Imipramine HCl
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MedKoo CAT#: 318056

CAS#: 113-52-0 (HCl)

Description: Imipramine, sold as Tofranil and also known as melipramine, is a tricyclic antidepressant (TCA) of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination).


Chemical Structure

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Imipramine HCl
CAS# 113-52-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 318056
Name: Imipramine HCl
CAS#: 113-52-0 (HCl)
Chemical Formula: C19H25ClN2
Exact Mass: 0.00
Molecular Weight: 316.873
Elemental Analysis: C, 72.02; H, 7.95; Cl, 11.19; N, 8.84

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
5g USD 550 2 Weeks
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Related CAS #: 113-52-0 (HCl)   50-49-7 (free base),  

Synonym: Imipramine HCl; Imipramine hydrochloride, G 22355, Tofranil, Melipramine, Janimine

IUPAC/Chemical Name: 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride

InChi Key: XZZXIYZZBJDEEP-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H

SMILES Code: CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31

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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:
Biological target: Imipramine hydrochloride is an orally active tertiary amine tricyclic antidepressant. Imipramine hydrochloride is a Fascin1 inhibitor with antitumor activities. Imipramine also inhibits serotonin transporter with an IC50 value of 32 nM. Imipramine hydrochloride stimulates U-87MG glioma cells autophagy and induces HL-60 cell apoptosis. Imipramine hydrochloride shows neuroprotective and immunomodulatory effects.
In vitro activity: To confirm these results in a more physiologically relevant model, this study tested the effect of imipramine treatment in 4T1 isograft model, which closely mimics the aggressive human TNBCs. After 4T1 isograft tumors reached 100 mm3, BALB/c mice were treated with vehicle or 32 mg/kg imipramine for three weeks. Imipramine-treated mice had significantly reduced tumor volumes compared to vehicle-treated 4T1-derived tumors (Supplementary Fig. 1e). Reference: Cancer Lett. 2022 Aug 1;540:215717. https://pubmed.ncbi.nlm.nih.gov/35568265/
In vivo activity: Results show that the gene expression of COX-2, iNOS, and NF-κB was higher in imipramine-treated mice compared with controls (1.5, 1.8, and 1.2 times higher, respectively; Figure 9b,c, respectively). By contrast, the gene expression of IκBα in imipramine-treated mice was 18% lower than that in controls (Figure 9d). These results indicate that imipramine increased the risk of DR (diabetic retinopathy) by elevating inflammation and glucose uptake. Reference: Vet Sci. 2021 Sep 9;8(9):189. https://pubmed.ncbi.nlm.nih.gov/34564583/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 78.90
DMSO 62.7 197.77
Ethanol 44.0 138.86
PBS (pH 7.2) 0.5 1.58
Water 62.8 198.03

