Amitriptylinoxide

Amitriptylinoxide

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 3-(10,11-dihydro- 5H-dibenzo[a,d]cycloheptene- 5-ylidene)- N,N-dimethyl- 1-propanamine N-oxide
CAS Number	4317-14-0 Y
PubChem CID	20313
ChemSpider	19137 Y
UNII	TYR2U59WMA
KEGG	D07449 Y
ChEMBL	CHEMBL627 Y
ECHA InfoCard	100.119.550
Chemical and physical data
Formula	C20H23NO
Molar mass	293.40 g/mol
3D model (JSmol)	Interactive image
SMILES [O-][N+](C)(C)CC/C=C2/c1c(cccc1)CCc3c2cccc3
InChI 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 Y Key:ZPMKQFOGINQDAM-UHFFFAOYSA-N Y

Amitriptylinoxide (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.

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant. 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.

In receptor binding assays, amitripylinoxide 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.