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MedKoo Cat#: 329841 | Name: Pirlindole free base
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Description:

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

Pirlindole is a reversible inhibitor of monoamine oxidase A (RIMA) which was developed and is used in Russia as an antidepressant. It is structurally and pharmacologically related to metralindole. Pirlindole is approved in some European and non-European countries for the treatment of depression. Pirlindole has an absolute bioavailability of between 20 and 30% due to an extensive first-pass effect. Orally, the Tmax varies between 2.5 and 6 h in the rat and 0.8 and 2 h in the dog.

Chemical Structure

Pirlindole free base
Pirlindole free base
CAS#60762-57-4 (free base)

Theoretical Analysis

MedKoo Cat#: 329841

Name: Pirlindole free base

CAS#: 60762-57-4 (free base)

Chemical Formula: C15H18N2

Exact Mass: 226.1470

Molecular Weight: 226.32

Elemental Analysis: C, 79.61; H, 8.02; N, 12.38

Price and Availability

Size Price Availability Quantity
10mg USD 475.00
25mg USD 725.00
50mg USD 1,100.00
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Related CAS #
16154-78-2 (HCl) 60762-57-4 (free base) 292039-20-4 (lactate)
Synonym
Pirlindole. Lifril, Pyrazidol,
IUPAC/Chemical Name
2,3,3a,4,5,6-Hexahydro-8-methyl-1H-pyrazino(3,2,1-jk)carbazole
InChi Key
IWVRVEIKCBFZNF-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H18N2/c1-10-5-6-14-12(9-10)11-3-2-4-13-15(11)17(14)8-7-16-13/h5-6,9,13,16H,2-4,7-8H2,1H3
SMILES Code
CC1=CC2=C(C=C1)N3C4=C2CCCC4NCC3
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
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
Product Data
Instruction
View handling instruction
Biological target:
Pirlindole is a selective and reversible MAO-A inhibitor.
In vitro activity:
Rat hippocampal or cortical cultured cells were exposed either to 2 microM FeSO(4) alone or in the presence of PIR (pirlindole), DHP, BRO, DPR, MCL or TRO. PIR, DHP and TRO significantly protected cultures (P<0.05) against Fe(2+)-induced toxicity in a concentration-dependent manner. The EC(50s) of these compounds were 6, 12 and 19 microM, respectively, in hippocampal cells. For cortical cell cultures incubated in the presence of iron and PIR or DHP, EC(50s) were 5 and 6 microM respectively. All Hill coefficients were close to unity. BRO, MCL and DPR were not protective in any type of culture. The IC(50s) for the inhibition of MAO-A were 2, 2 and 0.2 microM for PIR, DHP and BRO, respectively. PIR, DHP and TRO, but not DPR, induced a significant decrease in both intracellular peroxide production and lipoperoxidation. They also improved mitochondrial function. These experiments show that PIR and DHP can protect hippocampal and cortical neurons against oxidative stress at pharmacologically relevant concentrations. Reference: Br J Pharmacol. 2002 Feb;135(3):713-20. https://pubmed.ncbi.nlm.nih.gov/11834619/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMF 1.0 4.42
DMSO 5.0 22.09
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 226.32 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:
Boland A, Gérardy J, Mossay D, Delapierre D, Seutin V. Pirlindole and dehydropirlindole protect rat cultured neuronal cells against oxidative stress-induced cell death through a mechanism unrelated to MAO-A inhibition. Br J Pharmacol. 2002 Feb;135(3):713-20. doi: 10.1038/sj.bjp.0704519. PMID: 11834619; PMCID: PMC1573183.
In vitro protocol:
Boland A, Gérardy J, Mossay D, Delapierre D, Seutin V. Pirlindole and dehydropirlindole protect rat cultured neuronal cells against oxidative stress-induced cell death through a mechanism unrelated to MAO-A inhibition. Br J Pharmacol. 2002 Feb;135(3):713-20. doi: 10.1038/sj.bjp.0704519. PMID: 11834619; PMCID: PMC1573183.
In vivo protocol:
TBD
