Amitriptylinoxide

Chemical compound From Wikipedia, the free encyclopedia

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin), or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.[1]

Trade namesAmioxid, Ambivalon, Equilibrin
Routes of
administrationOral
ATC code
Legal status
  • In general: ℞ (Prescription only)
Quick facts Clinical data, Trade names ...
Amitriptylinoxide
Skeletal formula of amitriptylinoxide
Ball-and-stick model of the amitriptylinoxide molecule
Clinical data
Trade namesAmioxid, Ambivalon, Equilibrin
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 3-(10,11-dihydro- 5H-dibenzo[a,d]cycloheptene- 5-ylidene)- N,N-dimethyl- 1-propanamine N-oxide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.550 Edit this at Wikidata
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 g·mol−1
3D model (JSmol)
  • [O-][N+](C)(C)CC/C=C2/c1c(cccc1)CCc3c2cccc3
  • InChI=1S/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 checkY
  • Key:ZPMKQFOGINQDAM-UHFFFAOYSA-N checkY
  (verify)
Close

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant.[2][3][4][5] However, it has a faster onset of action and fewer adverse effects, including reduced drowsiness, sedation, anticholinergic symptoms like dry mouth, sweating, and dizziness, orthostatic hypotension, and cardiotoxicity.[2][3][4][5][6][7]

In receptor binding assays, amitriptylinoxide was found to have generally equivalent pharmacology to amitriptyline, acting as a serotonin and norepinephrine reuptake inhibitor, serotonin receptor antagonist, and H1 receptor antagonist, among other properties, but with approximately 60-fold lower affinity for the α1-adrenergic receptor, and the weakest affinity of any of the TCAs analyzed for the muscarinic acetylcholine receptors.[8][9][10]

Amitriptylinoxide has been said to be a prodrug of amitriptyline.[11]

See also

References

Related Articles

Wikiwand AI