EXP-561

EXP-561

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 4-phenylbicyclo[2.2.2]octan-1-amine
CAS Number	10206-89-0^Y hydrochloride: 10207-08-6^Y
PubChem CID	27696
ChemSpider	25769
UNII	1P958G9T1V hydrochloride: 6S9H885MKF^Y
CompTox Dashboard (EPA)	DTXSID20144571
Chemical and physical data
Formula	C14H19N
Molar mass	201.313 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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]}

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

• M.G. 6669

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. 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).