Dronabinol

Base Information

• Chemical Name: Dronabinol
• CAS No.: 1972-08-3
• Deprecated CAS: 14146-43-1,26108-45-2,5957-27-7,1363-19-5,14146-29-3,1363-19-5,14146-29-3,26108-45-2,5957-27-7
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• European Community (EC) Number: 625-153-6
• NSC Number: 134454
• UNII: 7J8897W37S
• DSSTox Substance ID: DTXSID6021327,DTXSID001038830
• Nikkaji Number: J882F
• Wikipedia: Tetrahydrocannabinol
• Wikidata: Q190067
• NCI Thesaurus Code: C867
• RXCUI: 10402
• Pharos Ligand ID: UX411P34XKA9
• Metabolomics Workbench ID: 42817
• ChEMBL ID: CHEMBL465
• Mol file: 1972-08-3.mol

Synonyms:9 ene Tetrahydrocannabinol;9-ene-Tetrahydrocannabinol;delta(1)-Tetrahydrocannabinol;delta(1)-THC;delta(9)-Tetrahydrocannabinol;delta(9)-THC;Dronabinol;Marinol;Tetrahydrocannabinol;Tetrahydrocannabinol, (6a-trans)-Isomer;Tetrahydrocannabinol, (6aR-cis)-Isomer;Tetrahydrocannabinol, (6aS-cis)-Isomer;Tetrahydrocannabinol, Trans Isomer;Tetrahydrocannabinol, Trans-(+-)-Isomer;Tetrahydrocannabinol, Trans-Isomer;THC

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

Chemical Property of Dronabinol

Chemical Property:

• Appearance/Colour: Thick brown oil
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.528
• Boiling Point: 390.448 °C at 760 mmHg
• PKA: pKa 10.6 (Uncertain)
• Flash Point: 149.334 °C
• PSA: 29.46000
• Density: 1.015 g/cm³
• LogP: 5.73580
• Storage Temp.: 2-8°C
• Water Solubility.: 0.28 g/100 mL at 23 C
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 439

Purity/Quality:

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O
• Isomeric SMILES: CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O
• Recent ClinicalTrials: Tetrahydrocannabinol (THC) and Sleep
• Recent EU Clinical Trials: A randomized double-blind placebo-controlled study of nabiximols in patients with spasticity in multiple sclerosis
• Description: Tetrahydrocannabinol (THC) is the main active compound in marijuana. It comes from the plant Cannabis sativa (cannabis), which is a dioecious (monoecious varieties do exist) annual herb naturally found in many tropic and temperate regions of the world. Many varieties of cannabis exist, and two related species (Cannabis indica and Cannabis ruderalia) are main sources of THC. Cannabis sativa is also known as hemp, although this name is not unique to the species; its stem is a source of fiber that has been used throughout history for hundreds of applications including rope, twine, paper, and cloth. Hemp seeds are edible and high in protein. The seeds are also a source of fatty oil that can be used for food, cosmetics, medicines, and as a fuel source. Cannabis contains chemicals called cannabinoids; of the 60 cannabinoids found in Cannabis, one is THC, , which is the psychoactive ingredient in marijuana. Marijuana is produced from the leaves and fl owers of cannabis, and hashish is a resin collected from the female fl owers. The THC content, which determines the effect of cannabis drugs, varies with plant structure, variety, and preparation. Buds and fl owers specifically cultivated for drug use have greater THC content than leaves. THC content may vary from a few tenths of a percent to more than 10%, but good quality marijuana has a THC content of approximately 10%, and good hashish and hashish oils generally have THC contents between 30% and 80%.
• Uses: Medical marijuana remains a controversial topic, but synthetic THC, dronabinol, marketedunder the trade name Marinol, has been available by prescription since 1986. Th edronabinol analog nabilone is another THC prescription drug marketed under the nameCesamet. Marinol and Cesamet, taken as capsules, have Food Drug Administration approvalas an antinausea agent and appetite stimulant (for AIDS patients), but they are also prescribedfor depression and muscle spasms. In 2005, Canada was the first country to approve Sativex,a cannabis spray that relieves pain in people with multiple sclerosis. Δ9-Tetrahydrocannabinol (Δ9-THC) is a natural psychoactive compound found in plants of the genus Cannabis. This cannabinoid (CB) binds with high affinity to both the central CB1 receptor (Ki = 41 nM) and the peripheral CB2 receptor (Ki = 36 nM). Δ9-THC, working primarily through these receptors, has diverse effects on perception, cognition, pain sensitivity, body temperature, the immune system, fetal development, and more. This product is intended for forensic and research purposes.[Cayman Chemical] It is the principal active constituent of cannabis. Agonist at CB1 and CB2 cannabinoid receptors. Antiemetic; appetite stimulant. Controlled substance (hallucinogen).
• Therapeutic Function: Appetite stimulant
• Clinical Use: Dronabinol (synthetic △9-THC) i s a n antinauseant approved for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetics. A related cannabinoid, nabilone, was introduced in Canada for his indication in 1982.

