Tetrahydrocannabinol

Details

• Internal ID: f8c12b65-1e70-4387-973b-fd8db80cb8e7
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• 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
• InChI Key: CYQFCXCEBYINGO-IAGOWNOFSA-N
• Popularity: 16,774 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.50 g/mol
• Exact Mass: 314.224580195 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• TETRAHYDROCANNABINOL
• Marinol
• delta9-Tetrahydrocannabinol
• delta9-THC
• Abbott 40566
• delta-9-tetrahydrocannabinol
• 1972-08-3
• delta-9-THC
• delta(9)-THC
• Dronabinolum
• delta1-THC
• delta(1)-Tetrahydrocannabinol
• delta1-Tetrahydrocannabinol
• 1-trans-delta-9-Tetrahydrocannabinol
• QCD 84924
• SP 104
• delta(9)-Tetrahydrocannabinol
• QCD-84924
• Syndros
• delta(9)-Tetrahydrocannibinol
• (-)-delta9-Tetrahydrocannabinol
• J882F
• SP-104
• 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol
• NSC-134454
• ABBOTT-40566
• DTXSID6021327
• CHEBI:66964
• 7J8897W37S
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-
• SCI-110 component dronabinol
• DTXCID101327
• NSC134454
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-
• Hashish
• delta(1)-THC
• Ganja
• 9-ene-Tetrahydrocannabinol
• (6AR,10AR)-6,6,9-TRIMETHYL-3-PENTYL-6H,6AH,7H,8H,10AH-BENZO[C]ISOCHROMEN-1-OL
• 6H-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-
• 9 ene Tetrahydrocannabinol
• (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo(c)isochromen-1-ol
• 6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-
• RefChem:5782
• Delta9tetrahydrocannabinol
• Tetrahydrocannabinol, Trans
• delta 1-Tetrahydrocannabinol
• A04AD10
• (-)-delta 9-trans-Tetrahydrocannabinol
• Tetrahydrocannabinols (-)-trans-delta9-
• (-)-delta1-3,4-trans-Tetrahydrocannabinol
• Deltanyne
• THC
• (-)-delta9-trans-Tetrahydrocannabinol
• 1-trans-delta9-Tetrahydrocannabinol
• delta(sup 1)-Thc
• delta(sup 9)-Thc
• Namisol
• 9-tetrahydrocannabinol
• .DELTA.9-Tetrahydrocannabinol
• delta(sup 1)-Tetrahydrocannabinol
• delta(sup 9)-Tetrahydrocannabinol
• .DELTA.1-THC
• .DELTA.9-THC
• L-delta1-trans-Tetrahydrocannabinol
• Cannabinol, delta1-tetrahydro-
• CCRIS 4726
• (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• 6465-30-1
• CHEMBL465
• Tetrahydrocannabinols (-)-delta1-3,4-trans-form
• .delta.-9-tetrahydrocannabinol
• Cannabinol, 1-trans-delta(sup 9)-tetrahydro-
• trans-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol
• 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
• Tetrahydrocannabinols (-)-trans-.delta.9-form
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, trans-
• (-)-.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
• (-)-trans-Delta9-THC
• Delta 9-THC
• (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol
• (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
• (-)-.DELTA.9-trans-Tetrahydrocannabinol
• (-)-trans-.DELTA.9-Tetrahydrocannabinol
• Marinol (TN)
• DEA No. 7369
• (-)-delta1-Tetrahydrocannabinol
• delta9-trans-Tetrahydrocannabinol
• trans-delta9-Tetrahydrocannabinol
• delta1-Tetrahydrocannabinol (VAN)
• delta9-Tetrahydrocannabinol (VAN)
• Dronabinol (USP/INN)
• .DELTA.1-Tetrahydrocannabinol
• Tetrahydrocannabinol delta9
• (-)-trans-delta9-Tetrahydrocannabinol
• (-)-trans-Delta1-Tetrahydrocannabinol
• (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
• HSDB 6471
• (6aR-trans)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
• CAT-310
• L-trans-delta9-Tetrahydrocannabinol
• (-)-delta(sup 1)-3,4-trans-Tetrahydrocannabinol
• DRG-0138
• 14C-.DELTA.1-Tetrahydrocannabinol
• trans-.DELTA.9-Tetrahydrocannabinol
• NSC 134454
• .delta.-9-THC
• 1-trans-delta(sup9)-tetrahydrocannabinol
• Dronabinol (Synthetic)
• .delta.(sup9)-THC
• 3ls4
• DRONABINOL [INN]
• (-)-3,4-trans-Delta1-Tetrahydrocannabinol
• 1-trans-.delta.(sup9)-tetrahydrocannabinol
• DRONABINOL [HSDB]
• DRONABINOL [USAN]
• (-)-.delta.(sup9)-trans-Tetrahydrocannabinol
• DRONABINOL [VANDF]
• Epitope ID:224552
• DRONABINOL [MART.]
• SCHEMBL4609
• AD313 component dronabinol
• delta 9-Tetrahydrocannabinol
• delta-9 Tetrahydrocannabinol
• DRONABINOL [WHO-DD]
• AD-313 component dronabinol
• BIDD:GT0427
• Dronabinol [USAN:USP:INN]
• GTPL2424
• Cannabinol, tetrahydro- (6CI)
• DRONABINOL [ORANGE BOOK]
• SCHEMBL29390424
• UNII-7J8897W37S
• BDBM60994
• delta-Tetrahydrocannabinol (THC)
• DRONABINOL [USP MONOGRAPH]
• DTXSID001038830
• US9416103, Delta9-THC
• INT-0010
• (A+/-)-delta9-Tetrahydrocannabinol
• Tox21_112616
• BDBM50007391
• PDSP2_000714
• Cannabinol, Delta1-tetrahydro- (7CI)
• DB00470
• FT28083
• INT-0010/06
• (-)-Delta-9-THC, 1mg/ml in Methanol
• CAS-1972-08-3
• TETRAHYDROCANNABINOL, DELTA-9 TRANS
• NS00000050
• C06972
• Cannabinol, 1-trans-.delta.(sup9)-tetrahydro-
• D00306
• Q190067
• (-)-.DELTA.1-3,4-TRANS-TETRAHYDROCANNABINOL
• (-)-Delta9-THC (Dronabinol) 0.1 mg/ml in Methanol
• (-)-Delta9-THC (Dronabinol) 1.0 mg/ml in Methanol
• (-)-Delta-9-THC (Dronabinol) 5.0 mg/ml in Methanol
• (-)-trans-Delta-9-THC (Dronabinol), 100mg/ml in Ethanol
• (-)-trans-Delta-9-THC (Dronabinol), 10mg/ml in Ethanol
• (-)-trans-Delta-9-THC (Dronabinol), 1mg/ml in Ethanol
• (-)-trans-Delta-9-THC (Dronabinol), 50mg/ml in Ethanol
• Delta9-Tetrahydrocannabinol 250 microg/mL in Acetonitrile
• TETRAHYDROCANNABINOLS (-)-TRANS-.DELTA.9-FORM [MI]
• Delta-9-Tetrahydrocannabinol - 50 mg/ml solution in ethanol
• 6H-Dibenzo[b, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-
• (-)-delta 9-Tetrahydrocannabinol (delta9-THC) 1000 microg/mL in Methanol
• (-)-Delta9-Tetrahydrocannabinol (Delta9-THC) 100 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
• (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
• (6AR,10AR)-6,6,9-TRIMETHYL-3-PENTYL-6A,7,8,10A-TETRAHYDRO-6H-DIBENZO(B,D)PYRAN-1-OL
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.8835	88.35%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5191	51.91%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8550	85.50%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5621	56.21%
P-glycoprotein inhibitior	-	0.4614	46.14%
P-glycoprotein substrate	-	0.6217	62.17%
CYP3A4 substrate	+	0.7426	74.26%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.6771	67.71%
CYP2C9 inhibition	+	0.5352	53.52%
CYP2C19 inhibition	+	0.7683	76.83%
CYP2D6 inhibition	-	0.7307	73.07%
CYP1A2 inhibition	+	0.6567	65.67%
CYP2C8 inhibition	+	0.8466	84.66%
CYP inhibitory promiscuity	+	0.8349	83.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7055	70.55%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9441	94.41%
Skin irritation	-	0.7104	71.04%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.8837	88.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7468	74.68%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.5522	55.22%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8068	80.68%
Acute Oral Toxicity (c)	III	0.7739	77.39%
Estrogen receptor binding	+	0.6471	64.71%
Androgen receptor binding	+	0.7144	71.44%
Thyroid receptor binding	+	0.7558	75.58%
Glucocorticoid receptor binding	+	0.7054	70.54%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.8278	82.78%
Honey bee toxicity	-	0.9181	91.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6747	67.47%
Fish aquatic toxicity	+	0.9880	98.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	2.8 nM; 2.8 nM	IC50; IC50	PMID: 21999614; via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	9.5 nM; 1.5 nM	IC50; EC50	PMID: 21999614; via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	10.2 nM	EC50	via Super-PRED
CHEMBL1075322	Q9Y2T6	G-protein coupled receptor 55	14200 nM	IC50	PMID: 23679955
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	1300 nM	EC50	PMID: 25790278
CHEMBL2384898	Q14330	N-arachidonyl glycine receptor	4610 nM; 4610 nM; 960 nM	EC50; EC50; EC50	PMID: 23679955; DOI: 10.1039/C3MD00394A; via Super-PRED
CHEMBL3401	O75469	Pregnane X receptor	12600 nM; 12600 nM	EC50; EC50	PMID: 20966043; PMID: 20966043

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.92%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	97.48%	89.63%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.54%	92.94%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.95%	95.17%
CHEMBL2996	Q05655	Protein kinase C delta	90.22%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.82%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.29%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	86.21%	96.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.20%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.88%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.50%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.35%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.21%	92.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.78%	99.17%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	84.52%	95.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.38%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.78%	90.71%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.59%	92.68%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.55%	95.56%
CHEMBL5203	P33316	dUTP pyrophosphatase	82.11%	99.18%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.54%	96.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.42%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.11%	93.40%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 16078
• NPASS: NPC96940
• ChEMBL: CHEMBL465
• LOTUS: LTS0171230
• wikiData: Q190067