Substituted phenylmorpholine

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Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.[1][2][3][4]

Various phenmetrazine derivatives
The 2S,3S isomer of phendimetrazine (i.e. (2S,3S)-3,4-dimethyl-2-phenylmorpholine)
The (+)-enantiomer & (−)-enantiomer of pseudophenmetrazine.
List of phenmetrazine analogues and related compounds
Substance Structure CAS number
2-phenylmorpholine 2-phenylmorpholine.svg 23972-41-0
2-phenyl-3-methylmorpholine (phenmetrazine) Phenmetrazine.svg 134-49-6
2-phenyl-3,4-dimethylmorpholine (phendimetrazine) Phendimetrazine.svg 634-03-7
2-phenyl-5-methylmorpholine (isophenmetrazine) Isophenmetrazine structure.png 80123-66-6
2-phenyl-3-ethylmorpholine (phenetrazine) Phenetrazine structure.png 100368-98-7
2-phenyl-3-methyl-4-ethylmorpholine (phenmetetrazine) Phenmetetrazine structure.png 92196-09-3
2-phenyl-3,5-dimethylmorpholine (PDM-35) 2-phenyl-3,5-dimethylmorpholine.png 1218345-44-8
2-phenyl-3,6-dimethylmorpholine (6-methylphenmetrazine, 3,6-DMPM) 2-phenyl-3,6-dimethylmorpholine structure.png 92902-99-3
2-phenyl-5,5-dimethylmorpholine (G-130) G-130 structure.png 42013-48-9
2-phenyl-3-methylmorpholin-5-one (fenmetramide) Fenmetramide.png 5588-29-4
4-isopropyl-2-phenylmorpholine[5] 4-Isopropyl-2-phenylmorpholine.png 23222-62-0
Fenbutrazate Fenbutrazate.png 4378-36-3
Morazone Morazone.png 6536-18-1
2-Fluorophenmetrazine 2-Fluorophenmetrazine structure.png 1533654-24-8
3-fluorophenmetrazine (PAL-593) 3-fluorophenmetrazine proper structure.svg 1350768-28-3
4-Fluorophenmetrazine (PAL-748) 4-Fluorophenmetrazine structure.png 1097796-73-0
3-fluorophenetrazine 3-Fluorophenetrazine structure.png
3-chlorophenmetrazine (PAL-594) 3-Chlorophenmetrazine structure.png 1097796-78-5
3-Methoxyphenmetrazine 3-MeO-phenmetrazine structure.png
2-Methylphenmetrazine 2-Methylphenmetrazine structure.png 1507705-48-7
3-methylphenmetrazine (PAL-773) 3-Methylphenmetrazine structure.png 1350768-41-0
4-methylphenmetrazine (PAL-747) 4-Methylphenmetrazine structure.png 1998216-41-3
4-methylphendimetrazine 4-Methylphendimetrazine structure.png 1445576-23-7
3,4-methylenedioxyphenmetrazine[6] MDPHMZ structure.png
Naphthylmetrazine (PAL-704) Naphthylmetrazine structure.png
2-(thiophen-2-yl)-3-methylmorpholine 2-Thiophenyl-3-methylmorpholine structure.png
2-(2,5-dimethoxy-4-bromophenyl)morpholine[7] 2CB-norphenmetrazine structure.png
2-(3-(Trifluoromethyl)phenyl)morpholine (flumexadol)[8] Flumexadol structure.svg 30914-89-7
Oxaflozane Oxaflozane.svg 26629-87-8
Phenmetrazol Phenmetrazol structure.png 1350768-19-2
N-Ethylphenmetrazol N-Ethylphenmetrazol structure.png 97630-98-3
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol (radafaxine) Radafaxine Structural Formulae.png 106083-71-0
(2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol (manifaxine) GW-320,659 structure.png 135306-39-7
PF-219,061[9] PF-219,061 Structural Formulae.png 710654-74-3
PF-592,379 PF-592379 structure.png 710655-15-5
OSU-6162 OSU-6162 structure.png 156907-84-5
2-Methyl-3-phenylpiperidine 2-Methyl-3-phenylpiperidine structure.png 70769-67-4
2-Phenyl-3-methyl-thiomorpholine 2-Phenyl-3-methyl-thiomorpholine structure.png
Picilorex Picilorex.svg 62510-56-9
Butyltolylquinuclidine Butyltolylquinuclidine structure.png
3-benzylmorpholine (3-BZM)[10] 3-benzylmorpholine.png 7684-27-7
3-Benzhydrylmorpholine (3-BZHM) 3-BZHM structure.png 93406-27-0

See also[edit]


  1. ^ Boswell GE (1997). "Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines". Journal of Heterocyclic Chemistry. 34 (6): 1813–1820. doi:10.1002/jhet.5570340629.
  2. ^ US 20130203752, Blough BE, Rothman R, Landavazo A, Page KM, Decker AM, "Phenylmorpholines and analogues thereof", published 8 August 2013 
  3. ^ Mayer FP, Burchardt NV, Decker AM, Partilla JS, Li Y, McLaughlin G, et al. (May 2018). "Fluorinated phenmetrazine "legal highs" act as substrates for high-affinity monoamine transporters of the SLC6 family". Neuropharmacology. 134 (Pt A): 149–157. doi:10.1016/j.neuropharm.2017.10.006. PMC 7294773. PMID 28988906.
  4. ^ McLaughlin G, Baumann MH, Kavanagh PV, Morris N, Power JD, Dowling G, et al. (September 2018). "Synthesis, analytical characterization, and monoamine transporter activity of the new psychoactive substance 4-methylphenmetrazine (4-MPM), with differentiation from its ortho- and meta- positional isomers". Drug Testing and Analysis. 10 (9): 1404–1416. doi:10.1002/dta.2396. PMC 7316143. PMID 29673128.
  5. ^ Chem-Sink (chemicals that are Sn2 products & Friedel-Crafts alkylation reactants)
  6. ^ Swist M, Wilamowski J, Zuba D, Kochana J, Parczewski A (May 2005). "Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA". Forensic Science International. 149 (2–3): 181–92. doi:10.1016/j.forsciint.2004.06.016. PMID 15749360.
  7. ^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–41. doi:10.1021/jm040082s. PMID 15537358.
  8. ^ Chemicalbook dot com: Flumexadol
  9. ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. 1st Page.
  10. ^ NIH PubChem Compound Summary for CID 3283983

External links[edit]