EXP-561

Chemical compound
  • none
Legal statusLegal status
  • In general: uncontrolled
Identifiers
  • 4-phenylbicyclo[2.2.2]octan-1-amine
CAS Number
  • 10206-89-0 checkY
  • hydrochloride: 10207-08-6 checkY
PubChem CID
  • 27696
ChemSpider
  • 25769
UNII
  • 1P958G9T1V
  • hydrochloride: 6S9H885MKF checkY
CompTox Dashboard (EPA)
  • DTXSID20144571 Edit this at Wikidata
Chemical and physical dataFormulaC14H19NMolar mass201.313 g·mol−13D model (JSmol)
  • Interactive image
  • NC12CCC(CC1)(CC2)C3=CC=CC=C3
InChI
  • 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]

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". 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.
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AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
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SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins


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