Opipramol

Opipramol
Clinical data
Trade names	Insidon, Pramolan, others
Other names	G-33040; RP-8307
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06AA05 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	94%
Protein binding	91%
Metabolism	CYP2D6-mediated
Elimination half-life	6–11 hours
Excretion	Urine (70%), feces (10%)
Identifiers
	IUPAC name 4-[3-(5H-dibenz[b,f]azepin- 5-yl)propyl]-1-piperazinethanol;
CAS Number	315-72-0 ; 909-39-7 (dihydrochloride);
PubChem CID	9417;
ChemSpider	9046 ;
UNII	D23ZXO613C;
KEGG	D08297 ;
ChEMBL	ChEMBL370753 ;
CompTox Dashboard (EPA)	DTXSID3023394 ;
ECHA InfoCard	100.005.687
Chemical and physical data
Formula	C23H29N3O
Molar mass	363.505 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OCCN1CCN(CC1)CCCN4c2ccccc2\C=C/c3ccccc34;
	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 ; Key:YNZFUWZUGRBMHL-UHFFFAOYSA-N ;
	(what is this?) (verify)

Opipramol, sold under the brand name Insidon among others, is an anxiolytic and tricyclic antidepressant that is used throughout Europe.^[1]^[4]^[5]^[6]^[7] Despite chemically being a tricyclic dibenzazepine (iminostilbene) derivative similar to imipramine, opipramol is not a monoamine reuptake inhibitor like most other tricyclic antidepressants, and instead, uniquely among antidepressants, acts primarily as a SIGMAR1 agonist.^[7] It was developed by Schindler and Blattner in 1961.^[8]

^ ^a ^b Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e Cite error: The named reference Mohapatra_2013 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ 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. S2CID 27014778.
^ ^a ^b 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–S197. doi:10.1055/s-2004-832677. PMID 15547785. S2CID 260238755.
^ Grosser HH, Ryan E (February 1965). "Drug Treatment of Anxiety: A Controlled Study of Opipramol and Chlordiazepoxide". The British Journal of Psychiatry. 111 (471): 134–141. doi:10.1192/bjp.111.471.134. PMID 14270525. S2CID 40241272.

[Elks2014-1] Cite error: The named reference Elks2014 was invoked but never defined (see the help page).

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Mohapatra_2013-3] Cite error: The named reference Mohapatra_2013 was invoked but never defined (see the help page).

[IndexNominum2000-4] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[Drugs.com-5] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[pmid11199949-6] 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. S2CID 27014778.

[pmid15547785-7] 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–S197. doi:10.1055/s-2004-832677. PMID 15547785. S2CID 260238755.

[pmid14270525-8] Grosser HH, Ryan E (February 1965). "Drug Treatment of Anxiety: A Controlled Study of Opipramol and Chlordiazepoxide". The British Journal of Psychiatry. 111 (471): 134–141. doi:10.1192/bjp.111.471.134. PMID 14270525. S2CID 40241272.

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