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1972-08-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:353 http://www.chembase.cn/molecule-353.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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]
&Delta
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
CAS Number
1972-08-3
EC Number
200-659-6
200-578-6
MDL Number
MFCD00083207
PubChem SID
24900224
160963816
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.342429  H Acceptors
H Donor LogD (pH = 5.5) 5.944095 
LogD (pH = 7.4) 5.9392576  Log P 5.944157 
Molar Refractivity 96.7335 cm3 Polarizability 37.475655 Å3
Polar Surface Area 29.46 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 7.29  LOG S -5.08 
Solubility (Water) 2.63e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.0028 mg/mL (23 °C) in water expand Show data source
2.8 mg/ml expand Show data source
Chloroform expand Show data source
Apperance
ethanol solution expand Show data source
Thick Brown Oil expand Show data source
Boiling Point
157°C (314.6°F) expand Show data source
Flash Point
14 °C expand Show data source
57.2 °F expand Show data source
Optical Rotation
-152° (ethanol) expand Show data source
Hydrophobicity(logP)
5.648 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
1170 expand Show data source
1230 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
2 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11 expand Show data source
11-23/24/25-39/23/24/25 expand Show data source
Safety Statements
16 expand Show data source
7-16 expand Show data source
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225 expand Show data source
H301-H311-H331-H370 expand Show data source
GHS Precautionary statements
P210 expand Show data source
P260-P280-P301 + P310-P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1170 3/PG 2 expand Show data source
UN 1230 3/PG 2 expand Show data source
Drug Control
Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland expand Show data source
USDEA Schedule I; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Admin Routes
Orally, Smoked (or vaporized) expand Show data source
Bioavailability
10-35% (inhalation), 6-20% (oral) expand Show data source
Dependency Liability
8-10% expand Show data source
Excretion
65-80% (feces), 20-35% (urine) as acid metabolites expand Show data source
Half Life
1.6-59 h, 25-36 h (orally administered dronabinol) expand Show data source
Metabolism
mostly hepatic by CYP2C expand Show data source
Protein Bound
95-99% expand Show data source
Legal Status
Schedule I and III (US) expand Show data source
Schedule II (CA) (Canada) expand Show data source
Pregnancy Category
C expand Show data source
Gene Information
human ... CNR2(1269)mouse ... Cnr1(12801)rat ... Cnr1(25248) expand Show data source
Purity
≥97% (HPLC) expand Show data source
≥97.0% (HPLC) expand Show data source
Concentration
~1 mg/mL in ethanol expand Show data source
~25 mg/mL expand Show data source
1.0 mg/mL±5% in methanol expand Show data source
10 mg/mL in ethanol expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
corresponds for H-NMR expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C21H30O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00470 external link
Item Information
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 external link
Biochem/physiol Actions
Agonist at CB1 and CB2 cannabinoid receptors. Hallucinogen; major psychoactive component of marijuana from Cannabis sativa.
Sigma Aldrich - 56296 external link
Packaging
ampoule contains 1.2mL solution
Sigma Aldrich - 91613 external link
Packaging
ampoule contains 1.2mL solution
Toronto Research Chemicals - T293200 external link
It is the principal active constituent of cannabis. Agonist at CB1 and CB2 cannabinoid receptors. Antiemetic; appetite stimulant. Controlled substance (hallucinogen).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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