Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H30O2 |
| Molecular Weight | 338.4831 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC(C)=CC[C@@]1([H])C(C)(C)OC3=CC(=CC(O)=C23)C#CCCCCC
InChI
InChIKey=PYCLMAJRHLLHNO-RTBURBONSA-N
InChI=1S/C23H30O2/c1-5-6-7-8-9-10-17-14-20(24)22-18-13-16(2)11-12-19(18)23(3,4)25-21(22)15-17/h11,14-15,18-19,24H,5-8,12-13H2,1-4H3/t18-,19-/m1/s1
| Molecular Formula | C23H30O2 |
| Molecular Weight | 338.4831 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/16387492 | https://www.ncbi.nlm.nih.gov/pubmed/12852753
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/16387492 | https://www.ncbi.nlm.nih.gov/pubmed/12852753
(-)-∆8-Tetrahydrocannabinol (∆8-THC) has a very similar pharmacologic profile as (-)-∆9-tetrahydrocannabinol (∆9-THC), the most active constituent of cannabis. Delta-8-tetrahydrocannabinol (THC) has activity in man similar to that of its double-bond isomer, delta-9-THC. The spatial orientation of the side chain seems to play a pivotal role in cannabinergic activity. Introduction of a triple bond in the benzylic position of the n-heptyl-D8-THC analogue led to the classical cannabinoid AMG-1 with high CB1 and moderate CB2 affinity. AMG-1 is an analgesic drug which is a cannabinoid agonist.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. | 1998 Mar 26 |
|
| Structural modifications of the cannabinoid side chain towards C3-aryl and 1',1'-cycloalkyl-1'-cyano cannabinoids. | 2006 Mar 15 |
|
| The role of fluorine substitution in the structure-activity relationships (SAR) of classical cannabinoids. | 2007 Mar 15 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:11:51 GMT 2023
by
admin
on
Sat Dec 16 18:11:51 GMT 2023
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| Record UNII |
Q7S86DY7UF
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Code System | Code | Type | Description | ||
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10830874
Created by
admin on Sat Dec 16 18:11:51 GMT 2023 , Edited by admin on Sat Dec 16 18:11:51 GMT 2023
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205746-46-9
Created by
admin on Sat Dec 16 18:11:51 GMT 2023 , Edited by admin on Sat Dec 16 18:11:51 GMT 2023
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AMG-1
Created by
admin on Sat Dec 16 18:11:51 GMT 2023 , Edited by admin on Sat Dec 16 18:11:51 GMT 2023
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Q7S86DY7UF
Created by
admin on Sat Dec 16 18:11:51 GMT 2023 , Edited by admin on Sat Dec 16 18:11:51 GMT 2023
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> DERIVATIVE |
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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