112668-45-8

Basic information

• Product Name: 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol
• Synonyms: 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol;2-Hydroxy IMiquiMod;Imiquimod Impurity 1
• CAS NO: 112668-45-8
• Molecular Formula: C14H16N4O
• Molecular Weight: 256.30304
• Mol File: 112668-45-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 513.6°C at 760 mmHg
• Flash Point: 264.4°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 2.26E-11mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol(112668-45-8)
• EPA Substance Registry System: 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol(112668-45-8)

Safety Data

• Hazardous Substances Data: 112668-45-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H16N4O/c1-14(2,19)7-18-8-16-11-12(18)9-5-3-4-6-10(9)17-13(11)15/h3-6,8,19H,7H2,1-2H3,(H2,15,17)

Upstream product

• 1375262-91-1 5-(2-aminophenyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile 
• 1375262-89-7 5-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile 
• 200198-35-2 α,α-Dimethyl-6H-imidazo [4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol 
• 95-50-1 1,2-dichloro-benzene 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 
• 15151-57-2 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one 
• 133860-77-2 1-[(2-chloro-3-nitro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 133860-78-3 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 129655-65-8 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline 

Relevant articles and documents

Discovery of imidazoquinolines with toll-like receptor 7/8 independent cytokine induction

Toll-like receptors (TLRs) are key targets in the design of immunomodulating agents for use as vaccine adjuvants and anticancer treatments. The imidazoquinolines, imiquimod and resiquimod, have been shown to activate TLR-7 and -8, which in turn induce cytokine production as part of the innate immune response. Herein, we report the synthesis and discovery of a C7-methoxycarbonyl derivative of imiquimod that stimulates cytokine production but is devoid of TLR-7/8 activity. Data are presented that shows that this analogue not only induces IL-12p40 and TNF production, similar to that of imiquimod and resiquimod, but greatly enhances the production of IL-1β, a key cytokine involved in the activation of CD4 T cells. It is further demonstrated that TLR-7/8 activation can be recovered by the addition of a C2-alkyl substituent to this newly discovered analogue. The results support the existence of an alternative mechanism of action by which imidazoquinolines can stimulate cytokine production.

Use of immidazoquinolinamines as adjuvants in dna vaccination

The present invention relates to the use of a 1H-imidazo[4,5-c]-4-amine derivative as an adjuvant for use with nucleic acid vaccination.

1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES AND ANTIVIRAL USE

1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described