Natural Product (NP) Details

General Information of the NP (ID: NP0718)
Name
Delta-9-tetrahydrocannabinol
Synonyms
Dronabinol; TETRAHYDROCANNABINOL; Marinol; delta9-Tetrahydrocannabinol; delta9-THC; delta-9-tetrahydrocannabinol; Deltanyne; 1972-08-3; Abbott 40566; delta-9-THC; delta(9)-THC; delta1-THC; Dronabinolum; THC; delta(1)-Tetrahydrocannabinol; delta(9)-Tetrahydrocannabinol; 1-trans-delta-9-Tetrahydrocannabinol; delta(sup 1)-Thc; delta(sup 9)-Thc; Namisol; (-)-delta9-trans-Tetrahydrocannabinol; 9-tetrahydrocannabinol; QCD 84924; SP 104; delta1-Tetrahydrocannabinol; 1-trans-delta9-Tetrahydrocannabinol; delta(9)-Tetrahydrocannibinol; QCD-84924; Syndros; delta(sup 1)-Tetrahydrocannabinol; delta(sup 9)-Tetrahydrocannabinol; L-delta1-trans-Tetrahydrocannabinol; Cannabinol, delta1-tetrahydro-; CCRIS 4726; (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; CHEBI:66964; 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol; CHEMBL465; Tetrahydrocannabinols (-)-delta1-3,4-trans-form; (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol; UNII-7J8897W37S; Cannabinol, 1-trans-delta(sup 9)-tetrahydro-; 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; 7J8897W37S; NSC-134454; Dronabinolum [Latin]; Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol; 6,6,9-Trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-dibenzo(b,d)pyran-1-ol; 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-; .DELTA.9-Tetrahydrocannabinol; (-)-.DELTA.9-THC; Compassia; Relivar; (L)-.delta.1-Tetrahydrocannabinol; (-)-.DELTA.1-Tetrahydrocannabinol; (-)-.DELTA.9-Tetrahydrocannabinol; L-.delta.1-trans-Tetrahydrocannabinol; L-trans-.delta.9-Tetrahydrocannabinol; (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol; (6aR-trans)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol; 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-; 6H-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-; (-)-.DELTA.9-trans-Tetrahydrocannabinol; (-)-trans-.DELTA.9-Tetrahydrocannabinol; Marinol (TN); DEA No. 7369; .DELTA.1-THC; .DELTA.9-THC; delta1-Tetrahydrocannabinol (VAN); delta9-Tetrahydrocannabinol (VAN); Dronabinol (USP/INN); .DELTA.1-Tetrahydrocannabinol; Tetrahydrocannabinol delta9; (-)-trans-Delta9-THC; (l)-delta(sup 1)-Tetrahydrocannabinol; Cannabinol, .DELTA.1-tetrahydro-; 1-trans-delta(sup 9)-Tetrahydrocannabinol; .DELTA.9-trans-Tetrahydrocannabinol; (l)-delta1-Tetrahydrocannabinol; L-.delta.1-Tetrahydrocannabinol; (-)-delta1-Tetrahydrocannabinol; (-)-delta9-Tetrahydrocannabinol; delta9-trans-Tetrahydrocannabinol; HSDB 6471; trans-delta9-Tetrahydrocannabinol; (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; (6aR-trans)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; CAT-310; 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, trans-; L-trans-delta9-Tetrahydrocannabinol; (-)-delta(sup 1)-3,4-trans-Tetrahydrocannabinol; 6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-; DRG-0138; 14C-.DELTA.1-Tetrahydrocannabinol; trans-.DELTA.9-Tetrahydrocannabinol; (-)-trans-Delta1-Tetrahydrocannabinol; (-)-trans-delta9-Tetrahydrocannabinol; NSC 134454; .delta.-9-THC; 1-trans-delta(sup9)-tetrahydrocannabinol; .delta.(sup9)-THC; 3ls4; (-)-3,4-trans-Delta1-Tetrahydrocannabinol; 1-trans-.delta.(sup9)-tetrahydrocannabinol; DSSTox_CID_1327; (-)-.delta.(sup9)-trans-Tetrahydrocannabinol; Epitope ID:224552; SCHEMBL4609; delta 9-Tetrahydrocannabinol; delta-9 Tetrahydrocannabinol; DSSTox_RID_76083; trans-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol; DSSTox_GSID_21327; BIDD:GT0427; Dronabinol [USAN:USP:INN]; ABBOTT-40566; GTPL2424; Cannabinol, tetrahydro- (6CI); DTXSID6021327; BDBM60994; J882F; US9416103, Delta9-THC; INT-0010; ZINC1530625; Tox21_112616; BDBM50007391; NSC134454; PDSP2_000714; SP-104; Cannabinol, Delta1-tetrahydro- (7CI); DB00470; INT-0010/06; (-)-Delta9-Tetrahydrocannabinol solution; 6465-30-1; CAS-1972-08-3; Synthetic THC in sesame oil / soft gelatin; C06972; Cannabinol, 1-trans-.delta.(sup9)-tetrahydro-; D00306; Tetrahydrocannabinols (-)-trans-.delta.9-form; 23623-EP2269989A1; 23623-EP2275420A1; 23623-EP2298764A1; 23623-EP2298765A1; 23623-EP2298772A1; 23623-EP2308839A1; 23623-EP2314298A1; 23623-EP2314580A1; Dronabinol in sesame oil in soft gelatin capsule; 124699-EP2272825A2; 124699-EP2289509A2; 124699-EP2295426A1; 124699-EP2295427A1; 148820-EP2289509A2; Q190067; (-)-Delta9-THC (Dronabinol) 0.1 mg/ml in Methanol; (-)-Delta9-THC (Dronabinol) 1.0 mg/ml in Methanol; (-)-Delta9-THC (Dronabinol) 5.0 mg/ml in Methanol; Delta9-Tetrahydrocannabinol solution, ethanol solution; UNII-K4H93P747O component CYQFCXCEBYINGO-IAGOWNOFSA-N; 6H-Dibenzo[b, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-; (-)-Delta9-Tetrahydrocannabinol (Delta9-THC) 100 microg/mL in Methanol; (-)-Delta9-Tetrahydrocannabinol (Delta9-THC) 1000 microg/mL in Methanol; 6,9-Trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran-1-ol; 6H-Dibenzo[b, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, trans-; (-)-(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; (-)-delta(sup 1)-3,4-trans-Tetrahydrocannabinol(l)-delta(sup 1)-Tetrahydrocannabinol; (10R,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; (6AR,10AR)-6,6,9-TRIMETHYL-3-PENTYL-6H,6AH,7H,8H,10AH-BENZO[C]ISOCHROMEN-1-OL; (S)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol(DeltaE-9-THC); 6H-Dibenzo[b, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-; Delta-9-Tetrahydrocannabinol, United States Pharmacopeia (USP) Reference Standard; (-)-Delta9-Tetrahydrocannabinol solution, ~1 mg/mL in ethanol, analytical standard, for drug analysis; (-)-trans-Delta9-THC solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material; 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol(delta9-THC(delta9-tetrahydrocannabinol)); 8,8-Dimethyl-11-methylene-5-pentyl-3,4,8a,9,10,11,12,12a-octahydro-2H,8H-1,7-dioxa-benzo[c]phenanthrene; Delta9-Tetrahydrocannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis
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Species Origin Cannabis sativa ...     Click to Show/Hide
Cannabis sativa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Rosales
Family: Cannabaceae
Genus: Cannabis
Species: Cannabis sativa
Disease Anorexia nervosa [ICD-11: 6B80] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.852
 
