Хинамин

Description

Quinamine is a monoterpene indole alkaloid, a minor component of cinchona bark. It differs fundamentally from the main alkaloids of cinchona - quinine and quinidine: instead of the quinoline core, the molecule carries a condensed furo[2,3-b]indole system associated with a quinuclidine fragment. Product form - a purified standard sample for analytical and research work.

Identification

• CAS No.: 464-85-7
• Chemical formula: C19H24N2O2
• EU number: 207-357-3
• Class: monoterpene indole alkaloids
• Synonym: alkaloid B from Cinchona ledgeriana
• Full stereochemical name: (3aR,8aS)-8a-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2,2,2]oct-2-yl]-2,3,8,8a-tetrahydro-3aH-furo[2,3-b]indol-3a-ol

Basic Attributes

• Molecular Weight: 312.40606
• Exact weight: 312.41

Physico-chemical characteristics

• Melting point: 185.5 °C
• Density: 1.1209 (estimated)
• Steam pressure: 0 mmHg Art. at 25 °C
• Specific rotation: [α]D +116° or +104° (c = 0.5, alcohol)
• Polar Surface Area (PSA): 44.7
• XLogP3: 2.1

Origin

Quinamine was first isolated by Hesse from the bark of Cinchona succirubra, and was subsequently found in the bark of a number of species of the genus, especially Cinchona ledgeriana—hence the catalog name “alkaloid B from Cinchona ledgeriana.” It is also found as a natural compound in Cinchona calisaya, Cinchona pubescens and species of the genus Remijia. In all cases it is a minor alkaloid accompanying the main quinine bases.

Chemical features

The difference from other alkaloids of cinchona is manifested in oxidation reactions: quinamine does not produce a quinoline derivative, instead vinyl quinuclidine carboxylic acid is formed. The reason is in the structure - the indole part of the molecule is closed in the furan ring through the tertiary hydroxyl at C-3a, and the quinuclidine fragment with the vinyl group is attached to the same node atom. The substance is optically active; two specific rotation values ​​are given for it - +116° and +104° at a concentration of 0.5 in alcohol.

Scope of application

• reference sample for HPLC and LC-MS profiling of cinchona bark alkaloids
• control of the composition of raw materials and preparations based on cinchona
• comparative sample in the isolation and structural identification of minor alkaloids Cinchona and Remijia
• parent compound for laboratory studies of indole alkaloids

Handling and storage

The vapor pressure at 25 °C is zero - the substance is not volatile, and for this reason there are no losses when stored in open containers. The GHS classification is not shown in the supplier card. The product is for research purposes and is not intended for medical or food use. Keep the container closed and protected from light, work with gloves and safety glasses, handle as a substance with an unknown toxicity profile.