Technology Process of Dronabinol

There total 177 articles about Dronabinol 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: 78.0%

Methyl tetrahydrocannabinolate (16850-65-0) → 1Δ-Tetrahydrocannabinol (1972-08-3,3556-79-4,6087-73-6,6465-30-1,16849-50-6,17766-02-8,26906-54-7,43009-38-7,69855-10-3)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1016/S0040-4039(00)87498-5

Reference yield: 70.0%

rel-(6aS,10aR)-6a,7,8,10a-tetrahydro-1-methoxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene → (+/-)-cis-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol (1972-08-3,3556-79-4,6087-73-6,6465-30-1,16849-50-6,17766-02-8,26906-54-7,43009-38-7,69855-10-3)

Guidance literature:

With sodium thiomethoxide; In N,N-dimethyl-formamide; at 140 ℃; for 14h;

DOI:10.1021/jo200796b

Reference yield: 65.0%

1-<2',6'-di(methoxymethyloxy)-4'-pentylphenyl>-3,7-dimethylocta-2,6-dien-1-ol → (+/-)-cis-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol (1972-08-3,3556-79-4,6087-73-6,6465-30-1,16849-50-6,17766-02-8,26906-54-7,43009-38-7,69855-10-3)

Guidance literature:

With chloro-trimethyl-silane; tetraethylammonium bromide; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1071/CH9842339

upstream raw materials:

methyl magnesium iodide

1-(2,6-dimethoxy-4-pentylphenyl)prop-2-en-1-ol

(-)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol

3,5-dihydroxyphenol

Downstream raw materials:

11-nor-9-carboxt-Δ-9-tetrahydrocannabinol

cannabitriol

10-ethoxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-benzo[c]chromene-1,9-diol

cannabinol

Refernces

• 1、 Vacek, Jan,Vostalova, Jitka,Papouskova, Barbora,Skarupova, Denisa,Kos, Martin,Kabelac, Martin,Storch, Jan. "Antioxidant function of phytocannabinoids: Molecular basis of their stability and cytoprotective properties under UV-irradiation". . p. 258 - 270. Retrieved 2021.
• 2、 Perrotin-Brunel, Helene,Buijs, Wim,Spronsen, Jaap Van,Roosmalen, Maaike J.E. Van,Peters, Cor J.,Verpoorte, Rob,Witkamp, Geert-Jan. "Decarboxylation of Δ9-tetrahydrocannabinol: Kinetics and molecular modeling". . p. 67 - 73. Retrieved 2011.
• 3、 -. "MASS PRODUCTION AND APPLICATION OF DELTA 8 THC". Paragraph 0105-0109. . Retrieved 2022/03/19.
• 4、 -. "STABLE CANNABINOID COMPOSITIONS". . . Retrieved 2022/01/08.