Igmesine

Igmesine
Clinical data

ATC code	none
Identifiers
IUPAC name (E)-N-(cyclopropylmethyl)-N-ethyl-3,6-diphenylhex-5-en-3-amine
CAS Number	140850-73-3^Y
PubChem (CID)	6438340
ChemSpider	4942823^N
UNII	XA3745J38K^Y
Chemical and physical data
Formula	C₂₃H₂₉N
Molar mass	319.483 g/mol
3D model (Jmol)	Interactive image
SMILES N(C(c1ccccc1)(CC)C\C=C\c2ccccc2)(C)CC3CC3
InChI InChI=1S/C23H29N/c1-3-23(22-14-8-5-9-15-22,24(2)19-21-16-17-21)18-10-13-20-11-6-4-7-12-20/h4-15,21H,3,16-19H2,1-2H3/b13-10+^N Key:VCZSWYIFCKGTJI-JLHYYAGUSA-N^N
^NY (what is this?) (verify)

Igmesine (JO-1,784) is a sigma receptor agonist.^[1] It has neuroprotective and antidepressant effects in animal studies,^[2]^[3] as well as nootropic effects in models of age-related cognitive decline.^[4] It showed good results in phase I human clinical trials but has not been continued further.^[5]

References

↑ Roman FJ, Pascaud X, Martin B, Vauché D, Junien JL (June 1990). "JO 1784, a potent and selective ligand for rat and mouse brain sigma-sites". The Journal of Pharmacy and Pharmacology. 42 (6): 439–40. doi:10.1111/j.2042-7158.1990.tb06588.x. PMID 1979628.
↑ O'Neill M, Caldwell M, Earley B, Canney M, O'Halloran A, Kelly J, Leonard BE, Junien JL (September 1995). "The sigma receptor ligand JO 1784 (igmesine hydrochloride) is neuroprotective in the gerbil model of global cerebral ischaemia". European Journal of Pharmacology. 283 (1-3): 217–25. doi:10.1016/0014-2999(95)00356-P. PMID 7498313.
↑ Akunne HC, Zoski KT, Whetzel SZ, Cordon JJ, Brandon RM, Roman F, Pugsley TA (July 2001). "Neuropharmacological profile of a selective sigma ligand, igmesine: a potential antidepressant". Neuropharmacology. 41 (1): 138–49. doi:10.1016/S0028-3908(01)00049-1. PMID 11445194.
↑ Maurice T, Roman FJ, Su TP, Privat A (September 1996). "Beneficial effects of sigma agonists on the age-related learning impairment in the senescence-accelerated mouse (SAM)". Brain Research. 733 (2): 219–30. doi:10.1016/0006-8993(96)00565-3. PMID 8891305.
↑ Volz HP, Stoll KD (November 2004). "Clinical trials with sigma ligands". Pharmacopsychiatry. 37 Suppl 3: S214–20. doi:10.1055/s-2004-832680. PMID 15547788.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

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	Mianserin Mirtazapine Setiptiline

SARIs	Etoperidone Nefazodone^‡ Trazodone

SMSs	Vilazodone Vortioxetine

Others	Agomelatine Amisulpride Amitriptyline/perphenazine Buprenorphine Bupropion Etryptamine^‡ Flupentixol/melitracen Esketamine Ketamine Indeloxazine Lurasidone Medifoxamine^‡ Metryptamine^‡ Olanzapine/fluoxetine Oxaflozane^‡ Quetiapine Tandospirone Teniloxazine Tianeptine Tranylcypromine/trifluoperazine

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	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tranylcypromine Reversible: Caroxazone^‡

MAO_A-selective	Reversible: Bifemelane Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone

MAO_B-Selective	Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics (aripiprazole, lurasidone, olanzapine, quetiapine) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous

Ademetionine (SAMe) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Nootropics

Ampakines	CX-516 CX-546 CX-614 Farampator (CX-691) CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986

