From Wikipedia, the free encyclopedia
EXP-561 Routes of administration Oral ATC code Legal status
4-phenylbicyclo[2.2.2]octan-1-amine
CAS Number 10206-89-0 Y 10207-08-6 (hydrochloride) 16142-83-9 (hydrochloride monohydrate )PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 14 H 19 N Molar mass 201.313 g·mol−1 3D model (JSmol )
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 [ ]
^ US 3362878 - Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes
^ 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 .
^ 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 .
^ 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 .
^ a b 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 .
^ US Patent 3308160 - PHENYLBICYCLO[Z.Z.Z]OCTANE-L-AMINES AND SALTS THEREOF
^ INTERNATIONAL REVIEW NEUROBIOLOGY, Volume 12 Page 160
^ 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 .
^ 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 .
^ 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 .
Stimulants
Adamantanes
Adapromine
Amantadine
Bromantane
Memantine
Rimantadine
Adenosine antagonists Alkylamines
Cyclopentamine
Cypenamine
Cyprodenate
Heptaminol
Isometheptene
Levopropylhexedrine
Methylhexaneamine
Octodrine
Propylhexedrine
Tuaminoheptane
Ampakines Arylcyclohexylamines Benzazepines
6-Br-APB
SKF-77434
SKF-81297
SKF-82958
Cathinones Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines Phenylmorpholines Piperazines
2C-B-BZP
3C-PEP
BZP
CM156
DBL-583
GBR-12783
GBR-12935
GBR-13069
GBR-13098
GBR-13119
MeOPP
MBZP
oMPP
Vanoxerine
Piperidines
1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
2-Benzylpiperidine
2-Methyl-3-phenylpiperidine
3,4-Dichloromethylphenidate
4-Benzylpiperidine
4-Fluoromethylphenidate
4-Methylmethylphenidate
Desoxypipradrol
Difemetorex
Diphenylpyraline
Ethylnaphthidate
Ethylphenidate
Methylnaphthidate
Isopropylphenidate
JZ-IV-10
Methylphenidate (Dexmethylphenidate )
Nocaine
Phacetoperane
Pipradrol
Propylphenidate
SCH-5472
Pyrrolidines Racetams
Oxiracetam
Phenylpiracetam
Phenylpiracetam hydrazide
Tropanes Tryptamines Others ATC code : N06B
Antidepressants (N06A )
SSRIs
Citalopram
Escitalopram
Fluoxetine #
Fluvoxamine
Indalpine ‡
Paroxetine
Sertraline
Zimelidine ‡
SNRIs
Desvenlafaxine
Duloxetine
Levomilnacipran
Milnacipran
Tofenacin
Venlafaxine
NRIs
Atomoxetine
Reboxetine
Viloxazine
NDRIs
Amineptine ‡
Bupropion
Nomifensine ‡
NaSSAs SARIs
Etoperidone
Nefazodone
Trazodone
SMS Others
Agomelatine
Amisulpride
Esketamine
Etryptamine ‡
Indeloxazine
flupentixol
Ketamine §
Medifoxamine ‡
Metryptamine ‡
Oxaflozane ‡
Pivagabine ‡
Tandospirone
Teniloxazine
Tianeptine
Tricyclic and tetracyclic antidepressants
TCAs
Amineptine ‡
Amitriptyline #
Amitriptylinoxide
Butriptyline ‡
Clomipramine #
Demexiptiline ‡
Desipramine
Dibenzepin
Dimetacrine ‡
Dosulepin
Doxepin
Imipramine
Imipraminoxide ‡
Iprindole ‡
Lofepramine
Melitracen
Metapramine ‡
Nitroxazepine
Nortriptyline
Noxiptiline
Opipramol
Pipofezine
Propizepine ‡
Protriptyline
Quinupramine ‡
Tianeptine
Trimipramine
TeCAs
Amoxapine
Maprotiline
Mianserin
Mirtazapine
Setiptiline
Others
Monoamine oxidase inhibitors
Non-selective MAOA -selectiveMAOB -selective
Adjunctive therapies
Atypical antipsychotics (aripiprazole , brexpiprazole , lurasidone , olanzapine , quetiapine , risperidone )
Buspirone
