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MedKoo Cat#: 329829 | Name: Amantadine HCl
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Description:

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

Amantadine is a drug that has U.S. Food and Drug Administration approval for use both as an antiviral and an anti-parkinsonian drug. Amantadine is a weak antagonist of the NMDA-type glutamate receptor, increases dopamine release, and blocks dopamine reuptake. Amantadine probably does not inhibit MAO enzyme. Moreover, the mechanism of its antiparkinsonian effect is poorly understood.[citation needed] The drug has many effects in the brain, including release of dopamine and norepinephrine from nerve endings. It appears to be a weak NMDA receptor antagonist as well as an anticholinergic, specifically a nicotinic alpha-7 antagonist like the similar pharmaceutical memantine.

Chemical Structure

Amantadine HCl
Amantadine HCl
CAS#665-66-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 329829

Name: Amantadine HCl

CAS#: 665-66-7 (HCl)

Chemical Formula: C10H18ClN

Exact Mass: 0.0000

Molecular Weight: 187.71

Elemental Analysis: C, 63.99; H, 9.67; Cl, 18.89; N, 7.46

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
768-94-5 (free base) 665-66-7 (HCl) 31377-23-8 (sulfate)
Synonym
ADS-5102; EXP 105-1; EXP-105-1; GP 38026; Influenol; Midantan; Midantane; Mydantane; NSC 83653; Amantadine HCl; Symadine; Symmetrel; Trivaline; Virasol; Viregyt; Virofral; Virosol.
IUPAC/Chemical Name
adamantan-1-amine hydrochloride
InChi Key
WOLHOYHSEKDWQH-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H
SMILES Code
NC12CC3CC(C2)CC(C3)C1.[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
More Info
Medical uses 1. Parkinson's disease: Amantadine is used to treat Parkinsons disease, as well as parkinsonism syndromes.A 2003 Cochrane review concluded evidence was inadequate to support the use of amantadine for Parkinson's disease. An extended relief formulation is used to treat dyskinesia, a side effect of levodopa which is taken by people who have Parkinsons. 2. Influenza: Amantadine is no longer recommended for treatment of influenza A infection. For the 2008/2009 flu season, the CDC found that 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to adamantanes. The CDC issued an alert to doctors to prescribe the neuraminidase inhibitors oseltamivir and zanamivir instead of amantadine and rimantadine for treatment of flu.[6][7] A 2014 Cochrane review did not find benefit for the prevention or treatment of influenza A. 3. Fatigue in multiple sclerosis: Amantadine also seems to have moderate effects on multiple sclerosis (MS) related fatigue..
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Amantadine (1-Adamantanamine) hydrochloride is an antiviral agent with activity against influenza A viruses.
In vitro activity:
Amantadine 10–500 µM caused a concentration-dependent reduction (IC50 = 83 µM) of viral nucleic acids in the supernatant 26 h after infection (Figure 2A). In addition, in these cells intracellular viral nucleic acids were determined. Amantadine 10–500 µM caused a concentration-dependent reduction (IC50 = 119 µM) of viral nucleic acids in the cytosol 26 h after infection (Figure 2C). Reference: Viruses. 2021 Apr; 13(4): 539. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8063946/
In vivo activity:
