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MedKoo Cat#: 525631 | Name: Minaprine

Description:

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

Minaprine is an antidepressant that was used the treatment of depression. A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats. In a study it has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates.

Chemical Structure

Minaprine
Minaprine
CAS#25905-77-5 (free base)

Theoretical Analysis

MedKoo Cat#: 525631

Name: Minaprine

CAS#: 25905-77-5 (free base)

Chemical Formula: C17H22N4O

Exact Mass: 298.1794

Molecular Weight: 298.39

Elemental Analysis: C, 68.43; H, 7.43; N, 18.78; O, 5.36

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Related CAS #
25953-17-7 (2HCl) 25905-77-5 (free base)
Synonym
Cantor; Minaprina; Minaprinum; CB30038; CB-30038; CB 30038; Minaprine
IUPAC/Chemical Name
4-methyl-N-(2-morpholinoethyl)-6-phenylpyridazin-3-amine
InChi Key
LDMWSLGGVTVJPG-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20)
SMILES Code
CC1=CC(C2=CC=CC=C2)=NN=C1NCCN3CCOCC3
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
Product Data
Instruction
View handling instruction
Biological target:
Minaprine is a reversible inhibitor of MAO-A.
In vitro activity:
The antidepressant, minaprine, did not modify the basal release of [3H]ACh but it antagonised the inhibitory effect of TFMPP on the K+-evoked release. The maximal reversal was found at 0.3 microM minaprine. These results suggest that minaprine interacts with heterologous presynaptic 5-HT1B receptors. Reference: Eur J Pharmacol. 1989 Sep 1;168(1):87-92. https://pubmed.ncbi.nlm.nih.gov/2583235/
In vivo activity:
The present experiments show that either repeated stress (120 min restraint daily for 10 consecutive days) or subchronic treatment with the antidepressant minaprine (5 mg/kg daily for 10 consecutive days) significantly reduced the inhibitory effect of 120 min of restraint on climbing, a behavioral response dependent on mesolimbic DA functioning. Chronic stressful experience (13 days of food restriction) and repeated amphetamine (2.5 mg/kg daily for 10 consecutive days) were as effective as subchronic minaprine in reducing immobility in the Porsolt's swimming test. However, whilst both stress and amphetamine enhanced struggling, minaprine promoted swimming. Reference: Psychopharmacology (Berl). 1995 Sep;121(1):73-80. https://pubmed.ncbi.nlm.nih.gov/8539343/
Solvent mg/mL mM comments
Solubility
DMSO 54.5 182.65
Ethanol 4.0 13.41
Water 74.0 248.00
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 298.39 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. Bolanos F, Fillion G. Minaprine antagonises the serotonergic inhibitory effect of trifluoromethylphenylpiperazine (TFMPP) on acetylcholine release. Eur J Pharmacol. 1989 Sep 1;168(1):87-92. doi: 10.1016/0014-2999(89)90636-5. PMID: 2583235. 2. Cabib S, Zocchi A, Puglisi-Allegra S. A comparison of the behavioral effects of minaprine, amphetamine and stress. Psychopharmacology (Berl). 1995 Sep;121(1):73-80. doi: 10.1007/BF02245593. PMID: 8539343. 3. Piao Y, Mineshita S, Kuroiwa T, Koike Y. Prevention by minaprine of ischemic neuronal damage and memory impairment in Mongolian gerbils. Nihon Shinkei Seishin Yakurigaku Zasshi. 1995 Apr;15(2):157-63. PMID: 7796320.
In vitro protocol:
1. Bolanos F, Fillion G. Minaprine antagonises the serotonergic inhibitory effect of trifluoromethylphenylpiperazine (TFMPP) on acetylcholine release. Eur J Pharmacol. 1989 Sep 1;168(1):87-92. doi: 10.1016/0014-2999(89)90636-5. PMID: 2583235.
In vivo protocol:
1. Cabib S, Zocchi A, Puglisi-Allegra S. A comparison of the behavioral effects of minaprine, amphetamine and stress. Psychopharmacology (Berl). 1995 Sep;121(1):73-80. doi: 10.1007/BF02245593. PMID: 8539343. 2. Piao Y, Mineshita S, Kuroiwa T, Koike Y. Prevention by minaprine of ischemic neuronal damage and memory impairment in Mongolian gerbils. Nihon Shinkei Seishin Yakurigaku Zasshi. 1995 Apr;15(2):157-63. PMID: 7796320.
1: Edwards JG, Dinan TG, Waller DG, Greentree SG. Double-blind comparative study of the antidepressant, unwanted and cardiac effects of minaprine and amitriptyline. Br J Clin Pharmacol. 1996 Oct;42(4):491-8. PubMed PMID: 8904622; PubMed Central PMCID: PMC2042690. 2: Jouglard J, Perringue C, Goujard J, Servetti A, David JM. [Evaluation by poison control centers of minaprine from the modification of tablet dosages]. Therapie. 1996 Sep-Oct;51(5):582-5. French. PubMed PMID: 9138401. 3: Allain H, Belliard S, Lieury A, Menard G, Patat A, Le Coz F, Gandon JM. [Randomized double-blind comparative study of minaprine (200mg/j) and of placebo on memory loss]. Therapie. 1996 Mar-Apr;51(2):155-62. French. PubMed PMID: 8763050. 4: Cabib S, Zocchi A, Puglisi-Allegra S. A comparison of the behavioral effects of minaprine, amphetamine and stress. Psychopharmacology (Berl). 1995 Sep;121(1):73-80. PubMed PMID: 8539343. 5: Piao Y, Mineshita S, Kuroiwa T, Koike Y. Prevention by minaprine of ischemic neuronal damage and memory impairment in Mongolian gerbils. Nihon Shinkei Seishin Yakurigaku Zasshi. 1995 Apr;15(2):157-63. PubMed PMID: 7796320. 6: Salzmann E, Robin JL. Multicentric double-blind study comparing efficacy and safety of minaprine and imipramine in dysthymic disorders. Neuropsychobiology. 1995;31(2):68-75. PubMed PMID: 7760988. 7: Sansone M, Battaglia M, Vetulani J. Minaprine, but not oxiracetam, prevents desipramine-induced impairment of avoidance learning in mice. Pol J Pharmacol. 1995 Jan-Feb;47(1):69-73. PubMed PMID: 7550552. 8: Imperato A, Obinu MC, Cabib S, Cestari V, Puglisi-Allegra S. Effects of subchronic minaprine on dopamine release in the ventral striatum and on immobility in the forced swimming test. Neurosci Lett. 1994 Jan 17;166(1):69-72. PubMed PMID: 8190361. 9: Chaki S, Muramatsu M, Otomo S. Involvement of protein kinase C activation in regulation of acetylcholine release from rat hippocampal slices by minaprine. Neurochem Int. 1994 Jan;24(1):37-41. PubMed PMID: 8130734. 10: Puglisi-Allegra S, Cabib S, Cestari V, Castellano C. Post-training minaprine enhances memory storage in mice: involvement of D1 and D2 dopamine receptors. Psychopharmacology (Berl). 1994 Jan;113(3-4):476-80. PubMed PMID: 7862862. 11: Kinirons MT, Jackson SH, Kalra L, Trevit RT, Swift CG. Computerised psychomotor performance testing: a comparative study of the single dose pharmacodynamics of minaprine and amitriptyline in young and elderly subjects. Br J Clin Pharmacol. 1993 Oct;36(4):376-9. PubMed PMID: 12959320; PubMed Central PMCID: PMC1364695. 12: Lorenzini CA, Baldi E, Bucherelli C, Tassoni G. Minaprine facilitates acquisition and retrieval of an active avoidance response in the rat. Pharmacol Biochem Behav. 1993 Jun;45(2):481-5. PubMed PMID: 8327555. 13: Bastion Y, Vial T, Espinouse D, Viala JJ, Coiffier B. [Three cases of acute agranulocytosis: caused by minaprine?]. Presse Med. 1993 Jan 23;22(2):82-3. French. PubMed PMID: 8098526. 14: Kodama K, Shibata S, Ueki S. Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. PubMed PMID: 1361012. 15: Wheatley D. Minaprine in depression. A controlled trial with amitriptyline. Br J Psychiatry. 1992 Jul;161:113-5. PubMed PMID: 1638306. 16: Karasawa Y, Araki H, Otomo S. Cholinomimetic activity of minaprine is related to the amelioration of delayed neuronal death in gerbils. Physiol Behav. 1992 Jul;52(1):141-7. PubMed PMID: 1528997. 17: Ambrogi Lorenzini C, Baldi E, Bucherelli C, Tassoni G. Minaprine cancels scopolamine effects on the rat's acquisition of passive avoidance responses in two multitrial paradigms. Pharmacol Biochem Behav. 1992 Apr;41(4):715-8. PubMed PMID: 1594638. 18: Marre F, Fabre G, Lacarelle B, Bourrie M, Catalin J, Berger Y, Rahmani R, Cano JP. Involvement of the cytochrome P-450IID subfamily in minaprine 4-hydroxylation by human hepatic microsomes. Drug Metab Dispos. 1992 Mar-Apr;20(2):316-21. PubMed PMID: 1352227. 19: Davi H, Bonnet JM, Berger Y. Disposition of minaprine in animals and in human extensive and limited debrisoquine hydroxylators. Xenobiotica. 1992 Feb;22(2):171-84. PubMed PMID: 1632106. 20: Montgomery SA, Baldwin DS, Priest RG, Steinert J, Patel A, Herrington RN, Livingston HM. Minaprine and dose response in depression. An investigation of two fixed doses of minaprine compared with imipramine. Pharmacopsychiatry. 1991 Sep;24(5):168-74. PubMed PMID: 1775522.