Lithium (lithium carbonate , lithium citrate )
Thyroid hormones (triiodothyronine (T3 ), levothyroxine (T4 ))
Miscellaneous
Ademetionine (SAMe )
Hypericum perforatum (St. John's Wort)
Oxitriptan (5-HTP )
Rubidium chloride (RbCl)
Tryptophan
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Monoamine reuptake inhibitors
DAT (DRIs )
Piperazines: DBL-583
GBR-12783
GBR-12935
GBR-13069
GBR-13098
Nefazodone
Vanoxerine
Piperidines: 4-Fluoropethidine
Benocyclidine (BTCP)
Desoxypipradrol
Dexmethylphenidate
Difemetorex
Ethylphenidate
HDMP-28
Methylphenidate
Pethidine (meperidine)
Phencyclidine
Pipradrol
Serdexmethylphenidate
Tenocyclidine
Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone
Tropanes: Altropane
Benzatropine (benztropine)
Brasofensine
CFT
Cocaine
Dichloropane
Difluoropine
Etybenzatropine (ethybenztropine)
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (123 I)
RTI-55
RTI-112
RTI-113
RTI-121
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
Tesofensine
Troparil
Tropoxane
WF-11
WF-23
WF-31
WF-33
NET (NRIs )
Norepinephrine–dopamine reuptake inhibitors: Amineptine
Bupropion
Fencamine
Fencamfamin
Hydroxybupropion
Lefetamine
Levophacetoperane
LR-5182
Manifaxine
Methylphenidate
Nomifensine
O-2172
Radafaxine
Serdexmethylphenidate
Solriamfetol
Tricyclic antidepressants: Amitriptyline
Butriptyline
Cianopramine
Clomipramine
Desipramine
Dosulepin (dothiepin)
Doxepin
Imipramine
Lofepramine
Melitracen
Nortriptyline
Protriptyline
Trimipramine
Tetracyclic antidepressants: Amoxapine
Maprotiline
Mianserin
Oxaprotiline
Setiptiline
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., ketamine , phencyclidine )
Dopexamine
Ephenidine
Ginkgo biloba
Indeloxazine
Nefazodone
Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT (SRIs )
Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone
Litoxetine
Lubazodone
LY-393558
Quipazine
SB-649915
TGBA01AD
Trazodone
Vilazodone
Vortioxetine
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine)
Bicifadine
Desvenlafaxine
Duloxetine
Eclanamine
Levomilnacipran
McN5652
Milnacipran
N-Methyl-PPPA
PPPA
Tofenacin
Venlafaxine
Tricyclic antidepressants: Amitriptyline
Cianopramine
Clomipramine
Cyanodothiepin
Desipramine
Dosulepin (dothiepin)
Doxepin
Imipramine
Lofepramine
Nortriptyline
Pipofezine
Protriptyline
Others:
Amoxapine
Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )
Cyclobenzaprine
Delucemine
Dextromethorphan
Dextrorphan
Efavirenz
Hypidone
Medifoxamine
Mesembrine
Mifepristone
MIN-117 (WF-516)
N-Me-5-HT
Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )
Roxindole
VMATs
Amiodarone
Amphetamines (e.g., amphetamine , methamphetamine , MDMA )
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
Ibogaine
Ketanserin
Lobeline
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)
Others
DAT modulators: Agonist-like: SoRI-9804
; Antagonist-like: SoRI-20041
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
Categories :
Drugs not assigned an ATC code Amines Antidepressants Serotonin–norepinephrine–dopamine reuptake inhibitors Stimulants Experimental drugs Nervous system drug stubs Hidden categories:
Drugs with non-standard legal status Articles without EBI source Chemical pages without DrugBank identifier Articles without KEGG source Articles without InChI source Articles containing unverified chemical infoboxes All stub articles