cis-10-hydroxy amitriptyline
cis-10-Hydroxy amitriptyline is a stereospecific oxidation derivative of amitriptyline, featuring a hydroxyl group at the 10th carbon of the indane ring in the cis configuration relative to the adjacent methylene bridge. This hydroxylation introduces a chiral center, altering the molecule's steric and electronic properties compared to the parent tricyclic antidepressant. The compound retains the core 10H-phenothiazine-like scaffold with a dimethylamino substituent on the aliphatic sidechain. It arises as a degradation byproduct under oxidative stress conditions and serves as a critical HPLC reference standard for quantifying amitriptyline stability profiles in pharmaceutical formulations.
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Molecular Formula
C20H23NO
Molecular Weight
293.4000
CAS Number
72402-20-1
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PubChem CID
6420900 ↗
IUPAC Name
(2Z)-2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol
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📝 Synonyms
(Z)-10-Hydroxyamitriptyline
Z-10-Hydroxyamitriptyline
72402-20-1
5H-Dibenzo(a,d)cyclohepten-10-ol, 5-(3-(dimethylamino)propylidene)-10,11-dihydro-, (Z)-
V05NFJ590Z
10-Hydroxyamitriptyline, (Z)-
DTXSID10873787
RefChem:907909
DTXCID001012004
(2Z)-2-[3-(dimethylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol
🔬 Chemical Identifiers
CN(C)CC/C=C\1/C2=CC=CC=C2CC(C3=CC=CC=C31)O
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-
GHWBJXOKAFHZAI-ATVHPVEESA-N
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