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EXP-561

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
PubChemCID
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 aninvestigational drug that acts as aninhibitor of thereuptake ofserotonin,dopamine, andnorepinephrine.[2][3][4][5] It was developed in the 1960s by Du Pont[6] and was suggested as a potentialantidepressant 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]

See also

[edit]

References

[edit]
  1. ^US 3362878, Snyder JA, "Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes", issued 9 January 1968, assigned to EIDP Inc. 
  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):2409–2410.doi:10.1016/0006-2952(76)90039-3.PMID 999731.
  3. ^BK K (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):649–661.doi:10.1016/S0022-3565(25)30726-3.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):11–15.doi:10.1016/0028-3908(77)90040-5.PMID 834358.S2CID 44365500.
  5. ^abMaj 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 3308160, Snyder JA, "4-Phenylbicyclo[2.2.2]octane-1-amines and salts thereof", issued 7 March 1967, assigned to EIDP Inc. 
  7. ^Davis JM (1970). "Theories of biological etiology of affective disorders". In Pfeiffer CC, Smythies JR (eds.).International Review of Neurobiology. Vol. 12. pp. 145–175.doi:10.1016/s0074-7742(08)60060-4.ISBN 978-0-12-366812-7.PMID 4918142.
  8. ^Lehmann HE, Ban TA, Debow SL (June 1967). "A clinical-pharmacological study with EXP 561".Current Therapeutic Research, Clinical and Experimental.9 (6):306–308.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):243–245.PMID 5695389.
  10. ^Ross SB, Kelder D (May 1979). "Inhibition of3H-dopamine accumulation in reserpinized and normal rat striatum".Acta Pharmacologica et Toxicologica.44 (5):329–335.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 (1973). "[Phenylcyclohexylamine and derivatives. IV. Salts oftrans-4-phenylcyclohexylamine with -substituted 4-diphenyl- and 4-cyclohexylphenyl acetic acids and their pharmacological activity]".Il Farmaco; Edizione Scientifica.28 (4):265–277.PMID 4698884.
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
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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
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


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