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Meciadanol

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Meciadanol
Names
Chemical structure of meciadanol
IUPAC name 3-Methoxyflavan-3′,4′,5,7-tetrol
Systematic IUPAC name (2R,3S)-2-(3,4-Dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol
Other names 3-O-Methylcatechin Meciadanolum 3',4',5,7-Tetrahydroxy-3-methoxyflavan (2R,3S)-2-(3,4-Dihydroxyphenyl)-3-methoxy-5,7-chromandiol
Identifiers
CAS Number	65350-86-9^Y
3D model (JSmol)	Interactive image
ChemSpider	8555738^N
ECHA InfoCard	100.059.719
PubChem CID	10380295
UNII	2H64SE2UXS^Y
CompTox Dashboard(EPA)	DTXSID201024352
InChI InChI=1S/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3/t15-,16+/m0/s1^N Key: PDHSAQOQVUXZGQ-JKSUJKDBSA-N^N InChI=1/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3/t15-,16+/m0/s1 Key: PDHSAQOQVUXZGQ-JKSUJKDBBQ
SMILES CO[C@H]1CC2=C(C=C(C=C2O[C@@H]1C3=CC(=C(C=C3)O)O)O)O
Properties
Chemical formula	C₁₆H₁₆O₆
Molar mass	304.298 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Meciadanol is a syntheticO-methylated flavanol. It is the 3-O-methylation ofcatechin.

It inhibitshistidine decarboxylase in rats.^[1]

References

[edit]

^Konturek, Stanislaw J; Ellen Kitler, Mary; Brzozowski, Tomasz; Radecki, Tadeusz (1986). "Gastric protection by meciadanol".Digestive Diseases and Sciences.31 (8):847–852.doi:10.1007/BF01296054.PMID 3525045.S2CID 11063794.

v t e Flavan-3-ols and theirglycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin Robinetinidol
O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A,B,C D Polydine ((+)-catechin 7-O-α-L-arabinoside) Symplocoside (3'-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products:L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR):Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors:Non-selective:Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors:MAO-A-selective:Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g.,harmine,harmaline,harman,norharman,tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors:MAO-B selective:Adarigiline Almoxatone D-Deprenyl Desmethylselegiline Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline Tisolagiline Vafidemstat

Phenethylamines
(dopamine,epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products:Phenylalanine→Tyrosine Inhibitors:3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products:Tyrosine→L-DOPA (levodopa) Inhibitors:2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products:Dopamine→Norepinephrine (Noradrenaline) Inhibitors:Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products:Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors:CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products:Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors:2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin,melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products:Tryptophan→5-HTP Inhibitors:AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products:Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products:N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products:L-Histidine→Histamine Inhibitors:Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products:Histamine→N-Methylhistamine Inhibitors:Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products:Histamine→Imidazole acetic acid Inhibitors:Pimagedine (aminoguanidine)

See also:Receptor/signaling modulators •Adrenergics •Dopaminergics •Melatonergics •Serotonergics •Monoamine reuptake inhibitors •Monoamine releasing agents •Monoamine neurotoxins

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