Ladostigil free base

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

MedKoo CAT#: 326668

CAS#: 209349-27-4 (free base)

Description: Ladostigil, also known as TV-3326, is novel neuroprotective agent being investigated for the treatment of neurodegenerative disorders like Alzheimer's disease, Lewy body disease, and Parkinson's disease. It acts as a reversible acetylcholinesterase and butyrylcholinesterase inhibitor, and an irreversible monoamine oxidase B inhibitor, and combines the mechanisms of action of older drugs like rivastigmine and rasagiline into a single molecule. (https://en.wikipedia.org/wiki/Ladostigil).

Chemical Structure

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Ladostigil free base
CAS# 209349-27-4 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 326668
Name: Ladostigil free base
CAS#: 209349-27-4 (free base)
Chemical Formula: C16H20N2O2
Exact Mass: 272.15
Molecular Weight: 272.348
Elemental Analysis: C, 70.56; H, 7.40; N, 10.29; O, 11.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 209394-46-7 (tartrate)   209349-27-4 (free base)    

Synonym: TV-3326; TV 3326; TV3326; Ladostigil

IUPAC/Chemical Name: (R)-3-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-inden-5-yl ethyl(methyl)carbamate

InChi Key: LHXOCOHMBFOVJS-OAHLLOKOSA-N

InChi Code: InChI=1S/C16H20N2O2/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/t15-/m1/s1

SMILES Code: O=C(OC1=CC2=C(CC[C@H]2NCC#C)C=C1)N(CC)C

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: Related CAS# 209394-46-7 (Ladostigil Tartrate) 209394-27-4 (Ladostigil)

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 272.35 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:
In vitro protocol:
In vivo protocol:

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1: Bar-Am O, Amit T, Youdim MB, Weinreb O. Neuroprotective and neurorestorative potential of propargylamine derivatives in ageing: focus on mitochondrial targets. J Neural Transm (Vienna). 2016 Feb;123(2):125-35. doi: 10.1007/s00702-015-1395-3. Epub 2015 Apr 10. PubMed PMID: 25859841.

2: Moradov D, Finkin-Groner E, Bejar C, Sunita P, Schorer-Apelbaum D, Barasch D, Nemirovski A, Cohen M, Weinstock M. Dose-limiting inhibition of acetylcholinesterase by ladostigil results from the rapid formation and fast hydrolysis of the drug-enzyme complex formed by its major metabolite, R-MCPAI. Biochem Pharmacol. 2015 Mar 15;94(2):164-72. doi: 10.1016/j.bcp.2015.01.017. Epub 2015 Feb 7. PubMed PMID: 25662585.

3: Goelman G, Ilinca R, Zohar I, Weinstock M. Functional connectivity in prenatally stressed rats with and without maternal treatment with ladostigil, a brain-selective monoamine oxidase inhibitor. Eur J Neurosci. 2014 Sep;40(5):2734-43. doi: 10.1111/ejn.12621. Epub 2014 May 26. PubMed PMID: 24862938.

4: Bansal Y, Silakari O. Multifunctional compounds: smart molecules for multifactorial diseases. Eur J Med Chem. 2014 Apr 9;76:31-42. doi: 10.1016/j.ejmech.2014.01.060. Epub 2014 Jan 31. Review. PubMed PMID: 24565571.

5: Youdim MB, Kupershmidt L, Amit T, Weinreb O. Promises of novel multi-target neuroprotective and neurorestorative drugs for Parkinson's disease. Parkinsonism Relat Disord. 2014 Jan;20 Suppl 1:S132-6. doi: 10.1016/S1353-8020(13)70032-4. Review. PubMed PMID: 24262165.

6: Youdim MB. Multi target neuroprotective and neurorestorative anti-Parkinson and anti-Alzheimer drugs ladostigil and m30 derived from rasagiline. Exp Neurobiol. 2013 Mar;22(1):1-10. doi: 10.5607/en.2013.22.1.1. Epub 2013 Mar 31. PubMed PMID: 23585716; PubMed Central PMCID: PMC3620452.

7: Geldenhuys WJ, Van der Schyf CJ. Rationally designed multi-targeted agents against neurodegenerative diseases. Curr Med Chem. 2013;20(13):1662-72. Review. PubMed PMID: 23410161.

