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MedKoo Cat#: 125461 | Name: Pirlindole HCl

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 HCl
Pirlindole HCl
CAS#16154-78-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 125461

Name: Pirlindole HCl

CAS#: 16154-78-2 (HCl)

Chemical Formula: C15H19ClN2

Exact Mass: 262.1200

Molecular Weight: 262.78

Elemental Analysis: C, 68.56; H, 7.29; Cl, 13.49; N, 10.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
16154-78-2 (HCl) 60762-57-4 (free base) 292039-20-4 (lactate)
Synonym
Pirlindole hydrochloride; 16154-78-2; Pyrazidole; Pyrazidol; 8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole hydrochloride
IUPAC/Chemical Name
8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole hydrochloride
InChi Key
LIFOOCLGAAEVIF-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H18N2.ClH/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;1H
SMILES Code
Cl.CC1=CC=C2N3CCNC4CCCC(C2=C1)=C34
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 262.78 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
1: 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. PubMed PMID: 21053988. 2: 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. Review. PubMed PMID: 21877764. 3: Fiedler VB, Buchheim S, Nitz RE, Scholtholt J. Haemodynamic effects of pirlindole, a new tetracyclic antidepressant agent. Arzneimittelforschung. 1983;33(2):244-50. PubMed PMID: 6682664. 4: Boland A, Gérardy J, Mossay D, Seutin V. Pre- and post-treatment with pirlindole and dehydropirlindole protects cultured brain cells against nitric oxide-induced death. Eur J Pharmacol. 2003 Apr 11;466(1-2):21-30. PubMed PMID: 12679138. 5: 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. PubMed PMID: 18427538. 6: Medvedev AE, Shvedov VI, Chulkova TM, Fedotova OA, Saederup E, Squires RF. The influence of the antidepressant pirlindole and its dehydro-derivative on the activity of monoamine oxidase A and GABAA receptor binding. J Neural Transm Suppl. 1998;52:337-42. PubMed PMID: 9564636. 7: Medvedev AE, Shvedov VI, Chulkova TM, Fedotova OA, Saederup E, Squires RF. Effects of the antidepressant pirlindole and its dehydro-derivative on the activity of monoamine oxidase-A and on GABAA receptors. Neurochem Res. 1996 Dec;21(12):1521-6. PubMed PMID: 8953568. 8: Ehlers T, Ritter M. Effects of the tetracyclic antidepressant pirlindole on sensorimotor performance and subjective condition in comparison to imipramine and during interaction of ethanol. Neuropsychobiology. 1984;12(1):48-54. PubMed PMID: 6514177. 9: Bruhwyler J, Liégeois JF, Gérardy J, Damas J, Chleide E, Lejeune C, Decamp E, de Tullio P, Delarge J, Dresse A, Géczy J. Comparative study of pirlindole, a selective RIMA, and its two enantiomers using biochemical and behavioural techniques. Behav Pharmacol. 1998 Dec;9(8):731-7. PubMed PMID: 9890262. 10: Bruhwyler J, Liégeois JF, Géczy J. Pirlindole: a selective reversible inhibitor of monoamine oxidase A. A review of its preclinical properties. Pharmacol Res. 1997 Jul;36(1):23-33. Review. PubMed PMID: 9368911. 11: Ostrowski J, Theumer J, Gärtner W, Resag K, Passing H. Determination of pirlindole in plasma and urine by high-performance liquid chromatography. J Chromatogr. 1984 Jul 13;309(1):115-23. PubMed PMID: 6480758. 12: Tanghe A, Geerts S, Van Dorpe J, Brichard B, Bruhwyler J, Géczy J. Double-blind randomized controlled study of the efficacy and tolerability of two reversible monoamine oxidase A inhibitors, pirlindole and moclobemide, in the treatment of depression. Acta Psychiatr Scand. 1997 Aug;96(2):134-41. PubMed PMID: 9272198. 13: 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. PubMed PMID: 25315831. 14: Ceccato A, Hubert P, de Tullio P, Liégeois JF, Felikidis A, Géczy J, Crommen J. Enantiomeric separation of pirlindole by liquid chromatography using different types of chiral stationary phases. J Pharm Biomed Anal. 1998 Dec;18(4-5):605-14. PubMed PMID: 9919961. 15: 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. Print 2016 May. PubMed PMID: 26856848; PubMed Central PMCID: PMC4862474. 16: Nosengo N. Can you teach old drugs new tricks? Nature. 2016 Jun 16;534(7607):314-6. doi: 10.1038/534314a. PubMed PMID: 27306171. 17: De Wilde JE, Geerts S, Van Dorpe J, Bruhwyler J, Géczy J. A double-blind randomized placebo-controlled study of the efficacy and safety of pirlindole, a reversible monoamine oxidase A inhibitor, in the treatment of depression. Acta Psychiatr Scand. 1996 Dec;94(6):404-10. PubMed PMID: 9020990. 18: Hynson RM, Wouters J, Ramsay RR. Monoamine oxidase A inhibitory potency and flavin perturbation are influenced by different aspects of pirlindole inhibitor structure. Biochem Pharmacol. 2003 Jun 1;65(11):1867-74. PubMed PMID: 12781338. 19: Mashkovsky MD, Andrejeva NI. Pharmacological properties of 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino [3,2,1-j,k]carbazol hydrochloride (pirlindole), a new antidepressant. Arzneimittelforschung. 1981;31(1):75-9. PubMed PMID: 7194096. 20: Ceccato A, Hubert P, de Tullio P, Liégeois JF, Stachow M, Géczy J, Crommen J. Simultaneous determination of pirlindole enantiomers and dehydropirlindole by chiral liquid chromatography. J Pharm Biomed Anal. 1998 Sep 1;17(6-7):1071-9. PubMed PMID: 9884197.