Latrepirdine | Dimebone hydrochloride | CAS#97657-92-6 | CAS#3613-73-8

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

MedKoo CAT#: 300220

CAS#: 97657-92-6 (HCl)

Description: Latrepirdine, also known as dimebolin (sold as Dimebon), is an antihistamine drug which has been used clinically in Russia since 1983. Research is continuing in both Russia and western nations into potential applications as a neuroprotective drug to combat Alzheimer's disease and, possibly, as a nootropic as well. However, a Phase III clinical trial for Alzheimer's disease treatment failed to show any benefit. (Source: http://en.wikipedia.org/wiki/Latrepirdine)

Chemical Structure

Latrepirdine HCl

CAS# 97657-92-6 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 300220
Name: Latrepirdine HCl
CAS#: 97657-92-6 (HCl)
Chemical Formula: C21H27Cl2N3
Exact Mass: 0.00
Molecular Weight: 392.368
Elemental Analysis: C, 64.28; H, 6.94; Cl, 18.07; N, 10.71

Price and Availability

Size	Price	Availability
10mg	USD 350	2 Weeks
25mg	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 3613-73-8 (free base) 97657-92-6 (HCl)

Synonym: Latrepirdine HCl, Dimebolin HCl, Dimebon HCl,

IUPAC/Chemical Name: 2,8-dimethyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole dihydrochloride

InChi Key: GTWLIQOLGOZTLF-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H25N3.2ClH/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17;;/h4-7,12-13H,8-11,14H2,1-3H3;2*1H

SMILES Code: CC1=CC=C(CCN2C3=C(CN(C)CC3)C4=C2C=CC(C)=C4)C=N1.[H]Cl.[H]Cl

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

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Product Data:

Product Data

Instruction:

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Biological target:	Latrepirdine dihydrochloride is a neuroactive compound with antagonist activity at histaminergic, α-adrenergic, and serotonergic receptors.
In vitro activity:	The ability of latrepirdine to alter the formation of Aβ42 aggregates was assessed by thioflavin-T fluorescence, western immunoblotting and atomic force microscopy (AFM). Despite showing a reduction in thioflavin-T fluorescence with latrepirdine treatment, indicating a decrease in aggregation, immunoblotting and AFM showed a modest increase in both the formation and size of Aβ aggregates. The ability of latrepirdine to modulate Aβ aggregation appears to be independent of its neuroprotective effects, and is unlikely to be a mechanism by which latrepirdine offers protection. Reference: J Alzheimers Dis. 2016;50(3):895-905. https://pubmed.ncbi.nlm.nih.gov/26836170/
In vivo activity:	Treatment with latrepirdine increased AMPK activity in primary mouse motor neuron cultures and in SOD1(G93A) lumbar spinal cords. Mice "preconditioned" with latrepirdine showed a delayed symptom onset and a significant increase in life span (p < 0.01). Reference: Neurobiol Aging. 2015 Feb;36(2):1140-50. https://pubmed.ncbi.nlm.nih.gov/25443289/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	1.0	2.55
	DMSO	7.1	18.18
	Ethanol	6.5	16.57
	PBS (pH 7.2)	10.0	25.49
	Water	100.0	254.86

Preparing Stock Solutions

The following data is based on the product molecular weight 392.37 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.

