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Rimantadine hydrochloride, an antiviral analogue of amantadine, is a white crystalline solid with potent antiviral properties. It is primarily used in the prophylaxis and treatment of influenza A, offering a lower side-effect profile compared to amantadine.

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  • 1501-84-4 Structure
  • Basic information

    1. Product Name: Rimantadine hydrochloride
    2. Synonyms: FLUMADINE;IFLAB-BB F1386-0449;MERADANE;1-(1-aminoethyl)adamantane hydrochloride;1-(1-ADAMANTYL)ETHANAMINE HYDROCHLORIDE;1-(1-ADAMANTYL)ETHYLAMINE HYDROCHLORIDE;ALPHA-METHYL-1-ADAMANTANEMETHYLAMINE HYDROCHLORIDE;ROFLUAL
    3. CAS NO:1501-84-4
    4. Molecular Formula: C12H21N*ClH
    5. Molecular Weight: 215.76
    6. EINECS: 1806241-263-5
    7. Product Categories: Adamantane derivatives;Anti-viral Compounds;Adamantanes;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals;Amine Salts;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
    8. Mol File: 1501-84-4.mol
  • Chemical Properties

    1. Melting Point: >300 °C(lit.)
    2. Boiling Point: 247.8 °C at 760 mmHg
    3. Flash Point: 99.3 °C
    4. Appearance: white crystalline solid
    5. Density: N/A
    6. Vapor Pressure: 0.0251mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: -20?C Freezer
    9. Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly), Water(Slightly)
    10. Water Solubility: Freely soluble in water.
    11. Merck: 14,8224
    12. CAS DataBase Reference: Rimantadine hydrochloride(CAS DataBase Reference)
    13. NIST Chemistry Reference: Rimantadine hydrochloride(1501-84-4)
    14. EPA Substance Registry System: Rimantadine hydrochloride(1501-84-4)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22-36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS: AU4717000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1501-84-4(Hazardous Substances Data)

1501-84-4 Usage

Uses

Used in Pharmaceutical Industry:
Rimantadine hydrochloride is used as an antiviral agent for the prevention and treatment of influenza A. Its lower side-effect profile compared to amantadine makes it a preferred choice in managing this viral infection.
Brand names:
Flumadine (Forest) and Roflual are some of the brand names under which Rimantadine hydrochloride is marketed.

Originator

DuPont (USA)

references

[1] koff w c, elm jr j l, halstead s b. suppression of dengue virus replication in vitro by rimantadine hydrochloride[j]. the american journal of tropical medicine and hygiene, 1981, 30(1): 184-189.[2] koff w c, peavy d l, knight v. inhibition of in vitro proliferative responses of human lymphocytes by rimantadine hydrochloride[j]. infection and immunity, 1979, 23(3): 665-669.[3] hayden f g, monto a s. oral rimantadine hydrochloride therapy of influenza a virus h3n2 subtype infection in adults[j]. antimicrobial agents and chemotherapy, 1986, 29(2): 339-341.

Check Digit Verification of cas no

The CAS Registry Mumber 1501-84-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,0 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1501-84:
(6*1)+(5*5)+(4*0)+(3*1)+(2*8)+(1*4)=54
54 % 10 = 4
So 1501-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H21N.ClH/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12;/h8-11H,2-7,13H2,1H3;1H

1501-84-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (R0070)  1-(1-Adamantyl)ethylamine Hydrochloride  >98.0%(N)

  • 1501-84-4

  • 5g

  • 495.00CNY

  • Detail
  • Alfa Aesar

  • (H53377)  1-(1-Adamantyl)ethylamine hydrochloride, 99%   

  • 1501-84-4

  • 5g

  • 834.0CNY

  • Detail
  • Alfa Aesar

  • (H53377)  1-(1-Adamantyl)ethylamine hydrochloride, 99%   

  • 1501-84-4

  • 25g

  • 3334.0CNY

  • Detail
  • USP

  • (1604508)  Rimantadinehydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 1501-84-4

