MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 414401 | Name: Opipramol Free Base
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Opipramol Free Base is a tricyclic antidepressant with actions similar to amitriptyline. As of 2024, Opipramol is not approved for marketing in the United States, but is available overseas. At 100 muM, opipramol inhibits glucose incorporation into lipids without limiting the glucose transport in mouse adipocytes.

Chemical Structure

Opipramol Free Base
Opipramol Free Base
CAS#315-72-0 (free base)

Theoretical Analysis

MedKoo Cat#: 414401

Name: Opipramol Free Base

CAS#: 315-72-0 (free base)

Chemical Formula: C23H29N3O

Exact Mass: 363.2311

Molecular Weight: 363.51

Elemental Analysis: C, 76.00; H, 8.04; N, 11.56; O, 4.40

Price and Availability

Size Price Availability Quantity
5mg USD 415.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 775.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
315-72-0 (free base) 909-39-7 (HCl)
Synonym
Opipramol Free Base; BRN0627076; BRN-0627076; BRN 0627076
IUPAC/Chemical Name
1-Piperazineethanol, 4-(3-(5H-dibenz(b,f)azepin-5-yl)propyl)-
InChi Key
YNZFUWZUGRBMHL-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OCCN1CCN(CCCN2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Opipramol (Ensidon) is an atypical tricyclic antidepressant (TCA). Opipramol acts primarily as a sigma (σ) receptor agonist.
In vitro activity:
To examine whether opipramol reproduces or impairs other actions of insulin, its direct effects on glucose transport, lipogenesis and lipolysis were investigated in adipocytes while its influence on insulin secretion was studied in pancreatic islets. At 100 μM, opipramol also inhibited the glucose incorporation into lipids without limiting the glucose transport in mouse adipocytes. In pancreatic islets, opipramol acutely impaired the stimulation of insulin secretion by various activators (high glucose, high potassium, forskolin...). Reference: J Physiol Biochem. 2023 Feb 23. https://pubmed.ncbi.nlm.nih.gov/36821072/
In vivo activity:
Opipramol potently increased the metabolism of dopamine in the striatum, olfactory tubercle and pyriform cortex of the rat and increased the release of dopamine from the striatum of the mouse, as measured by increases in the levels of 3-methoxytyramine in vivo. Opipramol increased plasma prolactin in the rat, only at a dose as large as 50 mg/kg dose. Irreversible inactivation of dopamine receptors by EEDQ (N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline) did not affect the opipramol-induced increases in levels of dihydroxyphenylacetic acid (DOPAC) in the striatum of the rat, indicating a predominant role of activation of sigma receptors in the dopaminergic effects of opipramol. However, pretreatment with the putative sigma ligand, rimcazole, markedly potentiated the ability of opipramol to increase the metabolism of release of DA in the striatum of the mouse in vivo. Reference: Neuropharmacology. 1990 Dec;29(12):1191-7. https://pubmed.ncbi.nlm.nih.gov/1963476/

Preparing Stock Solutions

The following data is based on the product molecular weight 363.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Iglesias-Osma MC, García-Barrado MJ, Hernandez-Gonzalez D, Perrier K, Viana P, Carpéné C. The anxiolytic drug opipramol inhibits insulin-induced lipogenesis in fat cells and insulin secretion in pancreatic islets. J Physiol Biochem. 2023 Feb 23. doi: 10.1007/s13105-023-00950-8. Epub ahead of print. PMID: 36821072. 2. Carpéné C, Les F, Mercader J, Gomez-Zorita S, Grolleau JL, Boulet N, Fontaine J, Iglesias-Osma MC, Garcia-Barrado MJ. Opipramol Inhibits Lipolysis in Human Adipocytes without Altering Glucose Uptake and Differently from Antipsychotic and Antidepressant Drugs with Adverse Effects on Body Weight Control. Pharmaceuticals (Basel). 2020 Mar 5;13(3):41. doi: 10.3390/ph13030041. PMID: 32151075; PMCID: PMC7151722. 3. Bareli T, Ahdoot HL, Ben-Moshe H, Barnea R, Warhaftig G, Maayan R, Roska P, Weizman A, Yadid G. Chronic opipramol treatment extinguishes cocaine craving through Rac1 in responders: A rat model study. Addict Biol. 2021 Sep;26(5):e13014. doi: 10.1111/adb.13014. Epub 2021 Jan 28. PMID: 33508873. 4. Rao TS, Cler JA, Mick SJ, Dilworth VM, Contreras PC, Iyengar S, Wood PL. Neurochemical characterization of dopaminergic effects of opipramol, a potent sigma receptor ligand, in vivo. Neuropharmacology. 1990 Dec;29(12):1191-7. doi: 10.1016/0028-3908(90)90044-r. PMID: 1963476.
In vitro protocol:
1. Iglesias-Osma MC, García-Barrado MJ, Hernandez-Gonzalez D, Perrier K, Viana P, Carpéné C. The anxiolytic drug opipramol inhibits insulin-induced lipogenesis in fat cells and insulin secretion in pancreatic islets. J Physiol Biochem. 2023 Feb 23. doi: 10.1007/s13105-023-00950-8. Epub ahead of print. PMID: 36821072. 2. Carpéné C, Les F, Mercader J, Gomez-Zorita S, Grolleau JL, Boulet N, Fontaine J, Iglesias-Osma MC, Garcia-Barrado MJ. Opipramol Inhibits Lipolysis in Human Adipocytes without Altering Glucose Uptake and Differently from Antipsychotic and Antidepressant Drugs with Adverse Effects on Body Weight Control. Pharmaceuticals (Basel). 2020 Mar 5;13(3):41. doi: 10.3390/ph13030041. PMID: 32151075; PMCID: PMC7151722.
In vivo protocol:
1. Bareli T, Ahdoot HL, Ben-Moshe H, Barnea R, Warhaftig G, Maayan R, Roska P, Weizman A, Yadid G. Chronic opipramol treatment extinguishes cocaine craving through Rac1 in responders: A rat model study. Addict Biol. 2021 Sep;26(5):e13014. doi: 10.1111/adb.13014. Epub 2021 Jan 28. PMID: 33508873. 2. Rao TS, Cler JA, Mick SJ, Dilworth VM, Contreras PC, Iyengar S, Wood PL. Neurochemical characterization of dopaminergic effects of opipramol, a potent sigma receptor ligand, in vivo. Neuropharmacology. 1990 Dec;29(12):1191-7. doi: 10.1016/0028-3908(90)90044-r. PMID: 1963476.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Opipramol. 2024 Jun 15. PMID: 38913819. 2: Bailly C, Degand C, Laine W, Sauzeau V, Kluza J. Implication of Rac1 GTPase in molecular and cellular mitochondrial functions. Life Sci. 2024 Apr 1;342:122510. doi: 10.1016/j.lfs.2024.122510. Epub 2024 Feb 20. PMID: 38387701. 3: Iglesias-Osma MC, García-Barrado MJ, Hernandez-Gonzalez D, Perrier K, Viana P, Carpéné C. The anxiolytic drug opipramol inhibits insulin-induced lipogenesis in fat cells and insulin secretion in pancreatic islets. J Physiol Biochem. 2023 May;79(2):415-425. doi: 10.1007/s13105-023-00950-8. Epub 2023 Feb 23. PMID: 36821072. 4: Frontiers Production Office. Erratum: Novel Opipramol-Baclofen Combination Alleviates Depression and Craving and Facilitates Recovery From Substance Use Disorder-An Animal Model and a Human Study. Front Behav Neurosci. 2022 Jun 10;16:952004. doi: 10.3389/fnbeh.2022.952004. Erratum for: Front Behav Neurosci. 2021 Dec 23;15:788708. doi: 10.3389/fnbeh.2021.788708. PMID: 35755408; PMCID: PMC9231432. 5: Bareli T, Ahdoot HL, Ben Moshe H, Barnea R, Warhaftig G, Gispan I, Maayan R, Rosca P, Weizman A, Yadid G. Novel Opipramol-Baclofen Combination Alleviates Depression and Craving and Facilitates Recovery From Substance Use Disorder-An Animal Model and a Human Study. Front Behav Neurosci. 2021 Dec 23;15:788708. doi: 10.3389/fnbeh.2021.788708. Erratum in: Front Behav Neurosci. 2022 Jun 10;16:952004. doi: 10.3389/fnbeh.2022.952004. PMID: 35002647; PMCID: PMC8733380. 