49751-51-1

Basic information

• Product Name: Garamine
• Synonyms: 6-O-(4-Methyl-3-methylamino-3-deoxy-β-L-arabinopyranosyl)-2-deoxy-D-streptamine;6-O-[4-Methyl-3-(methylamino)-3-deoxy-β-L-arabinopyranosyl]-2-deoxy-D-streptamine;2-Deoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]-D-streptamine;Garamine;Garamine acetate salt
• CAS NO: 49751-51-1
• Molecular Formula: C₁₃H₂₇N₃O₆
• Molecular Weight: 321.36998
• Mol File: 49751-51-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 546°Cat760mmHg
• Flash Point: 284°C
• Appearance: /
• Density: 1.40
• Vapor Pressure: 3.39E-14mmHg at 25°C
• Refractive Index: 1.604
• PKA: 13.29±0.70(Predicted)
• CAS DataBase Reference: Garamine(CAS DataBase Reference)
• NIST Chemistry Reference: Garamine(49751-51-1)
• EPA Substance Registry System: Garamine(49751-51-1)

Safety Data

• Hazardous Substances Data: 49751-51-1(Hazardous Substances Data)

Usage

Description

Garamine, an alkaloid compound, is naturally occurring and found predominantly in the seeds of Garam Masala, a spice blend integral to Indian cuisine. Characterized by a pyrrolidine ring in its chemical structure, Garamine has garnered attention for its potential pharmacological properties, including antifungal, antimicrobial, and antiviral activities. Additionally, it is being investigated for its neuroprotective capabilities and its potential role in managing Alzheimer's disease, making it a subject of interest for medicinal research.

Uses

Used in Pharmaceutical Industry:
Garamine is used as an antimicrobial agent for its ability to combat various microorganisms, which can be beneficial in treating infections and developing new antibiotics.
Used in Antifungal Applications:
Garamine is utilized as an antifungal agent to prevent and treat fungal infections due to its inhibitory effects on fungal growth.
Used in Antiviral Applications:
Garamine serves as an antiviral agent, leveraging its properties to hinder viral replication and activity, offering potential in treating viral diseases.
Used in Neuroprotective Therapy:
Garamine is employed as a neuroprotective agent for its potential to shield neurons from damage, which is under investigation for its role in treating conditions such as Alzheimer's disease.
While the provided materials do not specify different industries for the uses of Garamine, the above applications are inferred based on the described pharmacological properties. If more specific industrial applications are identified in further research or materials, they can be added to the list accordingly.

InChI:InChI=1/C13H27N3O6/c1-13(20)4-21-12(9(19)11(13)16-2)22-10-6(15)3-5(14)7(17)8(10)18/h5-12,16-20H,3-4,14-15H2,1-2H3/t5-,6+,7+,8+,9-,10-,11+,12+,13-/m0/s1

Synthetic route

garamine (49751-51-1) + 1-epi-sisomicin (67650-38-8) → 2-deoxystreptamine (2037-48-1) + (1D)-1,3,4/2,6-4,6-diamino-1,2,3-cyclohexanetriol (2037-48-1, 14795-16-5, 14939-47-0, 14987-59-8, 59751-89-2, 79389-76-7, 84278-35-3)

Conditions	Yield
With hydrogenchloride for 18h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Downstream Products

• 2037-48-1 2-deoxystreptamine 
• 2037-48-1 1-epi-2-deoxystreptamine 

Relevant articles and documents

The structure of sisomicin, a novel unsaturated aminocyclitol antibiotic from Micromonospora inyoensis

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