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Opipramol

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Name

Opipramol

EINECS 206-254-0
CAS No. 315-72-0 Density 1.129 g/cm3
PSA 29.95000 LogP 3.24930
Solubility N/A Melting Point 100-1010C
Formula C23H29 N3 O Boiling Point 555.1 °C at 760 mmHg
Molecular Weight 363.503 Flash Point 290.5 °C
Transport Information N/A Appearance N/A
Safety Poison by intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by ingestion. Many dibenz-azepine compounds have central nervous system effects. When heated to decomposition it emits toxic fumes of NOx. Risk Codes 22-50/53
Molecular Structure Molecular Structure of 315-72-0 (Opipramol) Hazard Symbols Xn,N
Synonyms

5H-Dibenz[b,f]azepine,1-piperazineethanol deriv.;4-[3-(5H-Dibenz[b,f]azepin-5-yl)propyl]-1-piperazineethanol;Endison;G 33040;GR 33040;N-[3-[4-(2-Hydroxyethyl)piperazino]propyl]iminostilbene;NSC 169867;Opipramol G;Opramidol;1-Piperazineethanol,4-[3-(5H-dibenz[b,f]azepin-5-yl)propyl]-;

Article Data 12

Opipramol Specification

1. Introduction of Opipramol
Opipramol is one kind of crystalline solid. The IUPAC Name of this chemical is 2-[4-(3-Benzo[B][1]Benzazepin-11-Ylpropyl)Piperazin-1-Yl]Ethanol. Opipramol belongs to Intermediates & Fine Chemicals; Pharmaceuticals. The Classification Code of Opipramol is Adrenergic Agents is Adrenergic uptake inhibitors; Antidepressive Agents; Antidepressive agents, tricyclic; Central Nervous System Agents; Drug / Therapeutic Agent; Neurotransmitter Agents; Neurotransmitter Uptake; Inhibitors; Psychotropic Drugs. Besides, Opipramol can soluble in chlorform and methanol.

2. Properties of Opipramol
Physical properties about Opipramol are:
(1)Density: 1.129 g/cm3; (2)Melting Point: 100-1010°C; (3)Flash Point: 290.5 °C; (4)Boiling Point: 555.1 °C at 760 mmHg; (5)Vapour Pressure: 3.72E-13 mmHg at 25°C; (6)Enthalpy of Vaporization: 88 kJ/mol; (7)XLogP3-AA: 3.6; (8)H-Bond Donor: 1; (9)H-Bond Acceptor: 4; (10)Rotatable Bond Count: 6; (11)Exact Mass: 363.231063; (12)MonoIsotopic Mass: 363.231063; (13)Topological Polar Surface Area: 30; (14)Heavy Atom Count: 27; (15)Formal Charge: 0; (16)Complexity: 448; (17)Isotope Atom Count: 0; (18)Defined Atom Stereocenter Count: 0; (19)Undefined Atom Stereocenter Count: 0; (20)Defined Bond Stereocenter Count: 0; (21)Undefined Bond Stereocenter Count: 0; (22)Covalently-Bonded Unit Count: 1; (23)Feature 3D Acceptor Count: 1; (24)Feature 3D Donor Count: 1; (25)Feature 3D Cation Count: 3; (26)Feature 3D Ring Count: 4; (27)Effective Rotor Count: 7.4; (28)Conformer Sampling RMSD: 0.8.

3. Structure Descriptors of Opipramol
(1)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
(2)InChIKey: YNZFUWZUGRBMHL-UHFFFAOYSA-N
(3)Canonical SMILES: C1CN(CCN1CCCN2C3=CC=CC=C3C=CC4=CC=CC=C42)CCO
(4)Smiles: N1(c2c(C=Cc3c1cccc3)cccc2)CCCN1CCN(CC1)CCO

4. Toxicity of Opipramol

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
mouse LD50 intravenous 45mg/kg (45mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
mouse LD50 oral 400mg/kg (400mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 181, Pg. 68, 1969.
mouse LD50 subcutaneous 315mg/kg (315mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rabbit LD50 intravenous 11mg/kg (11mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rat LD50 intraperitoneal 95mg/kg (95mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rat LD50 intravenous 32mg/kg (32mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rat LD50 oral 1110mg/kg (1110mg/kg)   Farmaco, Edizione Pratica. Vol. 25, Pg. 519, 1970.
rat LD50 subcutaneous 497mg/kg (497mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.

5. Safety information of Opipramol
Poison by intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by ingestion. Many dibenz-azepine compounds have central nervous system effects. When heated to decomposition it emits toxic fumes of NOx.

6. Uses of Opipramol
Opipramol (CAS NO.315-72-0) is a psychoactive drug widely used as an anxiolytic in Germany. Although it is a member of the tricyclic antidepressants (TCAs), 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 other properties. Also it was used as Antidepressant and Antipsychotic.It 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. 

It 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.

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