Opipramol

Opipramol

Systematic (IUPAC) name
4-[3-(5H-dibenz[b,f]azepin- 5-yl)propyl]-1-piperazinethanol
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral
Identifiers
CAS number	315-72-0 N
ATC code	N06AA05
PubChem	CID 9417
ChemSpider	9046 Y
UNII	D23ZXO613C Y
KEGG	D08297 Y
ChEMBL	CHEMBL370753 Y
Chemical data
Formula	C23H29N3O
Mol. mass	363.496 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C23H29N3O/c27-19-18-25-16-14-24(15-17-25)12-5-13-26-22-8-3-1-6-20(22)10-11-21-7-2-4-9-23(21)26/h1-4,6-11,27H,5,12-19H2 Y Key:YNZFUWZUGRBMHL-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Opipramol (Insidon, Pramolan, Ensidon, Oprimol) is an antidepressant and anxiolytic used in Germany and other European countries. Although it is a member of the tricyclic antidepressants, opipramol's primary mechanism of action is much different in comparison. Most TCAs act as reuptake inhibitors, but opipramol does not, and instead acts as a sigma receptor agonist, among having other properties.

Indications

Opipramol is typically used in the treatment of generalized anxiety disorder (GAD). Its anxiolysis becomes prominent after only 1-2 weeks of chronic administration. Upon first commencing treatment, opipramol is rather sedating in nature due to its antihistamine properties, but this effect becomes less prominent with time.

Pharmacology

Opipramol acts as a high affinity sigma receptor agonist, primarily at the σ₁ subtype, but also at the σ₂ subtype with somewhat lower affinity. It is this property which is responsible for its therapeutic benefits against anxiety and depression. Opipramol also acts as a low to moderate affinity antagonist for the D₂, 5-HT₂, H₁, H₂, and muscarinic acetylcholine receptors. H₁ and H₂ receptor antagonism account for its antihistamine effects, and muscarinic acetylcholine receptor antagonism is responsible for its anticholinergic properties.

Contraindications

Opipramol should not be taken with alcohol, or in patients with benign prostatic hyperplasia (BPH) or glaucoma.

See also

• Tricyclic antidepressant