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A115

Supelco

Amitriptyline metabolite, (±)-E-10-hydroxylated-

analytical standard

Synonym(s):

(±)-(E)-5-[3-(Dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol

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About This Item

Empirical Formula (Hill Notation):
C20H23NO
CAS Number:
64520-05-4
Molecular Weight:
293.40
MDL number:
MFCD00069200
UNSPSC Code:
41116107
PubChem Substance ID:
329770681
NACRES:
NA.24

grade

analytical standard

Quality Level

200

form

solid

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

mp

97-99 °C

solubility

0.1 M HCl: soluble
H2O: insoluble
methanol: soluble

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

SMILES string

CN(C)CC\C=C1/c2ccccc2CC(O)c3ccccc13

InChI

1S/C20H23NO/c1-21(2)13-7-12-17-16-9-4-3-8-15(16)14-20(22)19-11-6-5-10-18(17)19/h3-6,8-12,20,22H,7,13-14H2,1-2H3/b17-12+

InChI key

GHWBJXOKAFHZAI-SFQUDFHCSA-N

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Metabolite of amitriptyline, tricyclic antidepressant; chromatographic standard.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
FN10182301
FN06022219
FN04232005
FN04301906
FN12191701

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X Zhang
Zhonghua shen jing jing shen ke za zhi = Chinese journal of neurology and psychiatry, 25(4), 196-198 (1992-08-01)
The serum concentrations of amitriptyline and its 3 metabolites--nortriptyline, 10-hydroxy-amitriptyline and 10-hydroxy-nortriptyline were determined in 18 depressive patients treated with amitriptyline for 6 weeks. The relationships between the serum concentrations and the clinical effects were statistically analyzed and showed significant
U Breyer-Pfaff et al.
Clinical pharmacology and therapeutics, 52(4), 350-358 (1992-10-01)
In 26 hospitalized patients with depression, a combined pharmacogenetic test with dextromethorphan, a substrate of cytochrome P450IID6, and mephenytoin, the S-form of which is hydroxylated by a P450IIC isozyme, was carried out before amitriptyline therapy. Metabolites were determined in 24-hour
F Coudoré et al.
Fundamental & clinical pharmacology, 8(6), 525-531 (1994-01-01)
Kinetics of amitriptyline (AMI), its demethylated metabolites nortriptyline (NOR) and demethylnortriptyline (DM-NOR), and its hydroxylated metabolites, the E and Z isomers or 10-hydroxy-amitriptyline (E- and Z-10-OH-AMI) and of 10-hydroxynortriptyline (E- and Z-10-OH-NOR) were studied in plasma and brain from Swiss
R T Coutts et al.
Xenobiotica; the fate of foreign compounds in biological systems, 27(1), 33-47 (1997-01-01)
1. Expressed human cytochrome P450 enzyme CPY2D6 was used to metabolize amitriptyline (AMI). It was established that CYP2D6 not only catalyzed ring 10-hydroxylation of AMI, but also mediated its N-demethylation to nortriptyline (NT), as well as the formation of 10-hydroxy-NT
E Nusser et al.
Journal of chromatography, 528(1), 163-171 (1990-06-08)
E- and Z-10-hydroxyamitriptyline (E- and Z-10-OH-AT) are racemic alcoholic metabolites of the antidepressant amitriptyline. Their enantiomers were separated by high-performance liquid chromatography as diastereomeric derivatives using R-(+)-alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride (Mosher's reagent). Although E-10-hydroxyamitriptyline excreted in patient urine in free form or
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