Preparing Stock Solutions

The following data is based on the product molecular weight 316.87 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. Timilsina S, Rajamanickam S, Rao A, Subbarayalu P, Nirzhor S, Abdelfattah N, Viswanadhapalli S, Chen Y, Jatoi I, Brenner A, Rao MK, Vadlamudi R, Kaklamani V. The antidepressant imipramine inhibits breast cancer growth by targeting estrogen receptor signaling and DNA repair events. Cancer Lett. 2022 Aug 1;540:215717. doi: 10.1016/j.canlet.2022.215717. Epub 2022 May 12. PMID: 35568265. 2. Wang Y, Wang X, Wang X, Wu D, Qi J, Zhang Y, Wang K, Zhou D, Meng QM, Nie E, Wang Q, Yu RT, Zhou XP. Imipramine impedes glioma progression by inhibiting YAP as a Hippo pathway independent manner and synergizes with temozolomide. J Cell Mol Med. 2021 Oct;25(19):9350-9363. doi: 10.1111/jcmm.16874. Epub 2021 Sep 1. PMID: 34469035; PMCID: PMC8500960. 3. Yueh PF, Lee YH, Chiang IT, Chen WT, Lan KL, Chen CH, Hsu FT. Suppression of EGFR/PKC-δ/NF-κB Signaling Associated With Imipramine-Inhibited Progression of Non-Small Cell Lung Cancer. Front Oncol. 2021 Oct 26;11:735183. doi: 10.3389/fonc.2021.735183. PMID: 34765548; PMCID: PMC8576332. 4. Chang GR, Hou PH, Wang CM, Lin JW, Lin WL, Lin TC, Liao HJ, Chan CH, Wang YC. Imipramine Accelerates Nonalcoholic Fatty Liver Disease, Renal Impairment, Diabetic Retinopathy, Insulin Resistance, and Urinary Chromium Loss in Obese Mice. Vet Sci. 2021 Sep 9;8(9):189. doi: 10.3390/vetsci8090189. PMID: 34564583; PMCID: PMC8473438.
In vitro protocol: 1. Timilsina S, Rajamanickam S, Rao A, Subbarayalu P, Nirzhor S, Abdelfattah N, Viswanadhapalli S, Chen Y, Jatoi I, Brenner A, Rao MK, Vadlamudi R, Kaklamani V. The antidepressant imipramine inhibits breast cancer growth by targeting estrogen receptor signaling and DNA repair events. Cancer Lett. 2022 Aug 1;540:215717. doi: 10.1016/j.canlet.2022.215717. Epub 2022 May 12. PMID: 35568265. 2. Wang Y, Wang X, Wang X, Wu D, Qi J, Zhang Y, Wang K, Zhou D, Meng QM, Nie E, Wang Q, Yu RT, Zhou XP. Imipramine impedes glioma progression by inhibiting YAP as a Hippo pathway independent manner and synergizes with temozolomide. J Cell Mol Med. 2021 Oct;25(19):9350-9363. doi: 10.1111/jcmm.16874. Epub 2021 Sep 1. PMID: 34469035; PMCID: PMC8500960.
In vivo protocol: 1. Yueh PF, Lee YH, Chiang IT, Chen WT, Lan KL, Chen CH, Hsu FT. Suppression of EGFR/PKC-δ/NF-κB Signaling Associated With Imipramine-Inhibited Progression of Non-Small Cell Lung Cancer. Front Oncol. 2021 Oct 26;11:735183. doi: 10.3389/fonc.2021.735183. PMID: 34765548; PMCID: PMC8576332. 2. Chang GR, Hou PH, Wang CM, Lin JW, Lin WL, Lin TC, Liao HJ, Chan CH, Wang YC. Imipramine Accelerates Nonalcoholic Fatty Liver Disease, Renal Impairment, Diabetic Retinopathy, Insulin Resistance, and Urinary Chromium Loss in Obese Mice. Vet Sci. 2021 Sep 9;8(9):189. doi: 10.3390/vetsci8090189. PMID: 34564583; PMCID: PMC8473438.

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1: Hearn L, Derry S, Phillips T, Moore RA, Wiffen PJ. Imipramine for neuropathic pain in adults. Cochrane Database Syst Rev. 2014 May 19;5:CD010769. doi: 10.1002/14651858.CD010769.pub2. Review. PubMed PMID: 24838845.

2: D'Agostino ML, Risser J, Robinson-Bostom L. Imipramine-induced hyperpigmentation: a case report and review of the literature. J Cutan Pathol. 2009 Jul;36(7):799-803. doi: 10.1111/j.1600-0560.2008.01121.x. Review. PubMed PMID: 19519613.

3: Dean CE, Grund FM. Imipramine-associated hyperpigmentation. Ann Pharmacother. 2003 Jun;37(6):825-8. Review. PubMed PMID: 12773071.

4: Hunsballe JM, Djurhuus JC. Clinical options for imipramine in the management of urinary incontinence. Urol Res. 2001 Apr;29(2):118-25. Review. PubMed PMID: 11396729.

