U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H23NO.ClH
Molecular Weight 329.864
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMITRIPTYLINOXIDE HYDROCHLORIDE

SMILES

Cl.C[N+](C)([O-])CCC=C1C2=C(CCC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=ZELYQHCTXSGSGS-UHFFFAOYSA-N
InChI=1S/C20H23NO.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H23NO
Molecular Weight 293.4027
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Amitriptylinoxide (amitriptyline N-oxide, Amioxid, Ambivalon) is a tricyclic antidepressant, which was introduced in Europe in the 1970s for the treatment of depression. Amitriptylinoxide (AMINO) produces similar effects to the drug Amitriptyline (AMI), which makes sense because it is a metabolite of Amitriptyline. AMINO and AMI potentiate the depletion of 5-hydroxytryptamine (5-HT) induced by p-chloroamphetamine in the rat brain and it may be considered as evidence that both drugs do not inhibit 5-HT uptake in vivo. Neither AMINO nor AMI affects the rat brain level of 5-HT but at higher doses they elevate the 5-hydroxy-indoleacetic acid concentrations. AMINO antagonizes the head twitch reaction induced by 5-hydroxytryptophan in mice and tryptamine convulsions in rats. The hyperthermia induced by fenfluramine (in rats at a high ambient temperature) as well as the stimulation of the hind limb flexor reflex in spinal rats, induced by fenfluramine or LSD, are also inhibited. AMINO antagonizes the 5-HT-induced increase in blood pressure in pithed rats. All the above effects are similar to those induced by AMI, only the active doses of AMINO are higher. The results presented indicate that AMINO, like AMI, inhibits NA uptake and is a 5-HT antagonist. Amitriptylinoxide is considered to work more quickly with fewer side effects than Amitriptyline and is regarded as being equal in terms of efficacy. The way the drug works is nearly identical to Amitriptyline, except it affects the Alpha-1 receptors to a significantly lesser extent (60x less) and has among the weakest effects on acetylcholine receptors. Half maximal inhibition of acetylcholine receptor binding occurred for amitriptylinoxide at 18 mumol/l (amitriptyline: 0.32 mumol/l). Comparing all studied antidepressants for muscarinic acetylcholine receptor binding, amitriptylinoxide had the weakest affinity of all tested tricyclic compounds. Also the affinity of amitriptylinoxide for alpha-receptor binding was about 60 fold less than that of amitriptyline. For all antidepressants investigated, the lowest affinities were found for benzodiazepine, opiate and beta-receptor binding. The weak affinities of amitriptylinoxide for various receptors may be responsible for its reduced side-effects, while it still retains potent antidepressant properties by stabilising the amitriptyline-level in the brain.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Polygraphic sleep recordings in patients with endogenous depression before and after treatment with amitriptyline-N-oxide (author's transl)].
1976
The metabolic fate of amitriptyline, nortriptyline and amitriptylinoxide in man.
2004 Oct
Tricyclic antidepressants and headaches: systematic review and meta-analysis.
2010 Oct 20

Sample Use Guides

Eleven healthy volunteers were examined in a pharmacokinetic study. After oral administration of 50 mg amitriptylinoxide or 50 mg amitriptyline the plasma levels of amitriptylinoxide and its main metabolites amitriptyline and nortriptyline were investigated over 24 hours.
Route of Administration: Oral
Amitriptyline, doxepine and clozapine inhibited the release of [3H]-ACh in rat caudatoputamen in a concentration dependent manner. The effects were significant at concentrations of 10 umol/l. Also amitriptylinoxide showed a concentration dependent inhibition, but significance was obtained only at a concentration of 100 umol/l.
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:47:07 GMT 2023
Edited
by admin
on Sat Dec 16 12:47:07 GMT 2023
Record UNII
3UBD0MM0IB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMITRIPTYLINOXIDE HYDROCHLORIDE
Common Name English
1-PROPANAMINE, 3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-, N-OXIDE, HYDROCHLORIDE (1:1)
Systematic Name English
NSC-176555
Code English
AMITRIPTYLINE, N-OXIDE, HYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
6450840
Created by admin on Sat Dec 16 12:47:07 GMT 2023 , Edited by admin on Sat Dec 16 12:47:07 GMT 2023
PRIMARY
FDA UNII
3UBD0MM0IB
Created by admin on Sat Dec 16 12:47:07 GMT 2023 , Edited by admin on Sat Dec 16 12:47:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID00962775
Created by admin on Sat Dec 16 12:47:07 GMT 2023 , Edited by admin on Sat Dec 16 12:47:07 GMT 2023
PRIMARY
NSC
176555
Created by admin on Sat Dec 16 12:47:07 GMT 2023 , Edited by admin on Sat Dec 16 12:47:07 GMT 2023
PRIMARY
CAS
4290-60-2
Created by admin on Sat Dec 16 12:47:07 GMT 2023 , Edited by admin on Sat Dec 16 12:47:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY