2-Methoxyethyl-18-methoxycoronaridinate
2-Methoxyethyl-18-methoxycoronaridinate
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| Identifiers |
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| PubChem (CID) |
10070278 |
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| ChemSpider |
9212214  Y |
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| Chemical and physical data |
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| Formula |
C24H32N2O4 |
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| Molar mass |
412.521 g/mol |
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| 3D model (Jmol) |
Interactive image |
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COCCOC(=O)C12CC(C4)CN(C2C4CCOC)CCc5c1nc3ccccc35
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InChI=1S/C24H32N2O4/c1-28-10-8-17-13-16-14-24(23(27)30-12-11-29-2)21-19(7-9-26(15-16)22(17)24)18-5-3-4-6-20(18)25-21/h3-6,16-17,22,25H,7-15H2,1-2H3/t16-,17+,22+,24-/m1/s1 YKey:OLFXZBDPKBSIPG-JIQZGXBJSA-N Y
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(–)-2-Methoxyethyl-18-methoxycoronaridinate (ME-18-MC) is a second generation synthetic derivative of ibogaine developed by the research team led by the pharmacologist Stanley D. Glick from the Albany Medical College and the chemist Martin E. Kuehne from the University of Vermont.[1] In animal studies it has shown similar efficacy to the related compound 18-methoxycoronaridine (18-MC) at reducing self-administration of morphine and methamphetamine but with higher potency by weight, showing anti-addictive effects at the equivalent of half the minimum effective dose of 18-MC. Similarly to 18-MC itself, ME-18-MC acts primarily as a selective α3β4 nicotinic acetylcholine antagonist, although it has a slightly stronger effect than 18-MC as an NMDA antagonist, and its effects on opioid receptors are weaker than those of 18-MC at all except the kappa opioid receptor, at which it has slightly higher affinity than 18-MC.[2][3]
See also
References
- ↑ Stanley D. Glick, Martin E. Kuehne. Ibogamine congeners. US Patent 6211360
- ↑ Kuehne, ME; He, L; Jokiel, PA; Pace, CJ; Fleck, MW; Maisonneuve, IM; Glick, SD; Bidlack, JM (2003). "Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents". Journal of Medicinal Chemistry. 46 (13): 2716–30. doi:10.1021/jm020562o. PMID 12801235.
- ↑ Pace, CJ; Glick, SD; Maisonneuve, IM; He, LW; Jokiel, PA; Kuehne, ME; Fleck, MW (2004). "Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration". European Journal of Pharmacology. 492 (2–3): 159–67. doi:10.1016/j.ejphar.2004.03.062. PMID 15178360.
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| | mACh |
- Antagonists: 3-Quinuclidinyl benzilate
- 4-DAMP
- Aclidinium bromide
- Anisodamine
- Anisodine
- Antihistamines (first-generation) (e.g., brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine (pyrilamine), phenindamine, pheniramine, promethazine, tripelennamine, triprolidine)
- Atropine
- Atropine methonitrate
- Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, zotepine)
- Benactyzine
- Benzatropine (benztropine)
- Benzilylcholine mustard
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Caramiphen
- Cloperastine
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine (dicycloverine)
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine (ethybenztropine)
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba toxin 3
- Mamba toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-piperidyl benzilate
- N-Methyl-3-piperidyl benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pipenzolate bromide
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- Revefenacin
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine (hyoscine)
- Sofpironium bromide
- Solifenacin
- Telenzepine
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
- Timepidium bromide
- Tiotropium bromide
- Tolterodine
- Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nortriptyline, protriptyline, trimipramine)
- Trihexyphenidyl
- Tripitamine
- Tropacine
- Tropatepine
- Tropicamide
- Typical antipsychotics (e.g., chlorpromazine, loxapine, thioridazine)
- WIN-2299
- Xanomeline
- Zamifenacin
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| | nACh |
- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Ivermectin
- Levamisole
- Lobeline
- MEM-63,908 (RG-3487)
- Morantel
- Nicotine (tobacco)
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- SB-206553
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberyldicholine
- Suxamethonium (succinylcholine)
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
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| | ChAT |
- Inhibitors: 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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| | AChE | |
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| | BChE |
- Inhibitors: Cymserine
- Many of the AChE inhibitors listed above
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