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Amiflamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Amiflamine
Clinical data
Other names(+)-4-(dimethylamino)-α,2-dimethylphenethylamine
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 4-[(2S)-2-Aminopropyl]-N,N,3-trimethylaniline
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H20N2
Molar mass192.306 g·mol−1
3D model (JSmol)
  • N(c1cc(c(cc1)C[C@@H](N)C)C)(C)C
  • InChI=1S/C12H20N2/c1-9-7-12(14(3)4)6-5-11(9)8-10(2)13/h5-7,10H,8,13H2,1-4H3/t10-/m0/s1 checkY
  • Key:HFQMYSHATTXRTC-JTQLQIEISA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amiflamine (FLA-336) is areversible inhibitor ofmonoamine oxidase A (MAO-A), thereby being aRIMA, and, to a lesser extent,semicarbazide-sensitive amine oxidase (SSAO), as well as aserotonin releasing agent (SRA).[1][2][3][4] It is aderivative of thephenethylamine andamphetaminechemical classes.[1] The (+)-enantiomer is the activestereoisomer.[2]

Amiflamine shows preference for inhibiting MAO-A inserotonergic relative tonoradrenergic anddopaminergicneurons.[5][6] In other words, at low doses, it can be used to selectively inhibit MAO-A enzymes in serotonin cells, whereas at higher doses it loses its selectivity.[5][6] This property is attributed to amiflamine's higheraffinity for theserotonin transporter over thenorepinephrine anddopamine transporters, as transporter-mediated carriage is required for amiflamine to enter monoaminergic neurons.[6]

See also

[edit]

References

[edit]
  1. ^abAsk AL, Högberg K, Schmidt L, Kiessling H, Ross SB (April 1982). "(+)-4-Dimethylamino-2,alpha-dimethylphenethylamine (FLA 336(+)), a selective inhibitor of the A form of monoamine oxidase in the rat brain".Biochemical Pharmacology.31 (7):1401–6.doi:10.1016/0006-2952(82)90035-1.PMID 7092929.
  2. ^abFowler CJ, Eriksson M, Thorell G, Magnusson O (October 1984). "Stereoselective inhibition of monoamine oxidase and semicarbazide-sensitive amine oxidase by 4-dimethylamino-2,alpha-dimethylphenethylamine (FLA 336)".Naunyn-Schmiedeberg's Archives of Pharmacology.327 (4):279–84.doi:10.1007/bf00506237.PMID 6514012.S2CID 25342831.
  3. ^Morikawa F, Ueda T, Arai Y, Kinemuchi H (1986). "Inhibition of monoamine oxidase A-form and semicarbazide-sensitive amine oxidase by selective and reversible monoamine oxidase-A inhibitors, amiflamine and FLA 788(+)".Pharmacology.32 (1):38–45.doi:10.1159/000138150.PMID 3945672.
  4. ^Ask AL, Fagervall I, Huang RB, Ross SB (June 1989). "Release of 3H-5-hydroxytryptamine by amiflamine and related phenylalkylamines from rat occipital cortex slices".Naunyn-Schmiedeberg's Archives of Pharmacology.339 (6):684–9.doi:10.1007/bf00168662.PMID 2770890.S2CID 21817180.
  5. ^abFowler CJ, Magnusson O, Ross SB (1984). "Intra- and extraneuronal monoamine oxidase".Blood Vessels.21 (3):126–31.doi:10.1159/000158505.PMID 6202347.
  6. ^abcAsk AL, Fagervall I, Ross SB (September 1983). "Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain".Naunyn-Schmiedeberg's Archives of Pharmacology.324 (2):79–87.doi:10.1007/BF00497011.PMID 6646243.S2CID 403633.
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
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