10-Hydroxynortriptyline

Base Information

• Chemical Name: 10-Hydroxynortriptyline
• CAS No.: 47132-19-4
• Molecular Formula: C₁₉H₂₁NO
• Molecular Weight: 279.382
• UNII: 7A43OTR1B8,DQQ770F8UO,411I184MG3
• Nikkaji Number: J346.736H
• ChEMBL ID: CHEMBL3638287
• Mol file: 47132-19-4.mol

Synonyms:10-hydroxynortriptyline;10-hydroxynortriptyline hydrochloride;10-hydroxynortriptyline maleate (1:1);10-hydroxynortriptyline, (+-)-isomer;10-hydroxynortriptyline, (E)-isomer;10-hydroxynortriptyline, (Z)-isomer

Chemical Property of 10-Hydroxynortriptyline

Chemical Property:

• Melting Point: 88-93°C
• PSA: 32.26000
• LogP: 3.70820
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 279.162314293
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

97% ^*data from raw suppliers

cis-10-Hydroxy Nortriptyline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC=C1C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Isomeric SMILES: CNCC/C=C\1/C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Uses: A metabolite of Nortriptyline (N837000). A metabolite of Nortriptyline (N837000)

Technology Process of 10-Hydroxynortriptyline

There total 17 articles about 10-Hydroxynortriptyline 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: 89.0%

5-[3-Bromo-prop-(Z)-ylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol (156458-91-2) + methylamine (74-89-5) → (+)-(Z)-10-Hydroxy-Nortriptyline (47132-19-4,115460-05-4,115460-06-5)

Guidance literature:

In acetonitrile; at 60 ℃; for 5h;

DOI:10.1080/00397919408010157

Reference yield:

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5) → Desmethylnortriptyline (4444-42-2) + (+)-(Z)-10-Hydroxy-Nortriptyline (47132-19-4,115460-05-4,115460-06-5) + (E)-10-Hydroxynortriptyline (47132-16-1,112839-35-7,112839-36-8)

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

Reference yield:

10-piperidin-1-yl-dibenzo[a,d]cyclohepten-5-one (37439-92-2) → (+)-(Z)-10-Hydroxy-Nortriptyline (47132-19-4,115460-05-4,115460-06-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h

2: 100 percent / 0.1N HCl / methanol / 6 h

3: 67 percent / CBr₄, PPh₃ / CH₂Cl₂ / 2 h / 0 °C

4: 100 percent / NaBH₄ / methanol / 1 h / Ambient temperature

5: 89 percent / acetonitrile / 5 h / 60 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; triphenylphosphine; In methanol; dichloromethane; acetonitrile;

DOI:10.1080/00397919408010157

upstream raw materials:

(Z)-N-methyl-3-(10,11-dihydro-10-oxo-5H-dibenzocycloheptene)-Δ^5,γ-propylamine

5-[3-Bromo-prop-(Z)-ylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol

methylamine

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

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.
• 2、 Lassen,Perregaard. "Synthesis and NMR studies of Z- and E-isomers of 10-oxo and 10-hydroxy derivatives of amitriptyline and nortriptyline". . p. 335 - 340. Retrieved 2007/10/02.