Amitriptylinoxide

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]

Amitriptylinoxide

Clinical data
Trade names	Amioxid, Ambivalon, Equilibrin
Routes of administration	Oral
ATC code	N06AA25 (WHO)
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
DrugBank	DB13114
ChemSpider	19137 Y
UNII	TYR2U59WMA
KEGG	D07449 Y
ChEBI	CHEBI:135224
ChEMBL	ChEMBL627 Y
CompTox Dashboard (EPA)	DTXSID50195758
ECHA InfoCard	100.119.550
Chemical and physical data
Formula	C20H23NO
Molar mass	293.410 g·mol−1
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
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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

• Imipraminoxide