EXP-561

EXP-561
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 4-phenylbicyclo[2.2.2]octan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H19N
Molar mass201.313 g·mol−1
3D model (JSmol)
  • NC12CCC(CC1)(CC2)C3=CC=CC=C3
  • InChI=1S/C14H19N.ClH/c15-14-9-6-13(7-10-14,8-11-14)12-4-2-1-3-5-12;/h1-5H,6-11,15H2;1H
  • Key:LTHJBDQSFIGMAZ-UHFFFAOYSA-N

EXP-561[1] is an investigational drug that 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]

SAR simplification in the molecular structure leads to a compound called 4-Phenylcyclohexylamine [19992-45-1].[11] This is made from 4-phenylcyclohexanone via reduction of the oxime.[12] Such compounds cause a desirable stimulation of the CNS and are antidepressants.[13]

See also

[edit]

References

[edit]
  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". Biochemical Pharmacology. 25 (21): 2409–10. doi:10.1016/0006-2952(76)90039-3. PMID 999731.
  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. PMID 994022.
  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. doi:10.1016/0028-3908(77)90040-5. PMID 834358. S2CID 44365500.
  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. doi:10.1007/BF01252511. PMID 2822850. S2CID 23469131.
  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. PMID 4963065.
  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. PMID 5695389.
  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. doi:10.1111/j.1600-0773.1979.tb02339.x. PMID 474143.
  11. ^ Carenini G, Carissimi M, D'Ambrosio R, Grumelli E, Milla E, Ravenna F. Fenicilcicloesilammine e derivati. IV. Sali della trans-4-fenilciclorsilammina con acidi 4-difenilil- e 4-cicloesilfenilacetici -sostituiti e loro attivitá farmacologiche [Phenylcyclohexylamine and derivatives. IV. Salts of trans-4-phenylcyclohexylamine with -substituted 4-diphenyl- and 4-cyclohexylphenyl acetic acids and their pharmacological activity]. Farmaco Sci. 1973;28(4):265-77. Italian. PMID: 4698884.
  12. ^ Massimo Carissimi & Franco Ravenna, DE1618632 (1971 to Maggioni and C SpA).
  13. ^ Walfred S Saari, US3652769 (1972 to Merck and Co Inc).


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