128413-91-2

Basic information

• Product Name: N-(1R,2R,4S)-Bicyclo[2.2.1]hept-2-yl-N'-o-tolyl-guanidine
• Synonyms: N-(1R,2R,4S)-Bicyclo[2.2.1]hept-2-yl-N'-o-tolyl-guanidine
• CAS NO: 128413-91-2
• Molecular Weight: 243.352
• Mol File: 128413-91-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(1R,2R,4S)-Bicyclo[2.2.1]hept-2-yl-N'-o-tolyl-guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1R,2R,4S)-Bicyclo[2.2.1]hept-2-yl-N'-o-tolyl-guanidine(128413-91-2)
• EPA Substance Registry System: N-(1R,2R,4S)-Bicyclo[2.2.1]hept-2-yl-N'-o-tolyl-guanidine(128413-91-2)

Safety Data

• Hazardous Substances Data: 128413-91-2(Hazardous Substances Data)

Upstream product

• 10532-63-5 N-(o-tolyl)cyanamide 
• 14370-45-7 (+/-)-exo-2-aminonorbornane hydrochloride 

Relevant articles and documents

Synthesis and Structure-Activity Relationships of N,N'-Di-o-tolylguanidine Analogues, High-Affinity Ligands for the Haloperidol-Sensitive ? Receptor

With an eye toward the development of novel atypical antipsychotic agents, we have studied the structure-affinity relationships of N,N'-di-o-tolylguanidine (DTG, 3) and its congeners at the haloperidol-sensitive ? receptor.A number of DTG analogues were synthesized and evaluated in in vitro radioligand displacement experiments with guinea pig brain membrane homogenates, using the highly ?-specyfic radioligands -3 and -(+)-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine and the phencyclidine (PCP) receptor specyfic compounds -N-piperidine and -(+)-5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine.The affinity of N,N'-diarylguanidines for the ? receptor decreases with increasing steric bulk of ortho substituents larger than C2H5.Hydrophobic substituents are generally preferred over similarly positioned hydrophilic ones.Furthermore, electroneutral substituents are preferred over strongly electron donating or withdrawing groups.Significant binding to the ? receptor is usually retained as long as at least one side of the guanidine bears a preferred group (e.g. 2-CH3C6H5).Replacement of one or both aryl rings with certain saturated carbocycles (e.g. cyclohexyl, norbornyl, or adamantyl) leads to a significant increase in affinity.By combining the best aromatic and best saturated carbocyclic substituents in the same molecule, we arrived at some of the most potent ? ligands described to date (e.g.N-exo-2-norbornyl-N'-(2-iodophenyl)guanidine, IC50 = 3 nM vs -3).All of the compounds tested were several orders of magnitude more potent at the ? receptor than at the PCP receptor, with a few notable exceptions.This series of disubstituted guanidines may be of value in the development of potential antipsychotics and in the further pharmacological and biochemical chracterization of the ? receptor.