Delta-8-Tetrahydrocannabinol

Details

• Internal ID: 838b3c94-c746-4436-a052-b740f1548111
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-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/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3/t16-,17-/m1/s1
• InChI Key: HCAWPGARWVBULJ-IAGOWNOFSA-N
• Popularity: 108 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: 5.70
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• DELTA8-Tetrahydrocannabinol
• delta8-THC
• DELTA 8-TETRAHYDROCANNOBINOL
• DELTA-8-THC
• CHEMBL267227
• B49D0HH807
• (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• delta-6-THC
• NSC 134453
• 8-Tetrahydrocannabinol
• delta(sup 6)-Thc
• delta(sup 8)-Thc
• delta-(sup6)-THC
• delta-(sup8)-THC
• delta6-Tetrahydrocannabinol
• UNII-B49D0HH807
• trans-.DELTA.8-Tetrahydrocannabinol
• (-)-delta8-Tetrahydrocannabinol
• NSC-134453
• trans-DELTA8-Tetrahydrocannabinol
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-
• Cannabinol, delta1(6)-tetrahydro-
• delta1(6)-trans-Tetrahydrocannabinol
• BRN 0023921
• (-)-.DELTA.6-3,4-trans-Tetrahydrocannabinol
• 1-trans-delta(sup 8)-Tetrahydrocannabinol
• 1-trans-delta-(sup8)-Tetrahydrocannabinol
• ?8-Tetrahydro Cannabinol
• (-)-delta(sup 8)-trans-Tetrahydrocannabinol
• (-)-delta-(sup8)-trans-Tetrahydrocannabinol
• Cannabinol, 1-trans-delta(sup 8)-tetrahydro-
• Cannabinol, 1-trans-delta-(sup8)-tetrahydro-
• Tetrahydrocannabinols (-)-delta6-3,4-trans-form
• (-)-delta(sup 6)-3,4-trans-Tetrahydrocannabinol
• 5-17-04-00421 (Beilstein Handbook Reference)
• SCHEMBL2762327
• DTXSID20878586
• (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• CHEBI:183415
• HCAWPGARWVBULJ-IAGOWNOFSA-N
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-
• BDBM50067734
• PDSP2_000219
• .DELTA.-8-TETRAHYDROCANNABINOL
• 8-TETRAHYDROCANNABINOL [WHO-DD]
• (-)-Delta-8-THC, 1mg/ml in Ethanol
• (-)-Delta-8-THC, 10mg/ml in Ethanol
• (-)-Delta-8-THC, 50mg/ml in Ethanol
• DELTA(8)-TRANS-TETRAHYDROCANNABINOL
• (-)-Delta-8-THC, 100mg/ml in Ethanol
• DELTA-8-TETRAHYDROCANNABINOL [NFLIS-DRUG]
• DELTA-8-TETRAHYDROCANNABINOL- [NFLIS-DRUG]
• Q27274350
• TETRAHYDROCANNABINOLS (-)-TRANS-.DELTA.8-FORM
• Delta8-Tetrahydrocannabinol 250 microg/mL in Acetonitrile
• TETRAHYDROCANNABINOLS (-)-TRANS-.DELTA.8-FORM [MI]
• (-)-delta 8-Tetrahydrocannabinol (delta8-THC) 100 microg/mL in Methanol
• (-)-delta 8-Tetrahydrocannabinol (delta8-THC) 1000 microg/mL in Methanol
• 6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• (-)-(6aR-trans)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• (-)-delta8-THC6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• (6aR-trans)-6a,7,10,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
• 6,6,9-TRIMETHYL-3-PENTYL-6H,6AH,7H,10H,10AH-BENZO(C)ISOCHROMEN-1-OL
• 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,10,10a-tetrahydro-3-pentyl-6,6,9-trimethyl-, trans(-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.8381	83.81%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5191	51.91%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8359	83.59%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6964	69.64%
P-glycoprotein inhibitior	-	0.4820	48.20%
P-glycoprotein substrate	-	0.5273	52.73%
CYP3A4 substrate	+	0.6890	68.90%
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	+	0.8407	84.07%
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	-	0.9374	93.74%
Skin irritation	-	0.7104	71.04%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7362	73.62%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.5522	55.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.5949	59.49%
Acute Oral Toxicity (c)	III	0.7739	77.39%
Estrogen receptor binding	+	0.6108	61.08%
Androgen receptor binding	+	0.7538	75.38%
Thyroid receptor binding	+	0.6852	68.52%
Glucocorticoid receptor binding	+	0.7740	77.40%
Aromatase binding	+	0.7777	77.77%
PPAR gamma	+	0.7994	79.94%
Honey bee toxicity	-	0.9041	90.41%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6847	68.47%
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	28.5 nM	Ki	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	51.5 nM; 12 nM	Ki; Ki	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL240	Q12809	HERG	95.29%	89.76%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.29%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	89.96%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.04%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.59%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.43%	90.71%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.71%	89.05%
CHEMBL233	P35372	Mu opioid receptor	86.41%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	84.95%	89.63%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.58%	92.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.23%	89.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.39%	96.25%
CHEMBL2996	Q05655	Protein kinase C delta	83.03%	97.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.84%	92.94%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	82.68%	92.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.55%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.01%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.81%	100.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.63%	96.37%
CHEMBL261	P00915	Carbonic anhydrase I	80.33%	96.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.11%	99.17%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 638026
• LOTUS: LTS0010818
• wikiData: Q27274350