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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23N3O2
Molecular Weight 349.427
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MDA-19

SMILES

CCCCCCN1c2ccccc2/C(=N/N=C(c3ccccc3)O)/C1=O

InChI

InChIKey=ZGQHMZCITJHYOW-QOCHGBHMSA-N
InChI=1S/C21H23N3O2/c1-2-3-4-10-15-24-18-14-9-8-13-17(18)19(21(24)26)22-23-20(25)16-11-6-5-7-12-16/h5-9,11-14H,2-4,10,15H2,1H3,(H,23,25)/b22-19-

HIDE SMILES / InChI

Molecular Formula C21H23N3O2
Molecular Weight 349.427
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21554|||Q5UB37
Gene ID: 1268.0
Gene Symbol: CNR1
Target Organism: Homo sapiens (Human)
162.0 nM [Ki]
Target ID: P34972
Gene ID: 1269.0
Gene Symbol: CNR2
Target Organism: Homo sapiens (Human)
43.0 nM [Ki]
Target ID: P20272
Gene ID: 25248.0
Gene Symbol: Cnr1
Target Organism: Rattus norvegicus (Rat)
1.13 µM [Ki]
Target ID: Q9QZN9
Gene ID: 57302.0
Gene Symbol: Cnr2
Target Organism: Rattus norvegicus (Rat)
16.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain.
2008 Aug 28
Pharmacological characterization of a novel cannabinoid ligand, MDA19, for treatment of neuropathic pain.
2010 Jul
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:51:44 UTC 2021
Edited
by admin
on Fri Jun 25 22:51:44 UTC 2021
Record UNII
X83OI5CX2U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MDA-19
Code English
BENZOIC ACID, (2Z)-2-(1-HEXYL-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)HYDRAZIDE
Systematic Name English
N'-((3Z)-1-HEXYL-2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)BENZOHYDRAZIDE
Systematic Name English
Code System Code Type Description
WIKIPEDIA
MDA-19
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
PRIMARY MDA-19 is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB2, with reasonable selectivity over the psychoactive CB1 receptor, though with some variation between species. In animal studies it was effective for the treatment of neuropathic pain, but failed to produce cannabis-like behavioural effects.
FDA UNII
X83OI5CX2U
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
PRIMARY
PUBCHEM
135743701
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
PRIMARY
MANUFACTURER PRODUCT INFORMATION
MDA-19
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
PRIMARY CB2 receptor agonist. Displays 4-fold higher affinity for the human CB2 receptor than the human CB1 receptor (Ki values are 43.3 and 162.4 nM respectively) shows 70-fold affinity for the rat CB2 receptor over the rat CB1 receptor (Ki values are 16.3 and 1130 nM respectively). Attenuates tactile allodynia in a rat model does not affect rat locomotor activity.
CAS
1104302-26-2
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
CAS
1048973-47-2
Created by admin on Fri Jun 25 22:51:44 UTC 2021 , Edited by admin on Fri Jun 25 22:51:44 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY