Ladostigil hydrochloride

• CAT Number: I041831
• CAS Number: 209394-18-3
• Molecular Formula: C16H21ClN2O2
• Molecular Weight: 308.80
• Purity: ≥95%
• Synonyms: [(3R)-3-(prop-2-ynylamino)-2,3-dihydro-1H-inden-5-yl] N-ethyl-N-methylcarbamate;hydrochloride
• InChI: InChI=1S/C16H20N2O2.ClH/c1-4-10-17-15-9-7-12-6-8-13(11-14(12)15)20-16(19)18(3)5-2;/h1,6,8,11,15,17H,5,7,9-10H2,2-3H3;1H/t15-;/m1./s1
• InChIKey: PGISQOONVUOMIG-XFULWGLBSA-N
• SMILES: CCN(C)C(=O)OC1=CC2=C(CCC2NCC#C)C=C1.Cl

Ladostigil (TV-3326) hydrochloride is an orally active dual inhibitor of cholinesterase and brain-selective monoamine oxidase (MAO), with IC50s of 37.1 and 31.8 μM for MAO-B and AChE, respectively. Ladostigil hydrochloride exhibits neuroprotective, antioxidant and anti-inflammatory activities. Ladostigil can be used for the research of depression and Alzheimer’s disease[1][2]. Ladostigil (hydrochloride) is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Ladostigil (1-10 µM) hydrochloride exerts neuroprotective activities, including a prevention of the fall of the mitochondrial membrane potential (ψ), attenuation of apoptotic cascades and an inhibition of ROS production induced by OS insults[2].
Ladostigil (1-10 µM) hydrochloride has a significant neuroprotective activity, including inhibition of caspase-3 activation, induction of Bcl-2 and reduction of Bad and Bax gene and protein expression in human neuroblastoma SK-N-SH cells[2].
Ladostigil (17 mg/kg; p.o. daily for 6 weeks) hydrochloride abolishes their hyperanxiety and depressive-like behaviour in the elevated plus maze (EPM) and forced swim tests (FST) tests in adulthood from puberty to prenatally-stressed rats[4].
Ladostigil (50 μmol/kg; single p.o.) hydrochloride restores the loss of episodic memory in the object recognition test in rats[3].

Reference

[1]. Denya I, et, al. Design, synthesis and evaluation of indole derivatives as multifunctional agents against Alzheimer’s disease. Medchemcomm. 2018 Jan 16; 9(2):357-370.
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[2]. Weinreb O, et, al. Ladostigil: a novel multimodal neuroprotective drug with cholinesterase and brain-selective monoamine oxidase inhibitory activities for Alzheimer’s disease treatment. Curr Drug Targets. 2012 Apr; 13(4): 483-94.
 [Content Brief]

[3]. Weinstock M, et, al. Ladostigil, a novel multifunctional drug for the treatment of dementia co-morbid with depression. J Neural Transm Suppl. 2006; (70):443-6.
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[4]. Poltyrev T, et, al. Effect of chronic treatment with ladostigil (TV-3326) on anxiogenic and depressive-like behaviour and on activity of the hypothalamic-pituitary-adrenal axis in male and female prenatally stressed rats. Psychopharmacology (Berl). 2005 Aug;181(1): 118-25.
 [Content Brief]