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
CAS number 315-72-0 YesY
ATC code N06AA05
PubChem CID 9417
ChemSpider 9046 YesY
KEGG D08297 YesY
Chemical data
Formula C23H29N3O 
Mol. mass 363.496 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Opipramol (Insidon, Pramolan, Ensidon, Oprimol) is an antidepressant and anxiolytic used in Germany and other European countries.[1][2] Although it is a member of the tricyclic antidepressants, opipramol's primary mechanism of action is much different in comparison.[2] Most TCAs act as reuptake inhibitors, but opipramol does not, and instead acts as a sigma receptor agonist, among having other properties.[2]



Opipramol is typically used in the treatment of generalized anxiety disorder (GAD).[1] 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.


Opipramol acts as a high affinity sigma receptor agonist, primarily at the σ1 subtype, but also at the σ2 subtype with somewhat lower affinity.[1] It is this property which is responsible for its therapeutic benefits against anxiety and depression.[2] 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.[1]


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

See also


  1. ^ a b c d Möller HJ, Volz HP, Reimann IW, Stoll KD (February 2001). "Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group". Journal of Clinical Psychopharmacology 21 (1): 59–65. doi:10.1097/00004714-200102000-00011. PMID 11199949. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0271-0749&volume=21&issue=1&spage=59. 
  2. ^ a b c d Müller WE, Siebert B, Holoubek G, Gentsch C (November 2004). "Neuropharmacology of the anxiolytic drug opipramol, a sigma site ligand". Pharmacopsychiatry 37 Suppl 3: S189–97. doi:10.1055/s-2004-832677. PMID 15547785.