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O5889

Sigma-Aldrich

Opipramol dihydrochloride

≥98% (HPLC), solid

Synonym(s):

4-[3-(5H-Dibenz[b,f]azepin-5-yl)propyl]-1-piperazineethanol dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H29N3O · 2HCl
CAS Number:
909-39-7
Molecular Weight:
436.42
EC Number:
213-000-2
MDL number:
MFCD00941483
UNSPSC Code:
12352200
PubChem Substance ID:
24724565
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

yellow

solubility

H2O: ~24 mg/mL

SMILES string

Cl[H].Cl[H].OCCN1CCN(CCCN2c3ccccc3C=Cc4ccccc24)CC1

InChI

1S/C23H29N3O.2ClH/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;2*1H

InChI key

DLTOEESOSYKJBK-UHFFFAOYSA-N

General description

Opipramol acts as an antidepressant and is chemically similar to tricyclic antidepressants. It is an atypical anxiolytic and antidepressant drug. Opipramol mainly acts on sigma receptors. It is usually found to be much effective in depressive disorder. It has the ability to prevent histamine, serotonin, dopamine and alpha-1 adrenergic receptors.

Biochem/physiol Actions

σ1/σ2 opioid receptor agonist; an antagonist at D2, 5HT2 and H1 receptors; atypical antidepressant, antipsychotic and anxiolytic

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000268262
0000268261
0000127998
0000227987
0000232286

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H-P Volz et al.
Pharmacopsychiatry, 37 Suppl 3, S214-S220 (2004-11-18)
So far, sigma-ligands have been investigated for several indications in human studies in functional diarrhea as a model of somatoform disorder (igmesine), depression (igmesine, opipramol), anxiety (opipramol and--in animal models--siramisine), schizophrenia (panamasine, SL 82.0715, rimcazole, DuP 734, BMY 14 802)
Opipramol as nighttime medication.
Ulrich Leutgeb
Deutsches Arzteblatt international, 106(18), 321-321 (2009-06-24)
W E Müller et al.
Pharmacopsychiatry, 37 Suppl 3, S189-S197 (2004-11-18)
Although opipramol is structurally related to imipramine, it does not represent a tricyclic antidepressant drug as it does not inhibit the neuronal uptake of norepinephrine and/or serotonin. Unlike imipramine it is a rather potent sigma ligand with modest subclass selectivity
[Opipramol (Insidon) in the treatment of somatoform disorders].
H J Freyberger et al.
Fortschritte der Neurologie-Psychiatrie, 66 Suppl 1, S25-S30 (1999-01-29)
Michael Hueppe et al.
Neuropsychobiology, 64(1), 24-31 (2011-05-18)
Due to its pharmacological properties, opipramol may be useful in the context of evening premedication in anaesthesiology. This trial examines whether quality of sleep the night prior to surgery can be improved by opipramol and whether this effect is dose
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