8: Weinstock M, Bejar C, Schorer-Apelbaum D, Panarsky R, Luques L, Shoham S. Dose-dependent effects of ladostigil on microglial activation and cognition in aged rats. J Neuroimmune Pharmacol. 2013 Mar;8(1):345-55. doi: 10.1007/s11481-013-9433-0. Epub 2013 Jan 17. PubMed PMID: 23325108.

9: Al-Nuaimi SK, Mackenzie EM, Baker GB. Monoamine oxidase inhibitors and neuroprotection: a review. Am J Ther. 2012 Nov;19(6):436-48. doi: 10.1097/MJT.0b013e31825b9eb5. Review. PubMed PMID: 22960850.

10: Panarsky R, Luques L, Weinstock M. Anti-inflammatory effects of ladostigil and its metabolites in aged rat brain and in microglial cells. J Neuroimmune Pharmacol. 2012 Jun;7(2):488-98. doi: 10.1007/s11481-012-9358-z. Epub 2012 Mar 28. PubMed PMID: 22454040.

11: Weinreb O, Amit T, Bar-Am O, Youdim MB. 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. Review. PubMed PMID: 22280345.

12: Weinreb O, Amit T, Bar-Am O, Youdim MB. A novel anti-Alzheimer's disease drug, ladostigil neuroprotective, multimodal brain-selective monoamine oxidase and cholinesterase inhibitor. Int Rev Neurobiol. 2011;100:191-215. doi: 10.1016/B978-0-12-386467-3.00010-8. Review. PubMed PMID: 21971009.

13: Patyar S, Prakash A, Medhi B. Dual inhibition: a novel promising pharmacological approach for different disease conditions. J Pharm Pharmacol. 2011 Apr;63(4):459-71. doi: 10.1111/j.2042-7158.2010.01236.x. Epub 2011 Mar 1. Review. PubMed PMID: 21401597.

14: Bar-Am O, Amit T, Weinreb O, Youdim MB, Mandel S. Propargylamine containing compounds as modulators of proteolytic cleavage of amyloid-beta protein precursor: involvement of MAPK and PKC activation. J Alzheimers Dis. 2010;21(2):361-71. doi: 10.3233/JAD-2010-100150. Review. PubMed PMID: 20555137.

15: Weinstock M, Luques L, Poltyrev T, Bejar C, Shoham S. Ladostigil prevents age-related glial activation and spatial memory deficits in rats. Neurobiol Aging. 2011 Jun;32(6):1069-78. doi: 10.1016/j.neurobiolaging.2009.06.004. Epub 2009 Jul 21. PubMed PMID: 19625104.

16: Bolognesi ML, Matera R, Minarini A, Rosini M, Melchiorre C. Alzheimer's disease: new approaches to drug discovery. Curr Opin Chem Biol. 2009 Jun;13(3):303-8. doi: 10.1016/j.cbpa.2009.04.619. Epub 2009 May 19. Review. PubMed PMID: 19467915.

17: Liu RT, Lü QJ. [Progress in the research on multi-target-directed drugs against Alzheimer's disease]. Yao Xue Xue Bao. 2009 Mar;44(3):258-63. Review. Chinese. PubMed PMID: 19449521.

18: Weinreb O, Mandel S, Bar-Am O, Yogev-Falach M, Avramovich-Tirosh Y, Amit T, Youdim MB. Multifunctional neuroprotective derivatives of rasagiline as anti-Alzheimer's disease drugs. Neurotherapeutics. 2009 Jan;6(1):163-74. doi: 10.1016/j.nurt.2008.10.030. Review. PubMed PMID: 19110207.

19: Bar-Am O, Weinreb O, Amit T, Youdim MB. The novel cholinesterase-monoamine oxidase inhibitor and antioxidant, ladostigil, confers neuroprotection in neuroblastoma cells and aged rats. J Mol Neurosci. 2009 Feb;37(2):135-45. doi: 10.1007/s12031-008-9139-6. Epub 2008 Aug 27. PubMed PMID: 18751929.

20: Weinreb O, Bar-Am O, Amit T, Drigues N, Sagi Y, Youdim MB. The neuroprotective effect of ladostigil against hydrogen peroxide-mediated cytotoxicity. Chem Biol Interact. 2008 Sep 25;175(1-3):318-26. doi: 10.1016/j.cbi.2008.05.038. Epub 2008 Jun 12. PubMed PMID: 18598687.