(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

• ChemBase ID: 353
• Molecular Formular: C21H30O2
• Molecular Mass: 314.4617
• Monoisotopic Mass: 314.2245802
• SMILES: O1C([C@H]2[C@H](c3c1cc(cc3O)CCCCC)C=C(CC2)C)(C)C
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
• InChI: InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
• InChIKey: CYQFCXCEBYINGO-IAGOWNOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
• IUPAC Traditional name: marinol; THC
• Brand Name: Abbott 40566; Dea No. 7369; Dea No. 7370; Deltanyne; Dronabinol; Dronabinol [Usan:Inn]; Dronabinolum [Latin]; Δ 9-tetrahydrocannabinol; 9-THC; delta-9-tetrahydrocannabinol; delta-9-THC; Marinol
• Synonyms: Dronabinol; Δ9-THC; Δ1-Tetrahydrocannabinol; (-)-Δ9-Tetrahydrocannabinol solution; Δ9-Tetrahydrocannabinol solution; Tetrahydrocannabinol; Dronabinol; (6aR,10aR)- 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; Δ9-trans-Tetrahydrocannabinol; Abbott 40566; Marinol; NSC 134454; QCD 84924; SP 104; THC; Δ9-Tetrahydro Cannabinol; (-)-Δ9-四氢大麻醇; Δ1-四氢大麻醇; Δ9-四氢大麻酚 溶液

Database IDs

• CAS Number: 1972-08-3
• EC Number: 200-578-6; 200-659-6
• MDL Number: MFCD00083207
• PubChem SID: 160963816; 24900224; 24900035; 46508472
• PubChem CID: 16078
• CHEBI ID: 66964
• ATC CODE: A04AD10
• CHEMBL: 465
• Chemspider ID: 15266
• DrugBank ID: DB00470
• IUPHAR ligand ID: 2424
• Unique Ingredient Identifier: 7J8897W37S
• Wikipedia Title: Tetrahydrocannabinol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.342429
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.944095
• LogD (pH = 7.4): 5.9392576
• Log P: 5.944157
• Molar Refractivity: 96.7335 cm^3
• Polarizability: 37.475655 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 7.29
• LOG S: -5.08
• Solubility (Water): 2.63e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0028 mg/mL (23 °C) in water; 2.8 mg/ml; Chloroform
• Apperance: ethanol solution; Thick Brown Oil
• Boiling Point: 157°C (314.6°F)
• Flash Point: 14 °C; 57.2 °F
• Optical Rotation: -152° (ethanol)
• Hydrophobicity(logP): 5.648

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1170; 1230
• German water hazard class: 1; 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11; 11-23/24/25-39/23/24/25
• Safety Statements: 16; 7-16; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H301-H311-H331-H370
• GHS Precautionary statements: P210; P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2; UN 1230 3/PG 2
• Drug Control: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule I; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Admin Routes: Orally, Smoked (or vaporized)
• Bioavailability: 10-35% (inhalation), 6-20% (oral)
• Dependency Liability: 8-10%
• Excretion: 65-80% (feces), 20-35% (urine) as acid metabolites
• Half Life: 1.6-59 h, 25-36 h (orally administered dronabinol)
• Metabolism: mostly hepatic by CYP2C
• Protein Bound: 95-99%
• Legal Status: Schedule I and III (US); Schedule II (CA) (Canada)
• Pregnancy Category: C
• Gene Information: human ... CNR2(1269)mouse ... Cnr1(12801)rat ... Cnr1(25248)

Product Information

• Purity: ≥97% (HPLC); ≥97.0% (HPLC)
• Concentration: ~1 mg/mL in ethanol; ~25 mg/mL; 1.0 mg/mL±5% in methanol; 10 mg/mL in ethanol
• Grade: analytical standard, for drug analysis
• Suitability: corresponds for H-NMR
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H30O2

DETAILS

DrugBank - DB00470

• Drug Groups: illicit; approved
• Description: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound. Dronabinol is a synthetic form of delta-9-THC. [PubChem]
• Indication: For the treatment of anorexia associated with weight loss in patients with AIDS, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments
• Pharmacology: Marinol may has complex effects on the central nervous system (CNS), including cannabinoid receptors. Dronabinol may inhibit endorphins in the emetic center, suppress prostaglandin synthesis, and/or inhibit medullary activity through an unspecified cortical action.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 90 - 95%
• Half Life: Alpha phase: approximately 4 hours; Beta phase: 25-36 hours
• Protein Binding: 97%
• Elimination: Dronabinol and its biotransformation products are excreted in both feces and urine.
• Distribution: * 10 L/kg
• Clearance: * 0.2 L/kg-hr
• External Links: Wikipedia; RxList

Sigma Aldrich - T2386

Biochem/physiol Actions
Agonist at CB1 and CB2 cannabinoid receptors. Hallucinogen; major psychoactive component of marijuana from Cannabis sativa.

Sigma Aldrich - 56296

Packaging
ampoule contains 1.2mL solution

Sigma Aldrich - 91613

Packaging
ampoule contains 1.2mL solution

Toronto Research Chemicals - T293200

It is the principal active constituent of cannabis. Agonist at CB1 and CB2 cannabinoid receptors. Antiemetic; appetite stimulant. Controlled substance (hallucinogen).

REFERENCES

• Rosenkranz, H., et al.: Toxicol., 1416, 2111 (1967)
• Tanda, G., et al.: Eur. J. Pharmacol., 376, 23 (1967)
• Dewey, W.L., et al.: Pharmacol. Rev., 38, 151 (1967)
• Grotenhermen, F., et al.: Clin. Pharmacokinet., 42, 327 (1967)