Substituted phenylmorpholine Class of chemical compounds
Various phenmetrazine derivatives Substituted phenylmorpholines , or substituted phenmetrazines alternatively, are chemical derivatives of 2-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 phenylmorpholines
Additional phenylmorpholines and their activities as monoamine releasing agents (MRAs) have been described.[ 12]
See also
References
^ 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 ^ US 20130203752 , Blough BE, Rothman R, Landavazo A, Page KM, Decker AM, "Phenylmorpholines and analogues thereof", published 8 August 2013 ^ 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 . ^ 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 . ^ Chem-Sink (chemicals that are Sn2 products & Friedel-Crafts alkylation reactants) ^ 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 . ^ 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 . ^ Chemicalbook dot com: Flumexadol ^ Morpholine Dopamine Agonists For The Treatment Of Pain. Michael Andrew Ackley US 2009/0318451 AI Dec., 24th 2009. 1st Page. ^ Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908 ^ NIH PubChem Compound Summary for CID 3283983 ^ "Phenylmorpholines and analogues thereof" . Google Patents . 20 May 2011. Retrieved 7 December 2024 . [...] 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
External links
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , bromojimscaline , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CJP 2CLisaB 2CLisaH 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , 3-PPP , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 , Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tolazoline Tricyclics (e.g., AMDA , AMDH , benzoctamine , dizocilpine , SpAMDA )ZC-B
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