1: Li D, Zhang L. Structure Prediction and Potential Inhibitors Docking of Enterovirus 2C Proteins. Front Microbiol. 2022 Apr 29;13:856574. doi: 10.3389/fmicb.2022.856574. PMID: 35572704; PMCID: PMC9100428. 2: Fasipe OJ. The emergence of new antidepressants for clinical use: Agomelatine paradox versus other novel agents. IBRO Rep. 2019 Jan 9;6:95-110. doi: 10.1016/j.ibror.2019.01.001. PMID: 31211282; PMCID: PMC6562183. 3: Kurteva VB, Shivachev BL, Nikolova RP. Spontaneous conversion of O-tosylates of 2-(piperazin-1-yl)ethanols into chlorides during classical tosylation procedure. R Soc Open Sci. 2019 Feb 13;6(2):181840. doi: 10.1098/rsos.181840. PMID: 30891294; PMCID: PMC6408397. 4: Lesniak A, Aarnio M, Diwakarla S, Norberg T, Nyberg F, Gordh T. Characterization of the binding site for d-deprenyl in human inflamed synovial membrane. Life Sci. 2018 Feb 1;194:26-33. doi: 10.1016/j.lfs.2017.12.003. Epub 2017 Dec 5. PMID: 29221756. 5: Nosengo N. Can you teach old drugs new tricks? Nature. 2016 Jun 16;534(7607):314-6. doi: 10.1038/534314a. PMID: 27306171. 6: Ulferts R, de Boer SM, van der Linden L, Bauer L, Lyoo HR, Maté MJ, Lichière J, Canard B, Lelieveld D, Omta W, Egan D, Coutard B, van Kuppeveld FJ. Screening of a Library of FDA-Approved Drugs Identifies Several Enterovirus Replication Inhibitors That Target Viral Protein 2C. Antimicrob Agents Chemother. 2016 Apr 22;60(5):2627-38. doi: 10.1128/AAC.02182-15. PMID: 26856848; PMCID: PMC4862474. 7: Calandre EP, Rico-Villademoros F, Slim M. An update on pharmacotherapy for the treatment of fibromyalgia. Expert Opin Pharmacother. 2015 Jun;16(9):1347-68. doi: 10.1517/14656566.2015.1047343. PMID: 26001183. 8: Morais M, Santos PA, Mateus-Pinheiro A, Patrício P, Pinto L, Sousa N, Pedroso P, Almeida S, Filipe A, Bessa JM. The effects of chronic stress on hippocampal adult neurogenesis and dendritic plasticity are reversed by selective MAO-A inhibition. J Psychopharmacol. 2014 Dec;28(12):1178-83. doi: 10.1177/0269881114553646. Epub 2014 Oct 14. PMID: 25315831. 9: Lyubimov SE, Ozolin DV, Ivanov PY, Melman A, Velezheva VS, Davankov VA. The use of phosphite-type ligands in the Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds. Chirality. 2014 Jan;26(1):56-60. doi: 10.1002/chir.22267. Epub 2013 Nov 22. PMID: 24272955. 10: Tort S, Urrútia G, Nishishinya MB, Walitt B. Monoamine oxidase inhibitors (MAOIs) for fibromyalgia syndrome. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD009807. doi: 10.1002/14651858.CD009807. PMID: 22513976. 11: Nag S, Lehmann L, Kettschau G, Heinrich T, Thiele A, Varrone A, Gulyas B, Halldin C. Synthesis and evaluation of [¹⁸F]fluororasagiline, a novel positron emission tomography (PET) radioligand for monoamine oxidase B (MAO-B). Bioorg Med Chem. 2012 May 1;20(9):3065-71. doi: 10.1016/j.bmc.2012.02.056. Epub 2012 Mar 3. PMID: 22436387. 12: Branco JC, Tomé AM, Cruz MR, Filipe A. Pirlindole in the treatment of depression and fibromyalgia syndrome. Clin Drug Investig. 2011 Oct 1;31(10):675-89. doi: 10.2165/11595410-000000000-00000. PMID: 21877764. 13: Gulyás B, Pavlova E, Kása P, Gulya K, Bakota L, Várszegi S, Keller E, Horváth MC, Nag S, Hermecz I, Magyar K, Halldin C. Activated MAO-B in the brain of Alzheimer patients, demonstrated by [11C]-L-deprenyl using whole hemisphere autoradiography. Neurochem Int. 2011 Jan;58(1):60-8. doi: 10.1016/j.neuint.2010.10.013. Epub 2010 Nov 12. PMID: 21075154. 14: Macedo A, Leiria E, Filipe A. Pirlindole in the treatment of depression: a meta-analysis. Clin Drug Investig. 2011;31(1):61-71. doi: 10.2165/11586690-000000000-00000. PMID: 21053988. 15: Bun'kova KM. [Efficacy and tolerability of clomipramine, pirlindole and escitalopram in the treatment of neurotic level depression]. Zh Nevrol Psikhiatr Im S S Korsakova. 2008;108(3):29-32. Russian. PMID: 18427538. 16: Shabanov PD, Vostrikov VV, Bushkova NV, Kuzenbaeva LB, Pavlenko VP, Mokeeva EG, Tsygan VN. [Cortexin and metabolic activators in the therapy of post- abstinent syndrome]. Voen Med Zh. 2007 Feb;328(2):38-43. Russian. PMID: 17508610. 17: Iakushev AM, Iakushev MP, Sapozhkov AV. [Comparative analysis of antiarrhythmic and proarrhythmogenic effects of drugs for neuroleptanalgesia, ataralgesia, and antidepranalgesia in experimental acute myocardial infarction]. Eksp Klin Farmakol. 2006 Jul-Aug;69(4):28-31. Russian. PMID: 16995434. 18: Zarubina IV, Narmanbetova FN, Agadzhanian EF, Shabanov PD. [Efficacy of bemithyl and pyrazidol in patients with cerebroasthenia due to brain injury]. Klin Med (Mosk). 2005;83(11):59-62. Russian. PMID: 16404942. 19: Spasova SA. Lechenie pirazidolom depressiĭ u bol'nykh pozhilogo vozrasta s somaticheskimi zabolevaniami [Pirasidol treatment of depression in elderly patients with somatic diseases]. Ter Arkh. 2004;76(10):32-6. Russian. PMID: 15575474. 20: Zarubina IV, Kuritsyna NA, Shabanov PD. Cerebroprotective effect of combined treatment with pyrazidol and bemitil in craniocerebral trauma. Bull Exp Biol Med. 2004 Jul;138(1):58-62. doi: 10.1023/b:bebm.0000046939.59393.ac. PMID: 15514724.