Substituted phenylmorpholine

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Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine.

Various phenmetrazine derivatives
The 2S,3S isomer of phendimetrazine (i.e. (2S,3S)-3,4-dimethyl-2-phenylmorpholine)
The (+)-enantiomer & (−)-enantiomer of pseudophenmetrazine.
c.f. the phenyltropane class of compounds when the tropane is drawn in a manner resembling other than the boat formation.
Phenmetrazine analogues or substituted phenmetrazines,
acting as transporter releasing agents of dopamine and noradrenaline, as well as serotonin receptor agonists, also including the similar "phenylmorpholine"[1] class
Substance Structure
2-phenylmorpholine 2-phenylmorpholine.svg
2-phenyl-3-methylmorpholine (phenmetrazine) Phenmetrazine.svg
2-phenyl-3,4-dimethylmorpholine (phendimetrazine) Phendimetrazine.svg
2-phenyl-3,5-dimethylmorpholine (PDM-35) 2-phenyl-3,5-dimethylmorpholine.jpg
2-phenyl-3,6-dimethylmorpholine (6-methylphenmetrazine, 3,6-DMPM) 2-phenyl-3,6-dimethylmorpholine structure.png
2-phenyl-5,5-dimethylmorpholine (G-130) G-130 structure.png
2-phenyl-3-methylmorpholin-5-one (fenmetramide) Fenmetramide.png
4-isopropyl-2-phenylmorpholine[2] 4-Isopropyl-2-phenylmorpholine.jpg
3-methyl-4-nitroso-2-phenyl-morpholine[3] 3-methyl-4-nitroso-2-phenyl-morpholine.jpg
3-fluorophenmetrazine 3-fluorophenmetrazine proper structure.png
3,4-methylenedioxyphenmetrazine[4] MDPHMZ structure.png
2-(2,5-dimethoxy-4-bromophenyl)morpholine[5] 2CB-norphenmetrazine structure.png
2-(3-(Trifluoromethyl)phenyl)morpholine (flumexadol)[6] Flumexadol structure.svg
Oxaflozane Oxaflozane.svg
3-benzylmorpholine (3-BZM)[7] 3-benzylmorpholine.jpg
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol (radafaxine) Radafaxine Structural Formulae.png
(2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol (manifaxine) GW-320,659 structure.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.
Substituted phenmetrazine 'dopaminergic nociceptives'
i.e. "dopamine-receptor direct agonists"
Substance Structure
PF-219,061 PF-219,061 Structural Formulae.png
PF-592,379 PF-592379 structure.png
OSU-6162 OSU-6162 structure.png
4-(4-propylmorpholin-2-yl)phenol[9] 4-(4-propylmorpholin-2-yl)phenol.jpg
2-hydroxy-5-(4-propylmorpholin-2-yl)benzamide[10] 2-hydroxy-5-(4-propylmorpholin-2-yl)benzamide.jpg
(5S)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholin-2-ol[11] (5S)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholin-2-ol.jpg
2-ethyl-6-(3-methoxy-phenyl)-4-propyl-morpholin-3-one[12] 2-ethyl-6-(3-methoxy-phenyl)-4-propyl-morpholin-3-one.jpg

See also

3-Benzhydrylmorpholine, a stimulant which is effectively an intermediate analog of the pipradrol class and phenmetrazine.

References

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  1. ↑ Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines DOI: 10.1002/jhet.5570340629
  2. ↑ Chem-Sink (chemicals that are Sn2 products & Friedel-Crafts alkylation reactants)
  3. ↑ ChemIndustry.com: 3-methyl-4-nitroso-2-phenyl-morpholine
  4. ↑ 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
  5. ↑ 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
  6. ↑ Chemicalbook dot com: Flumexadol
  7. ↑ [pubchem.ncbi.nlm.nih.gov/compound/3-benzylmorpholine NIH PubChem Compound Summary for CID 3283983]
  8. ↑ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. 1st Page.
  9. ↑ 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
  10. ↑ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 48
  11. ↑ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 58
  12. ↑ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. Example 45
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