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Compound Detail

CHEMBL267227

DELTA-8-TETRAHYDROCANNABINOL
🧪 Phase II
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🧪 Phase II
CCCCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CC=C(C)C[C@@H]21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267227
Name DELTA-8-TETRAHYDROCANNABINOL
Phase Phase II
Structure Type MOL
InChI Key HCAWPGARWVBULJ-IAGOWNOFSA-N

Known Names

.delta.-8-tetrahydrocannabinol .delta.6-thc .delta.8-tetrahydrocannabinol .delta.8-thc 8-tetrahydrocannabinol Delta 8-tetrahydrocannabinol Delta-8-tetrahydrocannabinol Delta-8-tetrahydrocannabinol- Delta-8-thc NSC-134453 Tetrahydrocannabinols (-)-trans-.delta.8-form
7
Targets
30
Activities
3
Assay Types
2
PK Parameters
20
Publications
11
Known Names
2
Indications

Molecular Properties

314.5
MW (Da)
5.74
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.57
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -nab-

Extended Properties

Molecular Formula C21H30O2
MW 314.47
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 2.19

Indications

Neoplasms Marijuana Abuse

Activity Summary

Ki 28 meas. best 7.92
EC50 1 meas. best 6.2
IC50 1 meas. best 6.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 7.92 7.59 12.0 6
Cannabinoid receptor 1
CHEMBL218
 Ki 7.54 7.3843 28.5 7
Cannabinoid receptor 2
CHEMBL5373
 Ki 7.41 7.4083 39.3 6
Cannabinoid receptor
CHEMBL2096981
 Ki 7.36 7.36 44.0 1
Cannabinoid receptor 1
CHEMBL3571
 Ki 7.32 7.1529 47.6 7
Cannabinoid receptor
CHEMBL2111385
 IC50 6.75 6.75 179.0 1
Cannabinoid receptor 1
CHEMBL3571
 EC50 6.2 6.2 631.0 1
Unchecked
CHEMBL612545
 Ki 4.24 4.24 57544.0 1

Pharmacokinetic Data

Parameter Value Units Species
t1/2 - - Rattus norvegicus
t1/2 - - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 12.0 nM 7.92 Displacement of [3H]CP55940 from full length human recombinant CB2 receptor expr... 26000707
Cannabinoid receptor 2 Ki = 25.0 nM 7.6 Binding affinity to human CB2 receptor transfected in HEK293 cells 19230659
Cannabinoid receptor 2 Ki = 25.0 nM 7.6 Binding affinity to CB2 receptor 19250829
Cannabinoid receptor 2 Ki = 25.0 nM 7.6 Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO-K1 cells 18524604
Cannabinoid receptor 1 Ki = 28.5 nM 7.54 Binding affinity to human CB1 receptor transfected in HEK293 cells 19230659
Cannabinoid receptor 1 Ki = 28.5 nM 7.54 Binding affinity to CB1 receptor 19250829
Cannabinoid receptor 1 Ki = 28.5 nM 7.54 Displacement of [3H]CP-55940 from human CB1 receptor expressed in HEK293 cells 18524604
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Binding affinity for Cannabinoid receptor 2 by the ability to displace radiolabe... 12443781
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Inhibition of [3H]CP-55940 binding to cannabinoid receptor 2 of mouse spleen mem... 15999995
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Displacement of [3H]CP-55940 from mouse spleen CB2 receptor 16387492
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Binding affinity to CB2 receptor 17521177
Cannabinoid receptor 2 Ki = 38.9 nM 7.41 Binding affinity to CB2 receptor 17521177
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Displacement of [3H]CP-55940 from CB2 receptor in mouse spleen membrane 18826296
Cannabinoid receptor 2 Ki = 39.3 nM 7.41 Displacement of [3H]CP-55,940 from mouse CB2 receptor expressed in HEK293 cell m... 24286207
Cannabinoid receptor 2 Ki = 39.6 nM 7.4 Binding affinity to mouse spleen CB2 receptor 23865723
Cannabinoid receptor Ki = 44.0 nM 7.36 The affinity of compound for the cannabinoid brain receptor was determined by me... -
Cannabinoid receptor 1 Ki = 47.6 nM 7.32 Binding affinity to CB1 receptor 17521177
Cannabinoid receptor 1 Ki = 47.86 nM 7.32 Binding affinity to CB1 receptor 17521177
Cannabinoid receptor 1 Ki = 47.6 nM 7.32 Binding affinity to rat CB1 receptor 23865723
Cannabinoid receptor 1 Ki = 47.6 nM 7.32 Displacement of [3H]CP-55940 from CB1 receptor in rat brain synaptosome membrane 18826296

Literature References

PubMed DOI Target Context # Activities
26000707 10.1021/acs.jnatprod.5b00065 Mus musculus 10
569207 10.1021/jm00208a014 Mus musculus 7
1323683 10.1021/jm00094a023 Mus musculus 7
6541257 10.1021/jm00376a029 Unchecked 6
1659638 10.1021/jm00115a023 Mus musculus 5
2155318 10.1021/jm00165a024 Mus musculus 3
- 10.1016/S0960-894X(97)10086-5 Mus musculus 3
448686 10.1021/jm00193a025 Canis familiaris 3
24286207 10.1021/jm4016075 Plasma 2
17521177 10.1021/jm0610705 Cannabinoid receptor 2 2
17521177 10.1021/jm0610705 Cannabinoid receptor 1 2
24286207 10.1021/jm4016075 Cannabinoid receptor 2 2
16420041 10.1021/jm0505157 Cannabinoid receptor 1 2
15999995 10.1021/jm058175c Cannabinoid receptor 2 1
26000707 10.1021/acs.jnatprod.5b00065 Cannabinoid receptor 1 1
15999995 10.1021/jm058175c Cannabinoid receptor 1 1
16387492 10.1016/j.bmcl.2005.12.026 Unchecked 1
- 10.1016/S0960-894X(97)10086-5 Cannabinoid receptor 1
12443781 10.1016/s0960-894x(02)00785-0 Cannabinoid receptor 2 1
12443781 10.1016/s0960-894x(02)00785-0 Cannabinoid receptor 1 1

Data from ChEMBL 36 via Core Engine