EXP-561

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]

Routes of
administrationOral

ATC code

none

Legal status

In general: uncontrolled

CAS Number

10206-89-0^Y
hydrochloride: 10207-08-6^Y

Quick facts Clinical data, Routes ofadministration ...

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

SAR simplification in the molecular structure leads to a compound called 4-Phenylcyclohexylamine [19992-45-1].^[11]

[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]
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 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 of ³H-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 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. PMID 4698884.

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