MDCK Permeability
 -4.683
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 0.809
 
PPB
 96.5%
 
BBB
 +++
 
Metabolism
CYP1A2 inhibitor
 - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 +
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 3.548
 
T1/2
 0.759
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 +
 
Respiratory
 +++
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 -
 
Hematotoxicity
 -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C21H30O2
PubChem CID
16078
Canonical SMILES
CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O
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
CAS Number
CAS 1972-08-3
ChEBI ID
CHEBI:66964
Herb ID
HBIN023188
SymMap ID
SMIT18298
TTD Drug ID
D0P1FO
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Memantine      Alzheimer disease     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Haloperidol-induced tremulous jaw movements (TJMs) in rats were used as a model of parkinsonian-like tremor.
                    Experimental
                    Result(s)		 Memantine and THC supra-additively inhibit haloperidol-induced TJMs, suggesting that co-administration of these drugs might be a new approach to the treatment of tremor.
          Temozolomide      Brain cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
T98G CVCL_0556 Glioblastoma Homo sapiens
HG19 cells isolated from brain tumor biopsies Brain tumor Homo sapiens
                    In-vivo Model Tumors were induced in nude mice by subcutaneous injection of 5 * 106 U87 cells or 10 *106 T98 cells in PBS supplemented with 0.1% glucose.
                    Experimental
                    Result(s)		 The combined administration of Delta(9)-Tetrahydrocannabinol and temozolomide exerts a strong antitumoral action in glioma xenografts, an effect that is also observed in tumors that are resistant to TMZ treatment.
Target and Pathway
Target(s) Cannabinoid receptor 1 (CB1)  Molecule Info  [4]
KEGG Pathway Rap1 signaling pathway Click to Show/Hide
2 Neuroactive ligand-receptor interaction
3 Retrograde endocannabinoid signaling
Panther Pathway Endogenous cannabinoid signaling Click to Show/Hide
Pathway Interaction Database N-cadherin signaling events Click to Show/Hide
Reactome Class A/1 (Rhodopsin-like receptors) Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways GPCRs, Class A Rhodopsin-like Click to Show/Hide
2 Small Ligand GPCRs
3 BDNF signaling pathway
4 GPCR ligand binding
5 GPCR downstream signaling
6 GPCRs, Other
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018651.
Reference 2 Neuroanatomical correlates of the inhibition of tremulous jaw movements in rats by a combination of memantine and Delta 9 -tetrahydrocannabinol. Br J Pharmacol. 2020 Apr;177(7):1514-1524.
Reference 3 A combined preclinical therapy of cannabinoids and temozolomide against glioma. Mol Cancer Ther. 2011 Jan;10(1):90-103.
Reference 4 Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411.
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