(E)-10-Hydroxyamitriptyline

Base Information

• Chemical Name: (E)-10-Hydroxyamitriptyline
• CAS No.: 64520-05-4
• Molecular Formula: C20H23 N O
• Molecular Weight: 293.409
• UNII: 8646K54I21
• DSSTox Substance ID: DTXSID50873786
• Nikkaji Number: J345.919E
• Wikidata: Q27269700
• Metabolomics Workbench ID: 42514
• ChEMBL ID: CHEMBL3544582
• Mol file: 64520-05-4.mol

Synonyms:10-hydroxyamitriptyline;10-hydroxyamitriptyline, (E)-isomer;10-hydroxyamitriptyline, (Z)-isomer

Chemical Property of (E)-10-Hydroxyamitriptyline

Chemical Property:

• Vapor Pressure: 5.23E-09mmHg at 25°C
• Melting Point: 97-99?°C
• Boiling Point: 453.3°Cat760mmHg
• PKA: 13.89±0.20(Predicted)
• Flash Point: 225.4°C
• Density: 1.151g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: 0.1 M HCl: soluble
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 293.177964357
• Heavy Atom Count: 22
• Complexity: 389

Purity/Quality:

98%,99%, ^*data from raw suppliers

10-Hydroxy(E)-Amitriptyline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Isomeric SMILES: CN(C)CC/C=C/1\C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Uses: (5E)-5-[3-(dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol is a metabolite of amitriptyline (A633350) which is a dibenzocycloheptadiene derivative and an antidepressant (1). Amitriptyline is also a TrkA and TrkB receptor agonist and exhibits neurotrophic and anti-inflammatory activities (2,3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA).

Technology Process of (E)-10-Hydroxyamitriptyline

There total 3 articles about (E)-10-Hydroxyamitriptyline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

amitriptyline hydrochloride (549-18-8,8058-15-9) → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5) + 10-Hydroxynortriptyline (1156-99-6) + (Z)-10-Hydroxyamitriptyline (64520-05-4)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P_450BM3 F₈₇A/H₁₇₁L/Q₃₀₇H/N₃₁₉Y mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt; In ethanol; at 25 ℃; for 2h; pH=8.5; Enzymatic reaction;

DOI:10.1002/chem.201502020

Reference yield:

amitriptyline hydrochloride (549-18-8,8058-15-9) → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5) + (Z)-10-Hydroxyamitriptyline (64520-05-4)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P_450BM3 R₄₇L/Y₅₁F/V₇₈I/A₁₉₁T/N₂₃₉H/I₂₅₉V/A₂₇₆T/A₃₃₀P/L₃₅₃I mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt; In ethanol; at 25 ℃; for 2h; pH=8.5; Enzymatic reaction;

DOI:10.1002/chem.201502020

Reference yield:

amitryptyline (50-48-6) → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5) + (Z)-N,N-dimethyl-3-(10,11-dihydro-10-hydroxy-5H-dibenzocycloheptene)-Δ5,γ-propylamine (1159-82-6) + (-)-(E)-10-Hydroxy-Amitriptylline (64520-05-4,129312-48-7,129312-49-8)

Guidance literature:

With glucose-6-phosphate dehydrogenase; Tris-HCl buffer; α-D-glucose 6-phosphate; liver microsomes of Wistar rats; NADPH; magnesium chloride; In water; at 37 ℃; Rate constant; Product distribution;

DOI:10.1111/j.2042-7158.1996.tb06003.x

upstream raw materials:

amitryptyline

amitriptyline hydrochloride

Downstream raw materials:

(+)-(Z)-10-Hydroxy-Nortriptyline

Refernces

• 1、 Masubuchi, Yasuhiro,Iwasa, Takashi,Fujita, Shoichi,Suzuki, Tokuji,Horie, Toshiharu,Narimatsu, Shizuo. "Regioselectivity and substrate concentration-dependency of involvement of the CYP2D subfamily in oxidative metabolism of amitriptyline and nortriptyline in rat liver microsomes". . p. 925 - 929. Retrieved 2007/10/03.