CAS 1972-08-3|THC|Δ9-四氢大麻酚溶液|Δ9-Tetrahydrocannabinol solution|Δ1-四氢大麻醇|(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol|Abbott 40566|Deltanyne|&Delta|Dro...

General Information

Structure

Molecular Formula

C₂₁H₃₀O₂

Molecular Mass

314.4617

Exact Mass

314.2245802

Charge

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

Canonic Smiles

CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C

Isomeric Smiles

O1C([C@H]2[C@H](c3c1cc(cc3O)CCCCC)C=C(CC2)C)(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

5.94

LogD (pH = 5.5)

5.94

Log P

5.94

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.34

Polar Surface Area

29.46

Polarizability

38.94

Molar Refractivity

96.73

LOG S

-5.80

Data Source

Names and Identifiers

IUPAC Traditional name

THC marinol

Synonyms

Δ9-四氢大麻酚溶液Δ9-Tetrahydrocannabinol solutionΔ1-四氢大麻醇DronabinolQCD 84924(6aR,10aR)- 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-olMarinolΔ9-trans-TetrahydrocannabinolNSC 134454THCΔ9-Tetrahydro CannabinolSP 104Abbott 40566DronabinolTetrahydrocannabinolΔ1-Tetrahydrocannabinol(-)-Δ9-Tetrahydrocannabinol solutionΔ9-THC(-)-Δ9-四氢大麻醇Delta(9)-tetrahydrocannabinolDelta(9)-THC3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol1-trans-delta-9-Tetrahydrocannabinol6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olDronabinolumDelta(1)-tetrahydrocannabinolDelta(9)-tetrahydrocannabinolDronabinol(-)-delta9-trans-Tetrahydrocannabinoldelta9-TetrahydrocannabinolTetrahydrocannabinol

IUPAC name

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

Brand Name

Abbott 40566Deltanyne&Deltadelta-9-tetrahydrocannabinolMarinolDea No. 7370Dronabinol [Usan:Inn]DronabinolDea No. 73699-THCdelta-9-THCDronabinolum [Latin]9-tetrahydrocannabinolSyndros

International Nonproprietary Name (INN)

dronabinol

Names and Identifiers

Registration numbers

CAS Number

1972-08-3

CHEMBL

465CHEMBL465

PubChem CID

16078

Unique Ingredient Identifier

7J8897W37S

ATC CODE

A04AD10

PubChem SID

Registration numbers

Properties

Pharmacology Properties

Safety Information

Toxic (T)

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Tetrahydrocannabinol

Sigma Aldrich

T2386

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

91613

Packaging
ampoule contains 1.2mL solution

56296

Packaging
ampoule contains 1.2mL solution

TRC

T293200

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

ChEBI

CHEBI:66964

A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Rosenkranz, H., et al.: Toxicol., 1416, 2111 (1967)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

THC marinol

Synonyms

IUPAC name

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

Brand Name

Abbott 40566Deltanyne&Deltadelta-9-tetrahydrocannabinolMarinolDea No. 7370Dronabinol [Usan:Inn]DronabinolDea No. 73699-THCdelta-9-THCDronabinolum [Latin]9-tetrahydrocannabinolSyndros

International Nonproprietary Name (INN)

dronabinol

References

PubChem Literature

From Data Sources

• 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)

• Rosenkranz, H., et al.: Toxicol., 1416, 2111 (1967)

Bioactivity

PubChem BioAssay

Molecule Details

DrugBank

DB00470

Drug Groups

illicit; approved

Description

Indication

Pharmacology

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]

Wikipedia

Tetrahydrocannabinol

Sigma Aldrich

T2386

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

91613

Packaging
ampoule contains 1.2mL solution

56296

Packaging
ampoule contains 1.2mL solution

TRC

T293200

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

ChEBI

CHEBI:66964