EXP-561

EXP-561

Systematic (IUPAC) name
4-phenylbicyclo[2.2.2]octan-1-amine
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Number	10206-89-0 16142-83-9 (hydrochloride monohydrate)
ATC code	None
PubChem	CID 27696
ChemSpider	25769
Chemical data
Formula	C14H19N
Molar mass	201.31 g/mol
SMILES NC12CCC(CC1)(CC2)C3=CC=CC=C3

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.
5. 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.
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.