The results obtained for the antinociceptive effect induced by the acute administration of amantadine are shown in Figure 2. Panel (a) shows that values of the control groups (Naïve and Sham) are above 14 g, which indicates that these animals did not develop hypersensitivity threshold. However, the acute administration of increasing doses of amantadine (6.25–50 mg/Kg, i.p.), but not the vehicle (0.9% NaCl, i.p.), increased (p < 0.05) in a dose-dependent manner the paw withdrawal threshold in rats with SCI (T12, 6.25 mm). Panel (b) shows that amantadine at 50 mg/Kg, i.p. dose produced 96.75% of maximum antinociceptive effect (% MPAE). In addition, an effective dose 50 (ED50) of 119.65 mmol (CI =13.59 to 37.13) was obtained. The %MPAE achieved by the intraperitoneal administration of amantadine (50 mg/Kg, i.p.) was observed from 1 hr and remained constant until 8 hr after administration, which indicates that amantadine has an antinociceptive effect until reaching similar values close to those of uninjured rats (Sham and Naïve). Reference: Eur J Pain. 2021 May 12. https://pubmed.ncbi.nlm.nih.gov/33982314/
Solvent mg/mL mM comments
Solubility
DMSO 62.7 333.86
DMF 2.0 10.65
Ethanol 21.5 114.54
PBS (pH 7.2) 5.0 26.64
Water 44.0 234.40
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 187.71 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
1: Pahwa R, Tanner CM, Hauser RA, Isaacson SH, Nausieda PA, Truong DD, Agarwal P, Hull KL, Lyons KE, Johnson R, Stempien MJ. ADS-5102 (Amantadine) Extended-Release Capsules for Levodopa-Induced Dyskinesia in Parkinson Disease (EASE LID Study): A Randomized Clinical Trial. JAMA Neurol. 2017 Aug 1;74(8):941-949. doi: 10.1001/jamaneurol.2017.0943. PubMed PMID: 28604926. 2: Czepielewski LS, Sodré L, Souza AC, Bücker J, Burke KP, Ceresér KM, Gama CS. Changes in verbal learning of patients with schizophrenia: Results from a randomized, double-blind, placebo-controlled trial of amantadine adjunctive to antipsychotics. Schizophr Res. 2015 Oct;168(1-2):571-2. doi: 10.1016/j.schres.2015.06.001. Epub 2015 Jun 21. PubMed PMID: 26104472. 3: Hammond FM, Sherer M, Malec JF, Zafonte RD, Whitney M, Bell K, Dikmen S, Bogner J, Mysiw J, Pershad R; Amantadine Irritability Multisite Study Group. Amantadine Effect on Perceptions of Irritability after Traumatic Brain Injury: Results of the Amantadine Irritability Multisite Study. J Neurotrauma. 2015 Aug 15;32(16):1230-8. doi: 10.1089/neu.2014.3803. Epub 2015 Mar 31. PubMed PMID: 25774566; PubMed Central PMCID: PMC4523042. 4: Pahwa R, Tanner CM, Hauser RA, Sethi K, Isaacson S, Truong D, Struck L, Ruby AE, McClure NL, Went GT, Stempien MJ. Amantadine extended release for levodopa-induced dyskinesia in Parkinson's disease (EASED Study). Mov Disord. 2015 May;30(6):788-95. doi: 10.1002/mds.26159. Epub 2015 Feb 4. PubMed PMID: 25650051; PubMed Central PMCID: PMC5024015. 5: Stryjer R, Budnik D, Ebert T, Green T, Polak L, Weizman S, Spivak B. Amantadine augmentation therapy for obsessive compulsive patients resistant to SSRIs-an open-label study. Clin Neuropharmacol. 2014 May-Jun;37(3):79-81. doi: 10.1097/WNF.0000000000000029. PubMed PMID: 24824662. 6: Ory-Magne F, Corvol JC, Azulay JP, Bonnet AM, Brefel-Courbon C, Damier P, Dellapina E, Destée A, Durif F, Galitzky M, Lebouvier T, Meissner W, Thalamas C, Tison F, Salis A, Sommet A, Viallet F, Vidailhet M, Rascol O; NS-Park CIC Network. Withdrawing amantadine in dyskinetic patients with Parkinson disease: the AMANDYSK trial. Neurology. 2014 Jan 28;82(4):300-7. doi: 10.1212/WNL.0000000000000050. Epub 2013 Dec 26. PubMed PMID: 24371304. 7: Hammond FM, Bickett AK, Norton JH, Pershad R. Effectiveness of amantadine hydrochloride in the reduction of chronic traumatic brain injury irritability and aggression. J Head Trauma Rehabil. 2014 Sep-Oct;29(5):391-9. doi: 10.1097/01.HTR.0000438116.56228.de. PubMed PMID: 24263176. 8: Mohammadi MR, Yadegari N, Hassanzadeh E, Farokhnia M, Yekehtaz H, Mirshafiee O, Akhondzadeh S. Double-blind, placebo-controlled trial of risperidone plus amantadine in children with autism: a 10-week randomized study. Clin Neuropharmacol. 