41100-52-1 Usage
Description
Memantine HCl, also known as Memantine Hydrochloride, is a hydrochloride form of the neuroprotective drug Memantine. It is a low to moderate affinity uncompetitive NMDA receptor antagonist that selectively binds to the NMDA receptor-operated cation channels. Memantine HCl has been clinically approved by the US FDA and European authorities for the treatment of Alzheimer's disease. It is known for its ability to suppress the misfolded mutant proteins, such as β-amyloid peptide, which are involved in the development of Alzheimer's disease. Memantine HCl is also under investigation for potential treatments for other neurodegenerative disorders, including HIV-associated dementia, neuropathic pain, glaucoma, depression, Huntington's disease, ALS, and movement disorders.
Uses
Used in Pharmaceutical Industry:
Memantine HCl is used as a pharmaceutical secondary standard for application in quality control. It provides pharmaceutical laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Used in Alzheimer's Treatment:
Memantine HCl is used as an anti-Alzheimer's agent for reducing abnormal activity in the brain. It helps patients suffering from dementia by assisting them to think more clearly and perform their daily chores with ease.
Used in Antiparkinsonian Applications:
Memantine HCl is used as an antiparkinsonian and antispasmodic agent. It acts as a dopaminergic agonist, providing relief from the symptoms of Parkinson's disease.
Used in Neurodegenerative Disorder Research:
Memantine HCl is used as a test compound to determine the dynamic range and selectivity of retinal pigment epithelium tissue penetration. It is also used as a media supplement to serve as a control to study the neuroprotective effects of erythropoietin in N-methyl-D-aspartate receptor-induced toxicity. Additionally, it is used to intraperitoneally inject experimental animals to study its effect on traumatic injury.
Used in Drug Delivery Systems:
Memantine HCl is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for Memantine HCl delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Brand Name:
The brand name for Memantine HCl is Namenda, which is marketed by Forest Laboratories in collaboration with Merz Pharmaceuticals. It was approved for the treatment of Alzheimer's disease in the US in October 2003 and is available in many European and Asian markets.
References
Reisberg, Barry, et al. New England Journal of Medicine 348.14 (2003): 1333-1341.
Lipton, Stuart A. Nature reviews Drug discovery 5.2 (2006): 160-170.
References
1) Chen and Lipton (1997), Mechanism of memantine block of NMDA-activated channels in rat retinal ganglion cells: uncompetitive antagonism; J. Physiol. 499 27
2) Chen et al. (1998), Neuroprotective concentrations of the N-methyl-D-aspartate open-channel blocker memantine are effective without cytoplasmic vacuolation following post-ischemic administration and do not block maze learning or long-term potentiation; Neuroscience 86 1121
3) Lipton et al. (2005), The molecular basis of memantine action in Alzheimer’s disease and other neurologic disorders: low-affinity, uncompetitive antagonism; Curr. Alzheimer. Res. 2 155
4) Parsons et al. (1999), Memantine is a clinically well tolerated N-methyl-D-aspartate (NMDA) receptor antagonist—a review of preclinical data; Neuropharmacology 38 735
5) Witt et al. (2004), Memantine hydrochloride; Nat. Rev. Drug Discov. 3 109
Biochem/physiol Actions
Memantine is effective against Alzheimer′s disease and Parkinson′s disease. It is also useful in treating epilepsy, motor neurone disease and trauma.
Synthesis
Memantine (XV) or 1-amino-
3,5-dimethyladamantane hydrochloride was first synthesized
by Lilly as an anti-diabetic agent but was ineffective in
lowering blood sugar. Several syntheses have been
detailed in the literature. However the simplest
synthesis of the drug was done in one step from the
commercially available 3,5-dimethyl adamantine (122).
Treatment of 122 with nitrogen trichloride (CAUTION: very
explosive gas!) in the presence of aluminum trichloride (ratio
of 1.5:1.2) gave the desired amino adamantine in 86% yield.
