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Miotine

First synthetic carbamate to find clinical application due to its miotic activity. Eye drop. The hydrochlorid is cid=46092. IC50 hAChE 0.1 microM; IC50 hAChE 0.406 microM

General

Type : Carbamate, Derivative of Rivastigmine

Chemical_Nomenclature : [3-(1-dimethylaminoethyl)phenyl] methylaminoformate

Canonical SMILES : CC(C1=CC(=CC=C1)OC(=O)NC)[NH+](C)C.[Cl-] || CC(C1=CC(=CC=C1)OC(=O)NC)N(C)C

InChI : InChI=1S\/C12H18N2O2.ClH\/c1-9(14(3)4)10-6-5-7-11(8-10)16-12(15)13-2\;\/h5-9H,1-4H3,(H,13,15)\;1H || InChI=1S\/C12H18N2O2\/c1-9(14(3)4)10-6-5-7-11(8-10)16-12(15)13-2\/h5-9H,1-4H3,(H,13,15)

InChIKey : SXVZMCIGRIYWTD-UHFFFAOYSA-N || KQOUPMYYRQWZLI-UHFFFAOYSA-N

Other name(s) : AR-28  ||  T-1843  ||  Methylcarbamic ester of alpha-3-hydroxyphenylethyldimethylamine hydrochloride  ||  Carbamic acid, N-methyl-, 3-(alpha-dimethylaminoethyl)phenyl ester, hydrochloride  ||  Carbamic acid, N-methyl-, m-(alpha-dimethylaminoethyl)phenyl ester, hydrochloride  ||  63982-32-1  ||  C11763

MW : 222.284

Formula : C12H18N2O2

CAS_number :

PubChem : 46093,    46092

UniChem : SXVZMCIGRIYWTD-UHFFFAOYSA-N,    KQOUPMYYRQWZLI-UHFFFAOYSA-N

Wikipedia : Miotine

Target

Families : Miotine ligand of proteins in family
ACHE

References (6)

Title : Design, synthesis, and biological evaluation of conformationally restricted rivastigmine analogues - Bolognesi_2004_J.Med.Chem_47_5945
Author(s) : Bolognesi ML , Bartolini M , Cavalli A , Andrisano V , Rosini M , Minarini A , Melchiorre C
Ref : Journal of Medicinal Chemistry , 47 :5945 , 2004
Abstract :
PubMedSearch : Bolognesi_2004_J.Med.Chem_47_5945
PubMedID: 15537349

Title : Investigations on the influence of chemical constitution upon toxicity\; compounds related to miotine -
Author(s) : Davies RE , Haworth RD , Jones B , Lamberton AH
Ref : J Chem Soc , :191 , 1947
PubMedID: 20238647

Title : Studies on the relationship between chemical constitution and physiological action: Molecular dissymmetry and physiological activity. -
Author(s) : Easson LH , Stedman E
Ref : Biochemical Journal , 27 :1257 , 1933
PubMedID: 16745220

Title : Studies on the relationship between chemical constitution and physiological action: The inhibitory action of certain synthetic urethanes on the activity of liver esterase. -
Author(s) : Stedman E
Ref : Biochemical Journal , 25 :1147 , 1931
PubMedID: 16744678

Title : Chemical constitution and miotic action -
Author(s) : Stedman E
Ref : American Journal of Physiology , 90 :528 , 1929
PubMedID:

Title : Studies on the relationship between chemical constitution and physiological action: Part II. The miotic activity of urethanes derived from the isomeric hydroxybenzyldimethylamines. -
Author(s) : Stedman E
Ref : Biochemical Journal , 23 :17 , 1929
PubMedID: 16744184