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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
Structure of AMG-1

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

HIDE SMILES / InChI

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

Description
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.

CNS Activity

Curator's Comment: AMG-1 has shown affinity towards cannabinoid receptor 1 (CB1) in rat and mouse brain

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.65 nM [Ki]
3.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:11:51 UTC 2023
Edited
by admin
on Sat Dec 16 18:11:51 UTC 2023
Record UNII
Q7S86DY7UF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMG-1
Common Name English
6H-DIBENZO(B,D)PYRAN-1-OL, 3-(1-HEPTYN-1-YL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-, (6AR,10AR)-
Systematic Name English
O 964
Common Name English
(6AR,10AR)-3-(1-HEPTYN-1-YL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-6H-DIBENZO(B,D)PYRAN-1-OL
Systematic Name English
Code System Code Type Description
PUBCHEM
10830874
Created by admin on Sat Dec 16 18:11:51 UTC 2023 , Edited by admin on Sat Dec 16 18:11:51 UTC 2023
PRIMARY
CAS
205746-46-9
Created by admin on Sat Dec 16 18:11:51 UTC 2023 , Edited by admin on Sat Dec 16 18:11:51 UTC 2023
PRIMARY
WIKIPEDIA
AMG-1
Created by admin on Sat Dec 16 18:11:51 UTC 2023 , Edited by admin on Sat Dec 16 18:11:51 UTC 2023
PRIMARY
FDA UNII
Q7S86DY7UF
Created by admin on Sat Dec 16 18:11:51 UTC 2023 , Edited by admin on Sat Dec 16 18:11:51 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> DERIVATIVE
TARGET -> AGONIST
TARGET -> AGONIST