5: Barros HM, Ferigolo M. Ethopharmacology of imipramine in the forced-swimming test: gender differences. Neurosci Biobehav Rev. 1998;23(2):279-86. Review. PubMed PMID: 9884121.

6: Yasuda K. [Tricyclic antidepressants (imipramine, desipramine, amitriptyline, nortriptyline)]. Nihon Rinsho. 1995 Feb;53 Su Pt 1:934-7. Review. Japanese. PubMed PMID: 8753592.

7: Ferguson KL. Imipramine-provoked paradoxical pheochromocytoma crisis: a case of cardiogenic shock. Am J Emerg Med. 1994 Mar;12(2):190-2. Review. PubMed PMID: 8161395.

8: Parsons B, Quitkin FM, McGrath PJ, Stewart JW, Tricamo E, Ocepek-Welikson K, Harrison W, Rabkin JG, Wager SG, Nunes E. Phenelzine, imipramine, and placebo in borderline patients meeting criteria for atypical depression. Psychopharmacol Bull. 1989;25(4):524-34. Review. PubMed PMID: 2698483.

9: Mavissakalian M. Differential effects of imipramine and behavior therapy on panic disorder with agoraphobia. Psychopharmacol Bull. 1989;25(1):27-9. Review. PubMed PMID: 2672069.

10: Hrdina PD. Imipramine binding sites in brain and platelets: role in affective disorders. Int J Clin Pharmacol Res. 1989;9(2):119-22. Review. PubMed PMID: 2541089.

11: Plenge P, Mellerup ET, Gjerris A. Imipramine binding in depressive patients diagnosed according to different criteria. Acta Psychiatr Scand. 1988 Aug;78(2):156-61. Review. PubMed PMID: 2851919.

12: Bech P, Eplov L, Gastpar M, Gentsch C, Mendlewicz J, Plenge P, Rielaert C, Mellerup ET. WHO pilot study on the validity of imipramine platelet receptor binding sites as a biological marker of endogenous depression. A preliminary report on the initial evaluation phase of a World Health Organization Collaborative Study. Pharmacopsychiatry. 1988 May;21(3):147-50. Review. PubMed PMID: 2841696.

13: Gram LF. Imipramine: a model substance in pharmacokinetic research. Acta Psychiatr Scand Suppl. 1988;345:81-4. Review. PubMed PMID: 3067542.

14: Mellerup ET, Plenge P. Imipramine binding in depression and other psychiatric conditions. Acta Psychiatr Scand Suppl. 1988;345:61-8. Review. PubMed PMID: 2852451.

15: Boschmans SA, Perkin MF, Terblanche SE. Antidepressant drugs: imipramine, mianserin and trazodone. Comp Biochem Physiol C. 1987;86(2):225-32. Review. PubMed PMID: 2882911.

16: Asberg M, Wägner A. Biochemical effects of antidepressant treatment--studies of monoamine metabolites in cerebrospinal fluid and platelet [3H]imipramine binding. Ciba Found Symp. 1986;123:57-83. Review. PubMed PMID: 2434288.

17: Kane JM, Lieberman J. The efficacy of amoxapine, maprotiline, and trazodone in comparison to imipramine and amitriptyline: a review of the literature. Psychopharmacol Bull. 1984 Spring;20(2):240-9. Review. PubMed PMID: 6374720.

18: Langer SZ, Raisman R. Binding of [3H]imipramine and [3H]desipramine as biochemical tools for studies in depression. Neuropharmacology. 1983 Mar;22(3 Spec No):407-13. Review. PubMed PMID: 6304558.

19: Langer SZ, Zarifian E, Briley M, Raisman R, Sechter D. High-affinity 3H-imipramine binding: a new biological marker in depression. Pharmacopsychiatria. 1982 Jan;15(1):4-10. Review. PubMed PMID: 7038720.

20: Rogers SC, Clay PM. A statistical review of controlled trials of imipramine and placebo in the treatment of depressive illnesses. Br J Psychiatry. 1975 Dec;127:599-603. Review. PubMed PMID: 1104034.