Substituted phenylmorpholine explained

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]}

List of phenmetrazine analogues and related compounds! Substance! Structure! CAS number

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
		4378-36-3
		6536-18-1
2-Fluorophenmetrazine		1533654-24-8
3-fluorophenmetrazine (PAL-593)		1350768-28-3
4-Fluorophenmetrazine (PAL-748)		1097796-73-0
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
		1445576-23-7
3,4-Methylenedioxyphenmetrazine^[6]
Naphthylmetrazine (PAL-704)
2-(thiophen-2-yl)-3-methylmorpholine
2-(2,5-dimethoxy-4-bromophenyl)morpholine^[7]
2-(3-(Trifluoromethyl)phenyl)morpholine (flumexadol)^[8]		30914-89-7
		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^[9]		710654-74-3
		710655-15-5
		156907-84-5
LPH-5^[10]		2641630-97-7
2-Methyl-3-phenylpiperidine		70769-67-4
2-Phenyl-3-methyl-thiomorpholine
		62510-56-9
3-benzylmorpholine (3-BZM)^[11]		7684-27-7
3-Benzhydrylmorpholine (3-BZHM)		93406-27-0

See also

• Substituted amphetamine
• Substituted benzofuran
• Substituted cathinone
• Substituted methylenedioxyphenethylamine
• List of aminorex analogues
• List of methylphenidate analogues
• List of phenyltropanes
• List of cocaine analogues

Notes and References

1. 10.1002/jhet.5570340629 . 34 . Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines . 1997 . Journal of Heterocyclic Chemistry . 1813–1820 . Boswell GE . 6 . free .
2. US . 20130203752 . Phenylmorpholines and analogues thereof . 8 August 2013 . Blough BE, Rothman R, Landavazo A, Page KM, Decker AM .
3. Mayer FP, Burchardt NV, Decker AM, Partilla JS, Li Y, McLaughlin G, Kavanagh PV, Sandtner W, Blough BE, Brandt SD, Baumann MH, Sitte HH . 6 . Fluorinated phenmetrazine "legal highs" act as substrates for high-affinity monoamine transporters of the SLC6 family . Neuropharmacology . 134 . Pt A . 149–157 . May 2018 . 28988906 . 10.1016/j.neuropharm.2017.10.006 . 7294773 . free .
4. McLaughlin G, Baumann MH, Kavanagh PV, Morris N, Power JD, Dowling G, Twamley B, O'Brien J, Hessman G, Westphal F, Walther D, Brandt SD . 6 . 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 . September 2018 . 29673128 . 10.1002/dta.2396 . 7316143 .
5. http://www.chemsink.com/compound/6430939/ Chem-Sink (chemicals that are Sn2 products & Friedel-Crafts alkylation reactants)
6. Swist 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 . 149 . 2–3 . 181–92 . May 2005 . 15749360 . 10.1016/j.forsciint.2004.06.016 .
7. Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA . 6 . 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 . November 2004 . 15537358 . 10.1021/jm040082s .
8. http://www.chemicalbook.com/ChemicalProductProperty_EN_CB51178778.htm Chemicalbook dot com: Flumexadol
9. http://www.faqs.org/patents/imgfull/20090318451_01 Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. 1st Page.
10. https://patentimages.storage.googleapis.com/a2/12/19/8424e3822cbe82/US20210137908A1.pdf Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908
11. https://pubchem.ncbi.nlm.nih.gov/compound/3-benzylmorpholine NIH PubChem Compound Summary for CID 3283983