  • 1604508-300MG

  • 4,662.45CNY

  • Detail
  • Aldrich

  • (390593)  1-(1-Adamantyl)ethylaminehydrochloride  99%

  • 1501-84-4

  • 390593-1G

  • 772.20CNY

  • Detail

1501-84-4Relevant articles and documents

Preparation method of rimantadine hydrochloride preparation

-

, (2019/02/04)

The invention discloses a preparation method of a rimantadine hydrochloride preparation. The preparation method comprises the following steps: preparation of 1-bromoadamantane, preparation of amantadecanoic acid, preparation of adamantanecarbonyl chloride, preparation of adamantyl methy ketone, preparation of 1-amantadine methyl ketone oxime, preparation of rimantadine hydrochloride, and preparation of the rimantadine hydrochloride preparation. The preparation of adamantyl methy ketone comprises the following steps: adding (CH3)3Sb and nickelous formate into a flask; dropwise adding an acetonitrile solution of adamantanecarbonyl chloride, wherein adamantanecarbonyl chloride reacts with (CH3)3Sb to generate adamantyl methy ketone; after reaction, pouring a reaction liquid into ice water; and filtering and drying the mixture to obtain a light yellow precipitate, thereby obtaining the adamantyl methy ketone. The preparation method has the beneficial effects that the preparation method ofrimantadine hydrochloride preparation is good in environmental protection, mild in condition of a synthetic method, simple and feasible in process and high in product yield.

Synthesizing method of rimantadine hydrochloride

-

, (2019/02/21)

The invention discloses a synthesizing method of rimantadine hydrochloride. The synthesizing method comprises the following steps of preparing of 1-bromoadamantane, preparing of adamantane carboxylicacid, preparing of adamantanecarbonyl chloride, preparing of adamantyl methyl ketone, preparing of 1-amantadine methyl ketone oxime, preparing of rimantadine hydrochloride, and preparing of a rimantadine hydrochloride preparation; in the preparing process of adamantyl methyl ketone: adding trimethylaluminum and cerium formate into a flask, then dripping a benzene solution of adamantanecarbonyl chloride, and enabling the adamantanecarbonyl chloride and the trimethylaluminum to react and generate adamantyl methyl ketone; after reaction is finished, pouring a reaction solution into ice water, filtering and drying, so as to obtain a light yellow precipitate, namely the adamantyl methyl ketone. The synthesizing method has the beneficial effects that the conditions are mild, and the technology is simple and feasible; the usage amount of catalyst is small, the environment-friendly effect is realized, and the yield of product is high.

A kind of anti-influenza virus preparation

-

, (2019/03/15)

The present invention discloses an anti-influenza virus preparation, including 1 - bromo adamantane preparation, adamantane formic acid preparation, adamantane chloride preparation, adamantane methyl preparation, 1 - adamantane methyl oxime preparation, hydrochloric acid rimantadine preparation, anti-influenza virus preparation, wherein the adamantane methyl preparation steps are as follows: in the flask to join the three trimethylaluminum, formic acid cerium, then dropwise adamantane formyl chloride [...], the adamantane chloride with three methyl aluminum reaction generating adamantane methyl ketone, after the reaction is completed in the reaction liquid into ice water, then filtering, drying, the resulting pale yellow precipitate adamantane methyl ketone. The beneficial effects: preparation method of this invention mild condition, the process is simple and feasible, high product yield, the system anti- influenza virus preparation can be effective prevention and treatment of type a/b influenza virus infection, also can effectively alleviate the symptoms of the common cold.

Process for preparing rimantadine

-

, (2008/06/13)

A low temperature and pressure process for preparing rimantadine in high yields from 1-adamantyl methyl ketoxime is provided. The process comprises contacting a solution of the ketoxime with hydrogen in the presence of a platinum on carbon catalyst at a low temperature and pressure, e.g., room temperature and a pressure of about 25-115 psia (170-790 KPa) are preferred.

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