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Adafenoxate
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Names
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Preferred IUPAC name
2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate
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Identifiers
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ChEMBL
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ChemSpider
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UNII
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InChI=1S/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2 YKey: PLSMXIQMWYSHIV-UHFFFAOYSA-N YInChI=1/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2 Key: PLSMXIQMWYSHIV-UHFFFAOYAK
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Clc4ccc(cc4)OCC(=O)OCCNC12CC3CC(C1)CC(C2)C3
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Properties
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C20H26ClNO3
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Molar mass
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363.87834 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is Y N ?)
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Infobox references
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Tracking categories (test):
Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.[1]
Synthesis
Ex 1: 4-Chlorophenoxyacetic acid (pCPA) [122-88-3] is converted to its acid chloride to give 4-chlorophenoxyacetyl chloride [4122-68-3] (1). Esterification with 2-(1-adamantylamino)ethanol [3716-66-3] (2) gives Adafenoxate (3) in a single step.
Ex 2: Same as above but Fischer–Speier esterification done via a DS-trap. This gives an 88% yield.
References
- ↑ "A study of nootropic drugs for anti-anxiety action". Acta Physiol Pharmacol Bulg 13 (4): 25–30. 1987. PMID 2896427.
- ↑ Romeo R. Andreoli, Xavier D. Cirera, U.S. Patent 4,476,319 (1984 to Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A.).
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mAChRs | Agonists | |
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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, [[Chemistry:Dimetdimetindene, Diphenhydramine|diphenhydramine]], doxylamine, meclizine, mepyramine (pyrilamine), mequitazine, perlapine, phenindamine, pheniramine, Phenyltoloxamine|Phenyltoloxamine]]]], promethazine, propiomazine, triprolidine)
- AQ-RA 741
- Atropine
- Atropine methonitrate
- Atypical antipsychotics (e.g., clozapine, Chemistry:Fluperlapine
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Precursors (and prodrugs) | |
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nAChRs | Agonists (and PAMs) |
- 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
- Bephenium hydroxynaphthoate
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol (alcohol)
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Ivermectin
- JNJ-39393406
- 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
- Pyrantel
- Rivanicline
- RJR-2429
- Sazetidine A
- SB-206553
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberyldicholine
- Suxamethonium (succinylcholine)
- Suxethonium (succinyldicholine)
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tribendimidine
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
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Antagonists (and NAMs) | |
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Precursors (and prodrugs) | |
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 | Original source: https://en.wikipedia.org/wiki/Adafenoxate. Read more |