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. 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): 11–5. 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. (1973). "[Phenylcyclohexylamine and derivatives. IV. Salts of trans-4-phenylcyclohexylamine with -substituted 4-diphenyl- and 4-cyclohexylphenyl acetic acids and their pharmacological activity]". Il Farmaco; Edizione Scientifica. 28 (4): 265–277. ISSN   0430-0920. 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).