is cyclised by a caryophyllene synthase which simultaneously closes a four-carbon ring and a nine-carbon macrocycle. That route is entirely distinct from that of the hemp cannabinoids, which proceed from the condensation of olivetolic acid with geranyl pyrophosphate and retain an aromatic core.

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

Class

ECS modulator (research)

Origin

A very widespread natural sesquiterpene. It constitutes an important part of the essential oils of black pepper, clove, hops, rosemary and cinnamon, and it is one of the major terpenes of cannabis, where it coexists with the cannabinoids proper. It is also produced industrially for food flavouring and perfumery.

Status

Unscheduled

1. 1.Gertsch et coll. 2008 : le bêta-caryophyllène, cannabinoïde alimentaire agoniste sélectif du CB2PMID 18574142
2. 2.Hashiesh et coll. 2021 : revue des propriétés CB2-sélectives et du potentiel thérapeutique du bêta-caryophyllènePMID 34091179