cannabichromene Chemical Properties

Melting point:

145°C

Boiling point:

394.13°C (rough estimate)

Density 

1.0536 (rough estimate)

refractive index 

1.5404 (estimate)

Flash point:

9℃

storage temp. 

-20°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Oil

pka

9.68±0.40(Predicted)

color 

Crystals

InChI

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

InChIKey

UVOLYTDXHDXWJU-UHFFFAOYSA-N

SMILES

C1(C)(CC/C=C(\C)/C)OC2=CC(CCCCC)=CC(O)=C2C=C1

LogP

8.560 (est)

Safety Information

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

1

HS Code 

9999999999

Toxicity

dni-hmn:lyms 100 mmol/L FEPRA7 36,1748,77

cannabichromene Usage And Synthesis

Background

Discovered in the 1960s, cannabichromene (CBC) is the third most prominent cannabinoid found in the cannabis plant, behind CBD and THC. However, CBC remains obscure, and it’s not well understood. What is known, however, is that CBC has significant potential to treat inflammation and could be immensely useful in the reduction of pain and promoting the growth of new brain cells. CBC works in tandem with other cannabinoids like THC, CBD, CBG and CBN, which ultimately boosts their anti-inflammatory and other therapeutic effects. This contribution to the entourage effect makes CBC a very versatile cannabinoid and one that merits further study.

Description

Cannabichromene (CBC) is one of the most abundant cannabinoids found in the cannabis plant, next to CBD, THC, and CBG. It is particularly abundant in freshly harvested dry-type Cannabis material, and it is the second most abundant cannabinoid in some strains of marijuana growing in the USA. Like CBD, CBG does a poor job of binding to the endocannabinoid system's CB1 and CB2 receptors and is a non-psychoactive compound. Instead, CBC has been observed to have unique interactions with TRPV1 and TRPA1 receptors (vanilloid 1 and ankyrin 1 receptors). It has modest antinociceptive and anti‐inflammatory effects and potentiates some effects of Δ9‐tetrahydrocannabinol in vivo[1–2].

Definition

ChEBI: Cannabichromene is a 1-benzopyran.

Biological Functions

More recently, it has been shown that cannabichromene (CBC) exerts antimicrobial, anti-inflammatory, analgesic and antidepressant-like activity in rodents. Pharmacodynamic studies have shown that CBC, like other plant natural products, is an inhibitor of endocannabinoid cellular reuptake and a weak inhibitor of monoacylglycerol lipase (MAGL) but is also a potent activator of transient receptor potential (TRP) ankyrin 1-type (TRPA1) channels. CBC was also recently found to stimulate the descending pathway of antinociception in the ventrolateral periaqueductal grey, probably through activation of TRPA1, inhibition of endocannabinoid inactivation and subsequent elevation of local endocannabinoid levels, and possibly via potentiation of adenosine signalling[3].

General Description

Cannabichromene (CBC) is a non-psychoactive cannabinoid of Cannabis that reportedly exerts anti-inflammatory, antimicrobial and analgesic activity. This Certified Snap-N-Spike^? solution standard is suitable for cannabichromene testing methods by GC/MS, HPLC or LC-MS/MS for Cannabis potency testing or impurity profiling, pharmaceutical research, and forensic analysis. Cerilliant solution Certified Reference Materials (CRMs) of cannabinoids are supplied in a convenient, quantitative, US DEA-exempt solution format and with TK#s for Canadian customers.

Biological Activity

Cannabichromene (CBC) is a selective CB2 receptor agonist displaying higher efficacy than tetrahydrocannabinol in hyperpolarizing AtT20 cells. CBC can also recruit CB2 receptor regulatory mechanisms. CBC may contribute to the potential therapeutic effectiveness of some cannabis preparations, potentially through CB2 receptor‐mediated modulation of inflammation[2].

Side effects

Dry Mouth: Similar to other cannabinoids, CBC can cause dry mouth. Staying hydrated can help mitigate this effect.
Fatigue: Some users feel tired after taking it, especially in higher doses. It's advisable to start with a low dose and gradually increase it to find the optimal amount.
Digestive Issues: In rare cases, it might cause mild digestive issues such as nausea or diarrhoea. Headache: Some people might experience headaches, particularly when starting or taking higher doses.
Dizziness: Occasional dizziness can occur, especially when standing up too quickly after consuming CBC.

Safety Profile

Poison by intravenous and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. Whenheated to decomposition it emits acrid smoke and irritating fumes

target

NOS | COX | ERK | ATPase

References

[1] Angelo A Izzo. “Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice.” British Journal of Pharmacology 166 4 (2012): 1444–1460.
[2] Michael Udoh. “Cannabichromene is a cannabinoid CB2 receptor agonist.” British Journal of Pharmacology 176 23 (2019): 4537–4547.
[3] Angelo A Izzo. “Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice.” British Journal of Pharmacology 166 4 (2012): 1444–1460.

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