Cannabinol

Base Information

• Chemical Name: Cannabinol
• CAS No.: 521-35-7
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.436
• Hs Code.: 2906299090
• European Community (EC) Number: 689-788-0
• NSC Number: 134455
• UNII: 7UYP6MC9GH
• DSSTox Substance ID: DTXSID3048996
• Nikkaji Number: J6.613C
• Wikipedia: Cannabinol
• Wikidata: Q265831
• NCI Thesaurus Code: C84510
• Pharos Ligand ID: UXZ316M2HWTX
• Metabolomics Workbench ID: 27990
• ChEMBL ID: CHEMBL74415
• Mol file: 521-35-7.mol

Synonyms:Cannabinol

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Cannabinol

Chemical Property:

• Appearance/Colour: thin platelets
• Vapor Pressure: 1.06E-09mmHg at 25°C
• Melting Point: 76 - 77 C
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 476.5 °C at 760 mmHg
• PKA: 9.40±0.40(Predicted)
• Flash Point: 212.7 °C
• PSA: 29.46000
• Density: 1.061 g/cm³
• LogP: 5.72780
• Storage Temp.: 2-8°C
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 310.193280068
• Heavy Atom Count: 23
• Complexity: 391

Purity/Quality:

Safty Information:

• Pictogram(s): FT
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC1=CC(=C2C(=C1)OC(C3=C2C=C(C=C3)C)(C)C)O
• Recent ClinicalTrials: Cannabinol Use in Patients With Insomnia Disorder
• Recent EU Clinical Trials: A Randomised, Double-Blind, Vehicle-Controlled Phase 2 Study of Topically Applied INM-755 (cannabinol) Cream in Patients with Epidermolysis Bullosa.
• Uses: A metabolite of Tetrahydrocannabinol (T293200). A psychoactive substance cannabinoid that acts as a weak agonist of the CB1 and CB2 receptors.

Technology Process of Cannabinol

There total 56 articles about Cannabinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-hydroxy-9-methyl-3-pentyl-6H-dibenzopyran-6-one (63839-83-8) + methyllithium (917-54-4) → cannabinol (521-35-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201805961

Reference yield: 95.0%

8-acetyl-1-methoxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran (1352573-55-7) → cannabinol (521-35-7)

Guidance literature:

With hydrogen iodide; acetic anhydride; at 120 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol2030636

Reference yield: 89.0%

9-methyl-3-pentyl-1-(prop-2-yn-1-yloxy)-6H-benzo[c]chromen-6-one (1601476-46-3) + methyllithium (917-54-4) → cannabinol (521-35-7)

Guidance literature:

9-methyl-3-pentyl-1-(prop-2-yn-1-yloxy)-6H-benzo[c]chromen-6-one; methyllithium; In diethyl ether; at -10 - 20 ℃; for 4h; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/adsc.201301037

upstream raw materials:

methyl magnesium iodide

1-hydroxy-9-methyl-3-pentyl-6H-dibenzopyran-6-one

cannabinol tert-butyldimethylsilyl ether

tetrahydrocannabinol

Downstream raw materials:

cannabinolic acid

Refernces

• 1、 Meltzer,Dalzell,Razdan. "An improved synthesis of cannabinol and cannabiorcol". . p. 985 - 987. Retrieved 1981.
• 2、 Kayser, Oliver,Nguyen, Gia-Nam,Pitakbut, Thanet. "Activity of THC, CBD, and CBN on Human ACE2 and SARS-CoV1/2 Main Protease to Understand Antiviral Defense Mechanism". . . Retrieved 2021/10/21.
• 3、 -. "METHODS FOR PREPARING CANNABINOIDS AND RELATED INSTRUMENTS". Paragraph 0061; 0062. . Retrieved 2021/10/15.