Cholinergics	mAChR agonists: 77-LH-28-1 ADX-47273 Alvameline Arecoline Cevimeline CI-1017 Milameline Sabcomeline Tazomeline Xanomeline nAChR agonists: AR-R17779 Bradanicline Cotinine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-282,987 Pozanicline Rivanicline SIB-1553A SSR-180,711 TC-1827 WAY-317,538 AChE inhibitors: Celastrus paniculatus Cymserine Donepezil Galantamine Huperzine A (Huperzia Serrata) Ladostigil Metrifonate Physostigmine Rivastigmine Tacrine Others: Alpha-GPC Choline Dimethylethanolamine Citicoline

Racetams	Aniracetam Brivaracetam Coluracetam Etiracetam Fasoracetam Levetiracetam Nebracetam Nefiracetam Oxiracetam Phenylpiracetam Piracetam Pramiracetam Rolziracetam Seletracetam

Nutrients	Acetylcarnitine Choline Omega-3 fatty acids Magnesium threonate Phosphatidylserine Pyritinol Sulbutiamine Thiamine

Others	Aceglutamide Adafenoxate Bacopa monnieri BAY 73-6691 Bifemelane Bilobalide (Ginkgo biloba) C16 Carbenoxolone Centella asiatica Cinnarizine Ciproxifan Clitoria ternatea Cyprodenate Dihexa Edaravone Eleutherococcus senticosus Ergoloid Ensaculin Emoxypine Fipexide Ginseng Guarana Idebenone Indeloxazine ISRIB Leteprinim Linopirdine Meclofenoxate (centrophenoxine) Methylene blue Nizofenone Noopept NSI-189 P7C3 Pirisudanol Pitolisant PRL-8-53 Razobazam Rubidium S-17092 Semax Shilajit Suritozole Taltirelin Teniloxazine Tianeptine Tricyanoaminopropene Uncaria tomentosa Vincamine Vinpocetine

Sigma receptor modulators

Agonists	3-MeO-PCE 3-MeO-PCP 3-PPP 4-MeO-PCP 4-IBP 4-PPBP Afobazole Alazocine Amantadine Amitriptyline Arketamine BD-1008 BD1031 BD1052 Berberine Buprenorphine Captodiame Citalopram Clorgiline Cocaine Cutamesine Cyclazocine DHEA DHEA-S Desipramine Dextrallorphan Dextromethorphan Dextrorphan Dimemorfan DMT Donepezil DTG Escitalopram Fluoxetine Fluvoxamine Heroin Ibogaine Igmesine Imipramine JO-1784 Ketamine L-687,384 Lamotrigine Lu 28-179 MDMA Memantine Metaphit Methamphetamine Methoxetamine Methylphenidate Morphine Naluzotan Noscapine OPC-14523 Opipramol PB-28 PD-144,415 Pentazocine Pentoxyverine Phencyclidine PRE-084 Pregnenolone Pregnenolone sulfate Quetiapine RTI-55 SA-4503 Siramesine Tapentadol Tenocyclidine Tramadol UMB23 UMB82 Venlafaxine

Antagonists	AC927 AHD1 AZ66 BD1008 BD1047 BD1060 BD1063 BD1067 BMY-14802 CM156 E-5842 Haloperidol Lamotrigine LR132 LR172 MIN-101 MS-377 Naloxone Naltrexone NE-100 Panamesine PD-144418 Progesterone Quingestrone Rimcazole S1RA (E-52862) Sertraline SM-21 SR-31742A UMB100 UMB101 UMB103 UMB116 YZ-011 YZ-069 YZ-185

Unknown / unsorted	4C-T-2 5-MeO-DiPT 18-MC β-Endopsychosin Chlorpromazine Clemastine Clocapramine Cloperastine D-Deprenyl DiPT DPT Gevotroline Nepinalone Selegiline TMA; Allosteric modulators: SKF-83959

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