However, a much safer alternative has been reported by Lilly
scientists. Heating the commercially available 3,5-dimethyladamantane 122 in bromine gave the bromo
derivative 123 (86%) which was then reacted with sulfuric
acid in acetonitrile to provide quantitatively acetyl amino
derivative 124 after aqueous workup. Hydrolysis of the
acetyl group was done by heating 124 with sodium
hydroxide in diethylene glycol to give 1-amino -3,5-
adamantane (96%), which was then made into the
hydrochloride salt in ether and recrystallized from ether and
alcohol mixture to provide the final product memantine
hydrochoride XV.
Check Digit Verification of cas no
The CAS Registry Mumber 41100-52-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,1,0 and 0 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 41100-52:
(7*4)+(6*1)+(5*1)+(4*0)+(3*0)+(2*5)+(1*2)=51
51 % 10 = 1
So 41100-52-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H21N.ClH/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10;/h9H,3-8,13H2,1-2H3;1H
41100-52-1Relevant articles and documents
Preparation method of 3,5-dimethyladamantanamine hydrochloride
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Paragraph 0032-0047, (2021/12/07)
The invention discloses a preparation method of 3,5-dimethyl adamantanamine hydrochloride. The method comprises the following steps: adding 1-nitro-3,5-dimethyladamantane into a first solvent, and carrying out hydrogenation reaction in the presence of a catalyst; desolventizing the hydride material, adding water, and distilling with water vapor; extracting the distillate with a second solvent, adding hydrochloric acid, performing azeotropic dehydration, and performing crystallization separation to prepare the 3,5-dimethyladamantanamine hydrochloride. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, high yield, good product quality and easy realization of industrial production.
Preparation method of medicine for treating neurological function diseases
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Paragraph 0022; 0025-0026; 0029-0030; 0033-0034; 0037-0038, (2020/11/23)
The invention discloses a preparation method of a medicine for treating neurological function diseases, which comprises the following steps: 1) adding 1-bromo-3,5-dimethyl adamantane, acetonitrile, acatalyst 1 and a catalyst 2 into a reaction kettle, stirring to react, adding a certain amount of water into the reaction solution, cooling to precipitate a solid, adding the solid into a certain proportion of an alcohol water solution, and carrying out hot melting and cold precipitation to obtain 1-acetamido-1,3-dimethyl adamantane; and (2) carrying out high-temperature reaction on 1-acetamido-1,3-dimethyl adamantane and sodium hydroxide in ethylene glycol, adding a certain amount of purified water, extracting by adopting dichloromethane, concentrating under reduced pressure, adding an ethylacetate hydrochloride solution into the concentrated solution, cooling to allow crystal growing, carrying out suction filtration, and drying to obtain memantine hydrochloride. According to the method,the catalyst 1 and the catalyst 2 are used as reaction catalysts, so that the operation risk caused by the use of concentrated sulfuric acid is avoided, the reaction time is shortened, and the side reaction is reduced. The post-treatment is simple, the reaction yield is high, and the product purity is good.
Memantine hydrochloride synthesis method
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, (2020/03/09)
The invention provides a memantine hydrochloride synthesis method, and belongs to the technical field of medicine synthesis. The preparation method comprises the following steps: carrying out a substitution reaction on 1-bromo-3,5-dimethyladamantane and acetamide to obtain 1-acetamido-3,5-dimethyladamantane, mixing the 1-acetamido-3,5-dimethyladamantane, an alcohol and an alkali, carrying out an alcoholysis reaction to obtain 1-amino-3,5-dimethyladamantane, and finally carrying out an acidification reaction on the 1-amino-3,5-dimethyladamantane and hydrochloric acid to obtain memantine hydrochloride. According to the method of the invention, 1-bromo-3,5-dimethyl adamantane and acetamide are used as the starting raw materials, so the sources of the raw materials are wide, the use of acetonitrile is avoided, and no pollution is caused to the human body and the environment; the use of catalysts is avoided in the whole reaction process, the reaction product is easy to separate, and the yield of the obtained memantine hydrochloride is high; and the method is mild in reaction condition and suitable for industrial production.