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Milameline
Clinical data

ATC code	None
Identifiers
IUPAC name (E)-N-methoxy-1-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)methanimine
CAS Number	139886-32-1
PubChem CID	9571002
IUPHAR/BPS	301
ChemSpider	7845468
UNII	R9X77R42FN
CompTox Dashboard (EPA)	DTXSID401028867
ECHA InfoCard	100.220.595
Chemical and physical data
Formula	C₈H₁₄N₂O
Molar mass	154.213 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES N(/OC)=C\C1=C\CCN(C)C1

Milameline (CI-979, PD-129,409, RU-35,926) is a non-selective muscarinic acetylcholine receptor partial agonist with cognition-acting properties that was being investigated for the treatment of Alzheimer's disease, but produced poor results in clinical trials and was subsequently discontinued.^[1]

Changing the O-methyl aldoxime to an O-propargyl oxime instead gives a separate molecule called RU 35986.^[2]

References

^ Sedman AJ, Bockbrader H, Schwarz RD (1995). "Preclinical and phase 1 clinical characterization of CI-979/RU35926, a novel muscarinic agonist for the treatment of Alzheimer's disease". Life Sciences. 56 (11–12): 877–882. doi:10.1016/0024-3205(95)00023-Y. PMID 10188788.
^ Broadley KJ, Kelly DR (2001). "Muscarinic Receptor Agonists and Antagonists". Molecules. 6 (3): 142–193. doi:10.3390/60300142. ISSN 1420-3049. PMC 6236374.

v t e Psychoanaleptics: Anti-dementia agents (ATC code N06D and others)
AChE inhibitor medications	Benzgalantamine Donepezil (+memantine) Galantamine Ipidacrine Rivastigmine Tacrine
Other medications	Aducanumab Bifemelane Donanemab Ginkgo folium Lecanemab Meclofenoxate (centrophenoxine) Memantine (+donepezil) Nicergoline
Experimental BACE inhibitors	Lanabecestat Verubecestat

Muscarinic acetylcholine receptor modulators

mAChRs

Agonists

Antagonists

3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (+formoterol)
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine)
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine)
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
Bevonium
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (+beclometasone/formoterol, +indacaterol, +neostigmine)
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (+salbutamol)
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., femoxetine, paroxetine)
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine)
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine)
Umeclidinium bromide (+vilanterol)
WIN-2299
Xanomeline
Zamifenacin

Precursors
(and prodrugs)

See also: Receptor/signaling modulators; Nicotinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

See also

References