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Details

Stereochemistry ACHIRAL
Molecular Formula C23H21Cl2N5O2
Molecular Weight 469.352
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of JHU-75528 C-11

SMILES

[11CH3]OC1=CC=C(C=C1)C2=C(C#N)C(=NN2C3=C(Cl)C=C(Cl)C=C3)C(=O)NN4CCCCC4

InChI

InChIKey=MCNQUWLLXZZZAC-BJUDXGSMSA-N
InChI=1S/C23H21Cl2N5O2/c1-32-17-8-5-15(6-9-17)22-18(14-26)21(23(31)28-29-11-3-2-4-12-29)27-30(22)20-10-7-16(24)13-19(20)25/h5-10,13H,2-4,11-12H2,1H3,(H,28,31)/i1-1

HIDE SMILES / InChI

Molecular Formula C23H21Cl2N5O2
Molecular Weight 469.352
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

11C-JHU75528 (also known as 11C-OMAR) is a radiotracer with suitable imaging properties for quantification of cannabinoid receptor, CB1R in the human brain. 11C-JHU75528 is participating in an ongoing phase I clinical trial to examine whether the use of cannabis alters CB1R availability in females and if the severity of cannabis withdrawal is correlated with CB1 receptor availability.

Approval Year

PubMed

PubMed

TitleDatePubMed
A new high-yield synthetic route to PET CB1 radioligands [11C]OMAR and its analogs.
2012 Jun 1

Sample Use Guides

Smoked Cannabis plant material (0 and 25 mg THC) will be administered to volunteers who are regular cannabis users. Cannabis users will also complete a PET scan where 20 millicurie of 11C-OMAR (JHU75528)
Route of Administration: Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:32:56 GMT 2023
Edited
by admin
on Sat Dec 16 11:32:56 GMT 2023
Record UNII
8YHH21923L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JHU-75528 C-11
Common Name English
4-CYANO-1-(2,4-DICHLOROPHENYL)-5-(4-(METHOXY-11C)PHENYL)-N-(1-PIPERIDYL)PYRAZOLE-3-CARBOXAMIDE
Systematic Name English
[11C]OMAR
Common Name English
1H-PYRAZOLE-3-CARBOXAMIDE, 4-CYANO-1-(2,4-DICHLOROPHENYL)-5-(4-(METHOXY-11C)PHENYL)-N-1-PIPERIDINYL-
Systematic Name English
11C-OMAR
Common Name English
OMAR C-11
Common Name English
11C-JHU 75528
Common Name English
Code System Code Type Description
FDA UNII
8YHH21923L
Created by admin on Sat Dec 16 11:32:56 GMT 2023 , Edited by admin on Sat Dec 16 11:32:56 GMT 2023
PRIMARY
DRUG BANK
DB14902
Created by admin on Sat Dec 16 11:32:56 GMT 2023 , Edited by admin on Sat Dec 16 11:32:56 GMT 2023
PRIMARY
PUBCHEM
11963742
Created by admin on Sat Dec 16 11:32:56 GMT 2023 , Edited by admin on Sat Dec 16 11:32:56 GMT 2023
PRIMARY
CAS
942063-86-7
Created by admin on Sat Dec 16 11:32:56 GMT 2023 , Edited by admin on Sat Dec 16 11:32:56 GMT 2023
PRIMARY
Related Record Type Details
TARGET->RADIOLIGAND
Related Record Type Details
ACTIVE MOIETY
11C-JHU75528 readily entered the mouse and baboon brain and specifically and selectively labeled cerebral CB1 receptors. The ratio of striatum to brain stem in mice and the binding potential (BP) in the baboon putamen were 3.4 and 1.321.5, respectively. The specific binding of 11C-JHU75528 in vivo was blocked by preinjection of nonlabeled JHU75528. Administration of rimonabant (1 mg/kg, intravenously) also blocked the specific binding of 11C-JHU75528 in the mouse and baboon brain, whereas various central noncannabinoid drugs did not significantly reduce the 11C-JHU75528 binding in the mouse brain. 11C-JHU75528 formed several hydrophilic metabolites, but only a minute fraction of metabolic radioactivity penetrated the BBB.