4317-14-0 Usage
Description
Amitriptyline N-oxide is a metabolite of the tricyclic antidepressant drug amitriptyline, which is formed through the action of certain fungi colonizing cadavers. It is involved in the metabolic process of drugs and has been studied using techniques such as LC-ESI-MS/MS and GC-MS.
Uses
Used in Pharmaceutical Industry:
Amitriptyline N-oxide is used as an intermediate in the development of antidepressant drugs, contributing to the understanding of drug metabolism and the improvement of antidepressant medications.
Used in Forensic Science:
In the field of forensic science, amitriptyline N-oxide is utilized in biological studies to analyze the metabolic processes of drugs by fungi colonizing cadavers. This helps in the identification and understanding of drug interactions and decomposition in post-mortem scenarios.
Originator
Equilibrin,Nattermann,W. Germany,1980
Manufacturing Process
31.3 g (0.1 mol) of 3-(3'-dimethylaminopropylidene)dibenzo[a,d]cyclohepta-
1,4-diene hydrochloride are dissolved in water, and the free base is liberated
by means of a 28% aqueous solution of sodium hydroxide. The free base is
sucked off, washed with water, and dissolved in 100 ml of methanol. To the
solution are added 31 ml of 30% hydrogen peroxide. After 7 days, the
reaction mixture is diluted with 200 ml of water, and the major part of the
methanol is evaporated in vacuum. The precipitated N-oxide crystals are
filtered off, washed with water, and dried, yielding 27 g of the dihydrate of 3-
(3'-dimethylaminopropylidene)dibenzo[a,d]cyclohepta-1,4-diene N-oxide with
melting point of 102° to 103°C. In dehydrated state the melting point is
228°C to 230°C.
By dissolving the N-oxide in acetone, and bubbling dry hydrogen chlorine gas
through the solution until slightly acid reaction, the hydrochloride of the Noxide
is precipitated as a white crystalline substance with melting point of
172°C to 173.6°C.
The starting material can be prepared in known manner from
dibenzo[a,d]cyclohepta-1,4-diene-5-one by a Grignard reaction with 3-
dimethylaminopropyl magnesium chloride, hydrolysis and dehydration of the
resulting carbinol.
Therapeutic Function
Antidepressant
Safety Profile
Poison by ingestion,intraperitoneal, and intravenous routes. An experimentalteratogen. Other experimental reproductive effects. Whenheated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 4317-14-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,1 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4317-14:
(6*4)+(5*3)+(4*1)+(3*7)+(2*1)+(1*4)=70
70 % 10 = 0
So 4317-14-0 is a valid CAS Registry Number.
InChI:InChI=1/C20H23NO/c1-21(2,22)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
4317-14-0Relevant articles and documents
A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water
Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.
supporting information; experimental part, p. 5690 - 5693 (2010/11/05)
A simple and convenient protocol for deoxygenation of aliphatic and aromatic N-oxides to the corresponding amines in good to excellent yield using sodium borohydride-Raney nickel in water is reported. Other functional moieties such as alkenes, halides, ethers, and amides are unaffected under the present reaction condition.
