Substituted phenylmorpholines, orsubstituted phenmetrazines alternatively, arechemical derivatives of2-phenylmorpholine or of thepsychostimulantdrugphenmetrazine.
Most such compounds act asreleasers of monoamine neurotransmitters, and havestimulant effects. Some also act as agonists atserotonin receptors, and compounds with an N-propyl substitution act asdopamine receptor agonists.
A number of derivatives from this class have been investigated for medical applications, such as for use asanorectics or medications for the treatment ofADHD. Some compounds have also become subject to illicit use asdesigner drugs.[1][2][3][4]
| Substance | Structure | CAS # |
|---|---|---|
| 2-phenylmorpholine |  | 23972-41-0 |
| 2-phenyl-3-methylmorpholine (phenmetrazine) |  | 134-49-6 |
| 2-phenyl-3,4-dimethylmorpholine (phendimetrazine) |  | 634-03-7 |
| 2-phenyl-5-methylmorpholine (isophenmetrazine) |  | 80123-66-6 |
| 2-phenyl-3-ethylmorpholine (phenetrazine) |  | 100368-98-7 |
| 2-phenyl-3-methyl-4-ethylmorpholine (phenmetetrazine) |  | 92196-09-3 |
| 2-phenyl-3,5-dimethylmorpholine (PDM-35) |  | 1218345-44-8 |
| 2-phenyl-3,6-dimethylmorpholine (6-methylphenmetrazine, 3,6-DMPM) |  | 92902-99-3 |
| 2-phenyl-5,5-dimethylmorpholine (G-130) |  | 42013-48-9 |
| 2-phenyl-3-methylmorpholin-5-one (fenmetramide) |  | 5588-29-4 |
| 4-isopropyl-2-phenylmorpholine[5] |  | 23222-62-0 |
| Fenbutrazate |  | 4378-36-3 |
| Morazone |  | 6536-18-1 |
| 2-Fluorophenmetrazine |  | 1533654-24-8 |
| 3-fluorophenmetrazine (PAL-593) |  | 1350768-28-3 |
| 4-Fluorophenmetrazine (PAL-748) |  | 1097796-73-0 |
| 3-fluorophenetrazine |  | |
| 3-chlorophenmetrazine (PAL-594) |  | 1097796-78-5 |
| 3-Methoxyphenmetrazine |  | |
| 2-Methylphenmetrazine |  | 1507705-48-7 |
| 3-methylphenmetrazine (PAL-773) |  | 1350768-41-0 |
| 4-methylphenmetrazine (PAL-747) |  | 1998216-41-3 |
| 4-methylphendimetrazine |  | 1445576-23-7 |
| 3-Iodophenmetrazine | ||
| 2-(4-Bromo-2,5-dimethoxyphenyl)morpholine (2C-B-morpholine) |  | |
| 3,4-Methylenedioxyphenmetrazine[6] |  | |
| Naphthylmetrazine (PAL-704) |  | |
| 2-(thiophen-2-yl)-3-methylmorpholine |  | |
| 2-(3-(Trifluoromethyl)phenyl)morpholine (flumexadol)[7] |  | 30914-89-7 |
| Oxaflozane |  | 26629-87-8 |
| Phenmetrazol |  | 1350768-19-2 |
| N-Ethylphenmetrazol |  | 97630-98-3 |
| (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol (radafaxine) |  | 106083-71-0 |
| (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol (manifaxine) |  | 135306-39-7 |
| PF-219,061[8] |  | 710654-74-3 |
| PF-592,379 |  | 710655-15-5 |
| OSU-6162 |  | 156907-84-5 |
| LPH-5[9] |  | 2641630-97-7 |
| 2-Methyl-3-phenylpiperidine |  | 70769-67-4 |
| 2-Phenyl-3-methyl-thiomorpholine |  | |
| 4-Methyl-5-phenyl-1,3-oxazolidine[10] |  | 42794-92-3 |
| Picilorex |  | 62510-56-9 |
| Butyltolylquinuclidine |  | |
| 3-benzylmorpholine (3-BZM)[11] |  | 7684-27-7 |
| 3-Benzhydrylmorpholine (3-BZHM) |  | 93406-27-0 |
Additional phenylmorpholines and their activities asmonoamine releasing agents (MRAs) have been described.[12]
[...] Table 3. Monoamine Release and 5HT2B Activity of a Series of Phenmetrazine Analogs [...] Table 4. Comparison of the DA, 5-HT, and NE Releasing Activity of a Series of Phenmetrazine Analogs [...] Table 5. Comparison of the DA, 5-HT, and NE Releasing Activity of a Series of (2S,5S)-5-methyl-2-phenylmorpolines
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