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EXP-561

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EXP-561
Systematic (IUPAC) name
4-phenylbicyclo[2.2.2]octan-1-amine
Clinical data
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 10206-89-0
16142-83-9 (hydrochloride monohydrate)
ATC code None
PubChem CID 27696
ChemSpider 25769
Chemical data
Formula C14H19N 
Mol. mass 201.31 g/mol
SMILES eMolecules & PubChem

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

[edit] Synthesis

EXP-561 synthesis.gif

  1. Acrylonitrile, Triton B, tBuOH, 1 h @20 °C, 76%
  2. KOH, H2O, reflux overnight, 72%
  3. KOAc, Ac2O, 2 h reflux, then destillation @250 °C, 45%
  4. KOH, EtOH, 20 °C overnight, 73%
  5. NH2NH2, 5 h reflux, then KOH, diethylene glycol, 220 °C, 62%

[edit] References

  1. ^ 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". Biochemical Pharmacology 25 (21): 2409–10. doi:10.1016/0006-2952(76)90039-3. PMID 999731. http://linkinghub.elsevier.com/retrieve/pii/0006-2952(76)90039-3. 
  2. ^ 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. PMID 994022. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=994022. 
  3. ^ 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. doi:10.1016/0028-3908(77)90040-5. PMID 834358. 
  4. ^ 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. doi:10.1007/BF01252511. PMID 2822850. 
  5. ^ US Patent 3308160 - PHENYLBICYCLO[Z.Z.Z]OCTANE-L-AMINES AND SALTS THEREOF
  6. ^ 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. PMID 4963065. 
  7. ^ 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. PMID 5695389. 
  8. ^ 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. PMID 474143. 
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