Substituted phenylmorpholine
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Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine.
![](http://web.archive.org./web/20170208154719im_/https://upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Pseudophenmetrazine.svg/300px-Pseudophenmetrazine.svg.png)
The (+)-enantiomer & (−)-enantiomer of pseudophenmetrazine.
![](http://web.archive.org./web/20170208154719im_/https://upload.wikimedia.org/wikipedia/commons/thumb/7/77/RTI112.png/300px-RTI112.png)
c.f. the phenyltropane class of compounds when the tropane is drawn in a manner resembling other than the boat formation.
Substance | Structure |
---|---|
2-phenylmorpholine | ![]() |
2-phenyl-3-methylmorpholine (phenmetrazine) | ![]() |
2-phenyl-3,4-dimethylmorpholine (phendimetrazine) | ![]() |
2-phenyl-3,5-dimethylmorpholine (PDM-35) | ![]() |
2-phenyl-3,6-dimethylmorpholine (6-methylphenmetrazine, 3,6-DMPM) | ![]() |
2-phenyl-5,5-dimethylmorpholine (G-130) | ![]() |
2-phenyl-3-methylmorpholin-5-one (fenmetramide) | ![]() |
4-isopropyl-2-phenylmorpholine[2] | ![]() |
3-methyl-4-nitroso-2-phenyl-morpholine[3] | ![]() |
3-fluorophenmetrazine | ![]() |
3,4-methylenedioxyphenmetrazine[4] | ![]() |
2-(2,5-dimethoxy-4-bromophenyl)morpholine[5] | ![]() |
2-(3-(Trifluoromethyl)phenyl)morpholine (flumexadol)[6] | ![]() |
Oxaflozane | ![]() |
3-benzylmorpholine (3-BZM)[7] | ![]() |
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol (radafaxine) | ![]() |
(2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol (manifaxine) | ![]() |
![](http://web.archive.org./web/20170208154719im_/https://upload.wikimedia.org/wikipedia/commons/5/5e/Nociceptive_morpholine_dopamine_agonist.png)
Nociceptive morpholine dopamine agonist substitution structure.[8] The cyclohexane, at where the oxygen leads to the phenyl (in-between the one and two positions on the cyclohexane itself, not the bridge of the phenyl) also have variants in this class being either a shaded or wedged bond at said oxygen. This class, however, possesses an ubiquitous propyl "tail" on the cyclohexane nitrogen compared to the DRA phenmetrazine analogue category proper.
Substance | Structure |
---|---|
PF-219,061 | ![]() |
PF-592,379 | ![]() |
OSU-6162 | ![]() |
4-(4-propylmorpholin-2-yl)phenol[9] | ![]() |
2-hydroxy-5-(4-propylmorpholin-2-yl)benzamide[10] | ![]() |
(5S)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholin-2-ol[11] | ![]() |
2-ethyl-6-(3-methoxy-phenyl)-4-propyl-morpholin-3-one[12] | ![]() |
See also[edit]
![](http://web.archive.org./web/20170208154719im_/https://upload.wikimedia.org/wikipedia/commons/thumb/a/a4/3-BZHM_structure.png/220px-3-BZHM_structure.png)
3-Benzhydrylmorpholine, a stimulant which is effectively an intermediate analog of the pipradrol class and phenmetrazine.
- Substituted phenethylamine
- Substituted amphetamine
- Substituted cathinone
- List of methylphenidate analogues
- List of phenyltropanes
- List of cocaine analogues
References[edit]
- ^ Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines DOI: 10.1002/jhet.5570340629
- ^ Chem-Sink (chemicals that are Sn2 products & Friedel-Crafts alkylation reactants)
- ^ ChemIndustry.com: 3-methyl-4-nitroso-2-phenyl-morpholine
- ^ Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A. Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA. Forensic Science International 10 May 2005, 149(2–3): 181–192. doi: 10.1016/j.forsciint.2004.06.016
- ^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA. Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J Med Chem. 2004 Nov 18;47(24):6034-41. PMID 15537358
- ^ Chemicalbook dot com: Flumexadol
- ^ NIH PubChem Compound Summary for CID 3283983
- ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. 1st Page.
- ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Pg. 25. Example 29 #414 diagram, schematic, and image 26
- ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 48
- ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 58
- ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 45