EXP-561

EXP-561

EXP-561
Systematic (IUPAC) name
4-phenylbicyclo[2.2.2]octan-1-amine
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number
16142-83-9 (hydrochloride monohydrate)
ATC code None
PubChem
ChemSpider
Chemical data
Formula C14H19N 
Mol. mass 201.31 g/mol

EXP-561[1] is a drug which acts as an inhibitor of the reuptake of serotonin, dopamine, and norepinephrine.[2][3][4][5] It was developed in the 1960s by Du Pont[6] and was suggested as a potential antidepressant but failed in trials[7] and was never marketed.[5][8][9][10]

Analogues

The p-bromophenyl analog has been prepared also.[11] According to the reference, the authors conclude that

References

  1. ^ US 3362878 - Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes
  2. ^ Fuller RW, Snoddy HD, Perry KW (November 1976). "Inhibition of amine uptake by 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561) in rats".  
  3. ^ Koe BK (December 1976). "Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain". The Journal of Pharmacology and Experimental Therapeutics 199 (3): 649–61.  
  4. ^ Wong DT, Molloy BB, Bymaster FP (January 1977). "Blockade of monoamine uptake by 1-amino-4-phenylbicyclo(2,2,2)octane (EXP 561) in rat brain and heart". Neuropharmacology 16 (1): 11–5.  
  5. ^ a b Maj J, Skuza G, Sowińska H, Nowak G (1987). "Pharmacological properties of EXP 561, a potential antidepressant drug". Journal of Neural Transmission 70 (1-2): 81–97.  
  6. ^ US Patent 3308160 - PHENYLBICYCLO[Z.Z.Z]OCTANE-L-AMINES AND SALTS THEREOF
  7. ^ INTERNATIONAL REVIEW NEUROBIOLOGY, Volume 12 Page 160
  8. ^ Lehmann HE, Ban TA, Debow SL (June 1967). "A clinical-pharmacological study with EXP 561". Current Therapeutic Research, Clinical and Experimental 9 (6): 306–8.  
  9. ^ Gershon S, Hekimian LJ, Floyd A (February 1968). "Non-correlation of preclinical-clinical evaluation of a prosposed anti-depressant 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561)". Arzneimittel-Forschung 18 (2): 243–5.  
  10. ^ Ross SB, Kelder D (May 1979). "Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum". Acta Pharmacologica Et Toxicologica 44 (5): 329–35.  
  11. ^ Fuller, R. W.; Snoddy, H. D.; Perry, K. W.; Bymaster, F. P.; Wong, D. T. (1978). "Studies on 4-(p-bromophenyl)-bicyclo (2,2,2) octan-1-amine as an inhibitor of uptake into serotonin neurones". Neuropharmacology 17 (10): 815–818.