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Cannabichromene
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.236.929
UNII
InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
N Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N
N InChI=1/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
Key: UVOLYTDXHDXWJU-UHFFFAOYAG
CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Properties
C 21 H 30 O 2
Molar mass
314.469 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Cannabichromene (CBC ), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,
[1] exhibits
anti-inflammatory properties in vitro , which may, theoretically, contribute to cannabis
analgesic effects.
[2]
It is a
phytocannabinoid , one of the hundreds of
cannabinoids found in the
Cannabis plant.
[3] It bears structural similarity to the other natural cannabinoids, including
tetrahydrocannabinol (THC),
tetrahydrocannabivarin (THCV),
cannabidiol (CBD), and
cannabinol (CBN), among others.
[3]
[4] CBC and
cannabinols are present in cannabis.
[3] It is not scheduled by the
Convention on Psychotropic Substances .
Biosynthesis
Within the
Cannabis plant, CBC occurs mainly as
cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH).
Geranyl pyrophosphate and
olivetolic acid combine to produce
cannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated above 93 °C, CBCA is
decarboxylated , producing CBC. See also the biosynthetic scheme image below.[
citation needed ]
CBC biosynthetic scheme
Pharmacology
Cannabichromene has been hypothesized to affect THC psychoactivity, though in vivo effects have not been demonstrated.
[5] CBC acts on the
TRPV1 and
TRPA1 receptors, interfering with their ability to break down endocannabinoids (chemicals such as
anandamide and
2-AG that the body creates naturally).
[6] [
unreliable source? ] CBC has shown antitumor effects in breast cancer xenoplants in mice.
[7] It also has
anticonvulsant activity in a
mouse model .
[8]
In vitro , CBC binds weakly to
CB1 and
CB2 with binding affinities of 713 nM and 256 nM, respectively, which are significantly lower than that for
THC with 35 nM at CB1.
[9]
[10] acting as an agonist for
cAMP stimulation and an antagonist at
beta-arrestin .
[9] Additionally, CBC is an agonist of
TRPA1 , and less potently
TRPV3 and
TRPV4 .
[3] CBC has two
stereoisomers .
References
^
"Cannabichromene" . PubChem . National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019 .
^ Morales P, Hurst DP, Reggio PH (2017).
"Molecular Targets of the Phytocannabinoids: A Complex Picture" . Progress in the Chemistry of Organic Natural Products . 103 : 103–31.
doi :
10.1007/978-3-319-45541-9_4 .
ISBN
978-3-319-45539-6 .
PMC
5345356 .
PMID
28120232 .
^
a
b
c
d Turner, Sarah E.; Williams, Claire M.;
Iversen, Leslie ; Whalley, Benjamin J. (2017). "Molecular Pharmacology of Phytocannabinoids". In Kinghorn, A. Douglas;
Falk, Heinz ;
Gibbons, Simon ; Kobayashi, Jun'ichi (eds.). Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa . Progress in the Chemistry of Organic Natural Products. Vol. 103.
Springer International Publishing . pp. 61–101.
doi :
10.1007/978-3-319-45541-9_3 .
ISBN
978-3-319-45539-6 .
PMID
28120231 .
^ Aizpurua-Olaizola, Oier; Soydaner, Umut; Öztürk, Ekin; Schibano, Daniele; Simsir, Yilmaz; Navarro, Patricia; Etxebarria, Nestor; Usobiaga, Aresatz (2016).
"Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes" .
Journal of Natural Products . 79 (2): 324–331.
doi :
10.1021/acs.jnatprod.5b00949 .
PMID
26836472 .
^ Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H (September 2005). "Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids". Behavioural Pharmacology . 16 (5–6): 487–96.
doi :
10.1097/00008877-200509000-00023 .
PMID
16148455 .
S2CID
827221 .
^
"What Is CBC (Cannabichromene)?" . CNBS . Retrieved 2019-03-31 .
^ Ligresti, A.; Moriello, A. S.; Starowicz, K.; Matias, I.; Pisanti, S.; De Petrocellis, L.; Laezza, C.; Portella, G.; Bifulco, M.; Di Marzo, V. (2006-09-01). "Antitumor Activity of Plant Cannabinoids with Emphasis on the Effect of Cannabidiol on Human Breast Carcinoma | Journal of Pharmacology and Experimental Therapeutics". Journal of Pharmacology and Experimental Therapeutics . 318 (3): 1375–1387.
doi :
10.1124/jpet.106.105247 .
PMID
16728591 .
S2CID
1341744 .
^ Anderson LL, Ametovski A, Lin Luo J, Everett-Morgan D, McGregor IS, Banister SD, Arnold JC. Cannabichromene, Related Phytocannabinoids, and 5-Fluoro-cannabichromene Have Anticonvulsant Properties in a Mouse Model of Dravet Syndrome. ACS Chem Neurosci . 2021 Jan 20;12(2):330-339.
doi :
10.1021/acschemneuro.0c00677
PMID
33395525
^
a
b Zagzoog, Ayat; Mohamed, Kawthar A.; Kim, Hye Ji J.; Kim, Eunhyun D.; Frank, Connor S.; Black, Tallan; Jadhav, Pramodkumar D.; Holbrook, Larry A.; Laprairie, Robert B. (2020-11-23).
"In vitro and in vivo pharmacological activity of minor cannabinoids isolated from Cannabis sativa" . Scientific Reports . 10 (1): 20405.
doi :
10.1038/s41598-020-77175-y .
ISSN
2045-2322 .
PMC
7684313 .
PMID
33230154 .
^ Rosenthaler, Sarah; Pöhn, Birgit; Kolmanz, Caroline; Nguyen Huu, Chi; Krewenka, Christopher; Huber, Alexandra; Kranner, Barbara; Rausch, Wolf-Dieter; Moldzio, Rudolf (November 2014).
"Differences in receptor binding affinity of several phytocannabinoids do not explain their effects on neural cell cultures" . Neurotoxicology and Teratology . 46 : 49–56.
doi :
10.1016/j.ntt.2014.09.003 .
PMID
25311884 .
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Acrolein
Allicin (
garlic )
Allyl isothiocyanate (
mustard ,
radish ,
horseradish ,
wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (
cannabis )
Cannabidiol (
cannabis )
Cannabigerol (
cannabis )
Cinnamaldehyde (
cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (
cumin )
Curcumin (
turmeric )
Dehydroligustilide (
celery )
Diallyl disulfide
Dicentrine (
Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (
ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (
celery ,
Angelica acutiloba )
Linalool (
Sichuan pepper ,
thyme )
Methylglyoxal
Methyl salicylate (
wintergreen )
N-Methylmaleimide
Nicotine (
tobacco )
Oleocanthal (
olive oil )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (
Dorrigo pepper )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tear gases
Tetrahydrocannabinol (
cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (
onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Allicin (
garlic )
AM404
Anandamide
Bisandrographolide (
Andrographis paniculata )
Camphor (
camphor laurel ,
rosemary ,
camphorweed ,
African blue basil ,
camphor basil )
Cannabidiol (
cannabis )
Cannabidivarin (
cannabis )
Capsaicin (
chili pepper )
Carvacrol (
oregano ,
thyme ,
pepperwort ,
wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (
chili pepper )
Estradiol
Eugenol (
basil ,
clove )
Evodiamine (
Euodia ruticarpa )
Gingerols (
ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (
chili pepper )
Homodihydrocapsaicin (
chili pepper )
Incensole (
incense )
Lysophosphatidic acid
Low
pH (acidic conditions)
Menthol (
mint )
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (
PAVA spray )
Nordihydrocapsaicin (
chili pepper )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g.,
4α-PDD )
Piperine (
black pepper ,
long pepper )
Polygodial (
Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (
Ruta graveolens )
Resiniferatoxin (RTX) (
Euphorbia resinifera /
pooissonii )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tetrahydrocannabivarin (
cannabis )
Thymol (
thyme ,
oregano )
Tinyatoxin (
Euphorbia resinifera /
pooissonii )
Tramadol
Vanillin (
vanilla )
Zucapsaicin
Blockers