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. Porter T, Bharadwaj P, Groth D, Paxman A, Laws SM, Martins RN, Verdile G. The Effects of Latrepirdine on Amyloid-β Aggregation and Toxicity. J Alzheimers Dis. 2016;50(3):895-905. doi: 10.3233/JAD-150790. PMID: 26836170; PMCID: PMC4927897. 2. Weisová P, Alvarez SP, Kilbride SM, Anilkumar U, Baumann B, Jordán J, Bernas T, Huber HJ, Düssmann H, Prehn JH. Latrepirdine is a potent activator of AMP-activated protein kinase and reduces neuronal excitability. Transl Psychiatry. 2013 Oct 22;3(10):e317. doi: 10.1038/tp.2013.92. PMID: 24150226; PMCID: PMC3818013. 3. Coughlan KS, Mitchem MR, Hogg MC, Prehn JH. "Preconditioning" with latrepirdine, an adenosine 5'-monophosphate-activated protein kinase activator, delays amyotrophic lateral sclerosis progression in SOD1(G93A) mice. Neurobiol Aging. 2015 Feb;36(2):1140-50. doi: 10.1016/j.neurobiolaging.2014.09.022. Epub 2014 Sep 26. PMID: 25443289. 4. Steele JW, Gandy S. Latrepirdine (Dimebon®), a potential Alzheimer therapeutic, regulates autophagy and neuropathology in an Alzheimer mouse model. Autophagy. 2013 Apr;9(4):617-8. doi: 10.4161/auto.23487. Epub 2013 Feb 4. PMID: 23380933; PMCID: PMC3627679.
In vitro protocol:	1. Porter T, Bharadwaj P, Groth D, Paxman A, Laws SM, Martins RN, Verdile G. The Effects of Latrepirdine on Amyloid-β Aggregation and Toxicity. J Alzheimers Dis. 2016;50(3):895-905. doi: 10.3233/JAD-150790. PMID: 26836170; PMCID: PMC4927897. 2. Weisová P, Alvarez SP, Kilbride SM, Anilkumar U, Baumann B, Jordán J, Bernas T, Huber HJ, Düssmann H, Prehn JH. Latrepirdine is a potent activator of AMP-activated protein kinase and reduces neuronal excitability. Transl Psychiatry. 2013 Oct 22;3(10):e317. doi: 10.1038/tp.2013.92. PMID: 24150226; PMCID: PMC3818013.
In vivo protocol:	1. Coughlan KS, Mitchem MR, Hogg MC, Prehn JH. "Preconditioning" with latrepirdine, an adenosine 5'-monophosphate-activated protein kinase activator, delays amyotrophic lateral sclerosis progression in SOD1(G93A) mice. Neurobiol Aging. 2015 Feb;36(2):1140-50. doi: 10.1016/j.neurobiolaging.2014.09.022. Epub 2014 Sep 26. PMID: 25443289. 2. Steele JW, Gandy S. Latrepirdine (Dimebon®), a potential Alzheimer therapeutic, regulates autophagy and neuropathology in an Alzheimer mouse model. Autophagy. 2013 Apr;9(4):617-8. doi: 10.4161/auto.23487. Epub 2013 Feb 4. PMID: 23380933; PMCID: PMC3627679.

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1: Vignisse J, Steinbusch HW, Bolkunov A, Nunes J, Santos AI, Grandfils C, Bachurin S, Strekalova T. Dimebon enhances hippocampus-dependent learning in both appetitive and inhibitory memory tasks in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2010 Dec 14. [Epub ahead of print] PubMed PMID: 21163318.

2: Bachurin SO, Ustyugov AA, Peters O, Shelkovnikova TA, Buchman VL, Ninkina NN. Hindering of proteinopathy-induced neurodegeneration as a new mechanism of action for neuroprotectors and cognition enhancing compounds. Dokl Biochem Biophys. 2009 Sep-Oct;428:235-8. PubMed PMID: 20848907.

3: Tabira T. [Development of new drugs for Alzheimer's disease]. Brain Nerve. 2010 Jul;62(7):787-96. Review. Japanese. PubMed PMID: 20675883.

4: Shoji M. [Drug therapy for Alzheimer's disease]. Brain Nerve. 2010 Jul;62(7):777-85. Review. Japanese. PubMed PMID: 20675882.

5: Learning from failure. Nat Rev Drug Discov. 2010 Jul;9(7):499. PubMed PMID: 20614555.

6: Zhang S, Hedskog L, Petersen CA, Winblad B, Ankarcrona M. Dimebon (latrepirdine) enhances mitochondrial function and protects neuronal cells from death. J Alzheimers Dis. 2010;21(2):389-402. PubMed PMID: 20555134.

7: Sachdeva D, Burns A. Dimebolin in Dementia. CNS Neurosci Ther. 2010 Jun 11. [Epub ahead of print] PubMed PMID: 20553307.

8: Mechanism matters. Nat Med. 2010 Apr;16(4):347. PubMed PMID: 20376007.

9: Gao M, Wang M, Hutchins GD, Zheng QH. [(11)C]Dimebon, radiosynthesis and lipophilicity of a new potential PET agent for imaging of Alzheimer's disease and Huntington's disease. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2529-32. Epub 2010 Mar 3. PubMed PMID: 20299213.

10: Miller G. Pharmacology. The puzzling rise and fall of a dark-horse Alzheimer's drug. Science. 2010 Mar 12;327(5971):1309. PubMed PMID: 20223954.

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