Meciadanol

Meciadanol
Names

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
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 their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Meciadanol is a synthetic O-methylated flavanol. It is the 3-O-methylation of catechin.

It inhibits histidine decarboxylase in rats.^[1]

References

^ 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.

Flavan-3-ols and their glycosides

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

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 Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
DBHTooltip Dopamine beta-monooxygenase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone
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 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