6: Jørgensen CK, Juul S, Siddiqui F, Barbateskovic M, Munkholm K, Hengartner MP, Kirsch I, Gluud C, Jakobsen JC. Tricyclic antidepressants versus 'active placebo', placebo or no intervention for adults with major depressive disorder: a protocol for a systematic review with meta-analysis and Trial Sequential Analysis. Syst Rev. 2021 Aug 13;10(1):227. doi: 10.1186/s13643-021-01789-0. PMID: 34389045; PMCID: PMC8361619. 7: Müller E, Hillemacher T, Müller CP. Kratom use for depression/anxiety self- management: challenges during the COVID-19 pandemic - A case report. Heliyon. 2021 May 10;7(5):e07039. doi: 10.1016/j.heliyon.2021.e07039. PMID: 34136676; PMCID: PMC8180622. 8: Juul S, Siddiqui F, Barbateskovic M, Jørgensen CK, Hengartner MP, Kirsch I, Gluud C, Jakobsen JC. Beneficial and harmful effects of antidepressants versus placebo, 'active placebo', or no intervention for adults with major depressive disorder: a protocol for a systematic review of published and unpublished data with meta-analyses and trial sequential analyses. Syst Rev. 2021 May 25;10(1):154. doi: 10.1186/s13643-021-01705-6. PMID: 34034811; PMCID: PMC8152051. 9: Bareli T, Ahdoot HL, Ben-Moshe H, Barnea R, Warhaftig G, Maayan R, Roska P, Weizman A, Yadid G. Chronic opipramol treatment extinguishes cocaine craving through Rac1 in responders: A rat model study. Addict Biol. 2021 Sep;26(5):e13014. doi: 10.1111/adb.13014. Epub 2021 Jan 28. PMID: 33508873. 10: Wieckiewicz M, Martynowicz H, Wieczorek T, Wojakowska A, Sluzalec- Wieckiewicz K, Gac P, Poreba R, Mazur G, Winocur E, Smardz J. Consecutive Controlled Case Series on Effectiveness of Opipramol in Severe Sleep Bruxism Management-Preliminary Study on New Therapeutic Path. Brain Sci. 2021 Jan 22;11(2):146. doi: 10.3390/brainsci11020146. PMID: 33499332; PMCID: PMC7911172. 11: Carpéné C, Les F, Mercader J, Gomez-Zorita S, Grolleau JL, Boulet N, Fontaine J, Iglesias-Osma MC, Garcia-Barrado MJ. Opipramol Inhibits Lipolysis in Human Adipocytes without Altering Glucose Uptake and Differently from Antipsychotic and Antidepressant Drugs with Adverse Effects on Body Weight Control. Pharmaceuticals (Basel). 2020 Mar 5;13(3):41. doi: 10.3390/ph13030041. PMID: 32151075; PMCID: PMC7151722. 12: Emamghoreishi M, Shahpari M, Keshavarz M. Interaction of sigma-1 receptor modulators with seizure development in pentylenetetrazole-induced kindled mice. Epilepsy Res. 2019 Aug;154:74-76. doi: 10.1016/j.eplepsyres.2019.05.001. Epub 2019 May 2. PMID: 31078073. 13: Kollhorst B, Jobski K, Krappweis J, Schink T, Garbe E, Schmedt N. Antidepressants and the risk of death in older patients with depression: A population-based cohort study. PLoS One. 2019 Apr 15;14(4):e0215289. doi: 10.1371/journal.pone.0215289. PMID: 30986235; PMCID: PMC6464187. 14: Pisa FE, Reinold J, Kollhorst B, Haug U, Schink T. Antidepressants and the risk of traumatic brain injury in the elderly: differences between individual agents. Clin Epidemiol. 2019 Feb 15;11:185-196. doi: 10.2147/CLEP.S173667. PMID: 30858730; PMCID: PMC6386209. 15: Rozanski V, Laux G, Schwarz J. The Dopamine Receptor Antagonism of Opipramol: Relevance to Parkinsonism? Clin Neuropharmacol. 2019 May/Jun;42(3):77-79. doi: 10.1097/WNF.0000000000000332. PMID: 30829882. 16: Pochernikov DG, Strelnikov AI, Bazunov DS, Efimychev KA, Serdyutskaya US. [The incidence and antibiotic resistance of common nosocomial uropathogens in the urine of urological patients in the Ivanovo region]. Urologiia. 2018 Jul;(3):49-53. Russian. PMID: 30035418. 17: Keshavarz M, Yekzaman B. Amelioration of Pentylenetetrazole-Induced Seizures by Modulators of Sigma, N-Methyl-D-Aspartate, and Ryanodine Receptors in Mice. Iran J Med Sci. 2018 Mar;43(2):195-201. PMID: 29749988; PMCID: PMC5936851. 18: Ebhuoma O, Gebreslasie M, Magubane L. Modeling malaria control intervention effect in KwaZulu-Natal, South Africa using intervention time series analysis. J Infect Public Health. 2017 May-Jun;10(3):334-338. doi: 10.1016/j.jiph.2017.02.011. Epub 2017 Mar 18. PMID: 28330701. 19: Gahr M, Hiemke C, Connemann BJ. Update Opipramol [Update Opipramol]. Fortschr Neurol Psychiatr. 2017 Mar;85(3):139-145. German. doi: 10.1055/s-0043-100762. Epub 2017 Mar 20. PMID: 28320023. 20: Krysta K, Murawiec S, Warchala A, Zawada K, Cubała WJ, Wiglusz MS, Jakuszkowiak-Wojten K, Krzystanek M, Krupka-Matuszczyk I. Modern indications for the use of opipramol. Psychiatr Danub. 2015 Sep;27 Suppl 1:S435-7. PMID: 26417811.