2013 Nov-Dec;36(6):179-84. doi: 10.1097/WNF.0b013e3182a9339d. PubMed PMID: 24201232. 9: Treskatsch S, Klambeck M, Mousa SA, Kopf A, Schäfer M. Influence of high-dose intraoperative remifentanil with or without amantadine on postoperative pain intensity and morphine consumption in major abdominal surgery patients: a randomised trial. Eur J Anaesthesiol. 2014 Jan;31(1):41-9. doi: 10.1097/01.EJA.0000434967.03790.0e. PubMed PMID: 24136378. 10: Lee JY, Oh S, Kim JM, Kim JS, Oh E, Kim HT, Jeon BS, Cho JW. Intravenous amantadine on freezing of gait in Parkinson's disease: a randomized controlled trial. J Neurol. 2013 Dec;260(12):3030-8. doi: 10.1007/s00415-013-7108-7. Epub 2013 Sep 22. PubMed PMID: 24057149. 11: Raz A, Lev N, Orbach-Zinger S, Djaldetti R. Safety of perioperative treatment with intravenous amantadine in patients with Parkinson disease. Clin Neuropharmacol. 2013 Sep-Oct;36(5):166-9. doi: 10.1097/WNF.0b013e31829bd066. PubMed PMID: 24045608. 12: Seo S, Englund JA, Nguyen JT, Pukrittayakamee S, Lindegardh N, Tarning J, Tambyah PA, Renaud C, Went GT, de Jong MD, Boeckh MJ. Combination therapy with amantadine, oseltamivir and ribavirin for influenza A infection: safety and pharmacokinetics. Antivir Ther. 2013;18(3):377-86. doi: 10.3851/IMP2475. Epub 2012 Dec 21. PubMed PMID: 23264438; PubMed Central PMCID: PMC3912210. 13: Chan HF, Kukkle PL, Merello M, Lim SY, Poon YY, Moro E. Amantadine improves gait in PD patients with STN stimulation. Parkinsonism Relat Disord. 2013 Mar;19(3):316-9. doi: 10.1016/j.parkreldis.2012.11.005. Epub 2012 Dec 6. PubMed PMID: 23218842. 14: Kim YE, Yun JY, Yang HJ, Kim HJ, Gu N, Yoon SH, Cho JY, Jeon BS. Intravenous amantadine for freezing of gait resistant to dopaminergic therapy: a randomized, double-blind, placebo-controlled, cross-over clinical trial. PLoS One. 2012;7(11):e48890. doi: 10.1371/journal.pone.0048890. Epub 2012 Nov 19. PubMed PMID: 23185280; PubMed Central PMCID: PMC3501515. 15: Shaygannejad V, Janghorbani M, Ashtari F, Zakeri H. Comparison of the effect of aspirin and amantadine for the treatment of fatigue in multiple sclerosis: a randomized, blinded, crossover study. Neurol Res. 2012 Nov;34(9):854-8. doi: 10.1179/1743132812Y.0000000081. Epub 2012 Sep 12. PubMed PMID: 22979982. 16: Palabıyıkoğlu M, Ormeci N, Ekiz F, Beyler AR, Erdem H, Dökmeci A, Ozkan H, Köklü S, Coban S. Amantadine in non-responder patients with chronic hepatitis C: a randomized prospective study. Hepatogastroenterology. 2012 Sep;59(118):1911-4. doi: 10.5754/hge10341. PubMed PMID: 22819912. 17: Abbas Z, Raza S, Hamid S, Jafri W. Randomized controlled trial of interferon gamma versus amantadine in combination with interferon alpha and ribavirin for hepatitis C genotype 3 non-responders and relapsers. J Pak Med Assoc. 2012 Apr;62(4):338-43. PubMed PMID: 22755276. 18: Nissenkorn A, Hassin-Baer S, Lerman SF, Levi YB, Tzadok M, Ben-Zeev B. Movement disorder in ataxia-telangiectasia: treatment with amantadine sulfate. J Child Neurol. 2013 Feb;28(2):155-60. doi: 10.1177/0883073812441999. Epub 2012 May 1. PubMed PMID: 22550086. 19: Giacino JT, Whyte J, Bagiella E, Kalmar K, Childs N, Khademi A, Eifert B, Long D, Katz DI, Cho S, Yablon SA, Luther M, Hammond FM, Nordenbo A, Novak P, Mercer W, Maurer-Karattup P, Sherer M. Placebo-controlled trial of amantadine for severe traumatic brain injury. N Engl J Med. 2012 Mar 1;366(9):819-26. doi: 10.1056/NEJMoa1102609. PubMed PMID: 22375973. 20: Bujak-Giżycka B, Kącka K, Suski M, Olszanecki R, Madej J, Dobrogowski J, Korbut R. Beneficial effect of amantadine on postoperative pain reduction and consumption of morphine in patients subjected to elective spine surgery. Pain Med. 2012 Mar;13(3):459-65. doi: 10.1111/j.1526-4637.2011.01321.x. Epub 2012 Feb 7. PubMed PMID: 22313516.