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Daledalin

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Chemical compound

Pharmaceutical compound

Daledalin
Clinical data

ATC code	None
Identifiers
IUPAC name N-Methyl-3-(3-methyl-1-phenyl-2,3-dihydro-1H-indol-3-yl)propan-1-amine
CAS Number	22136-27-2 23226-37-1 (tosylate)
PubChemCID	31707
ChemSpider	29403
UNII	IT56261A5A
ChEMBL	ChEMBL2110924
CompTox Dashboard(EPA)	DTXSID00865035
Chemical and physical data
Formula	C₁₉H₂₄N₂
Molar mass	280.415 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1cccc2c1C(C)(CN2c3ccccc3)CCCNC

Daledalin (UK-3557-15) is anantidepressant which wassynthesized andtrialed fordepression in the early 1970s, but was never marketed.^[1]^[2]^[3] It is aselective norepinephrine reuptake inhibitor, with no significant effects on thereuptake ofserotonin anddopamine, and noantihistamine oranticholinergic properties.^[2]^[4]

Synthesis

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Daledalin can be prepared by thereduction ofamedalin withdiborane.^[2]

References

[edit]

^Triggle DJ (1997).Dictionary of pharmacological agents. London: Chapman & Hall.ISBN 978-0-412-46630-4.
^^a ^b ^cCañas-Rodriguez A, Leeming PR (July 1972). "N-Phenyl-2-indolinones and N-phenylindolines. A new class of antidepressant agents".Journal of Medicinal Chemistry.15 (7):762–70.doi:10.1021/jm00277a017.PMID 5043876.
^Edwards JG, Ollerenshaw DP (1974). "Daledalin tosylate: a controlled trial in depressive illness".Current Medical Research and Opinion.2 (6):305–12.doi:10.1185/03007997409114763.PMID 4614944.
^Koe BK (December 1976)."Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain".Journal of Pharmacology and Experimental Therapeutics.199 (3):649–661.PMID 994022.

Antidepressants (N06A)

Specificreuptake inhibitors orreceptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic andtetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Amoxapine Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible:Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible:Caroxazone^‡ Mixed:Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible:Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_BTooltip Monoamine oxidase B-selective	Irreversible:Selegiline

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) GABAkine neurosteroids (brexanolone,zuranolone) 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

DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)

Piperazines:DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 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 (¹²³I) 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
Others:Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lafadofensine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine

NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)

Selective norepinephrine reuptake inhibitors:Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine
Norepinephrine–dopamine reuptake inhibitors:Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Serotonin–norepinephrine reuptake inhibitors:Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors:3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g.,cocaine)
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)

SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)

Selective serotonin reuptake inhibitors:6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine 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 CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors:3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g.,cocaine)
Tricyclic antidepressants:Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others:A-80426 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

VMATsTooltip Vesicular monoamine transporters

Others

Unsorted:Cendifensine

DAT enhancers:Luteolin

DAT modulators:Agonist-like:SoRI-9804
SoRI-20040;Antagonist-like:SoRI-20041

See also:Receptor/signaling modulators •Monoamine releasing agents •Adrenergics •Dopaminergics •Serotonergics •Monoamine metabolism modulators •Monoamine neurotoxins

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