molecular formula C14H21N3O3 B1677833 Oxamniquine CAS No. 21738-42-1

Oxamniquine

Cat. No.: B1677833
CAS No.: 21738-42-1
M. Wt: 279.33 g/mol
InChI Key: XCGYUJZMCCFSRP-UHFFFAOYSA-N
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Preparation Methods

Synthetic Routes and Reaction Conditions: The synthesis of oxamniquine begins with a molecule containing a quinoline structure. The process involves several key reactions, including substitution and reduction . Initially, the starting molecule undergoes a substitution reaction activated by sodium carbonate to form an intermediate structure. This intermediate then undergoes a bimolecular nucleophilic substitution (SN2) reaction, followed by hydrogenation with nickel as a catalyst . The final steps involve nitration using concentrated nitric and sulfuric acids, followed by microbial oxidation to yield this compound .

Industrial Production Methods: Industrial production of this compound follows similar synthetic routes but on a larger scale. The process is optimized for yield and purity, ensuring that the final product meets pharmaceutical standards. The use of automated reactors and stringent quality control measures are integral to the industrial synthesis of this compound .

Chemical Reactions Analysis

Properties

IUPAC Name

[7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
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InChI

InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

XCGYUJZMCCFSRP-UHFFFAOYSA-N
Source PubChem
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Description Data deposited in or computed by PubChem

Canonical SMILES

CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
Source PubChem
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Description Data deposited in or computed by PubChem

Molecular Formula

C14H21N3O3
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DSSTOX Substance ID

DTXSID3023398
Record name Oxamniquine
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Molecular Weight

279.33 g/mol
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Physical Description

Solid
Record name Oxamniquine
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Solubility

1 part in about 3300 parts of water at 27 °C, 1.24e-01 g/L
Record name Oxamniquine
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Mechanism of Action

Oxamniquine may associate with an irreversible inhibition of the nucleic acid metabolism of the parasites. A hypothesis has been put forth that the drug is activated by a single step, in which a schistosome sulfotransferase enzyme converts oxamniquine into an ester (probably acetate, phosphate, or sulfate). Subsequently, the ester spontaneously dissociates, the resulting electrophilic reactant is capable of alkylation of schistosome DNA., Causes the worms to be dislodged from their usual site of residence in the mesenteric veins to the liver where they are retained and subsequently killed by host tissue reactions (eg, phagocytosis). The dislodgment of worms appears to result principally from contraction and paralysis of their musculature and subsequent immobilization of their suckers, which causes the worms to detach from the blood vessel wall, thereby allowing passive dislodgement by normal blood flow., Hycanthone-sensitive and hycanthone-resistant schistosomes (which are also sensitive and resistant to oxamniquine) were exposed in vitro to tritium-labelled oxamniquine. The initial uptake of the drug into the schistosomes was essentially the same for the 2 strains. The homogenate of worms incubated with tritiated oxamniquine was fractionated and a purified DNA fraction was obtained by ethanol precipitation, RNAase and protease digestion, repeated phenolchloroform extractions, cesium chloride gradient centrifugation and extensive dialysis. The DNA fraction from sensitive worms contained radioactive oxamniquine at a level corresponding to about 1 drug molecule per 50,000 base pairs, while the DNA from resistant worms contained essentially no drug. The results support the hypothesis that oxamniquine, like hycanthone, exerts its activity by alkylating macromolecules of sensitive schistosomes.
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Color/Form

Pale yellow crystals from isopropanol, Yellow-orange, crystalline solid

CAS No.

21738-42-1, 40247-39-0, 119678-90-9
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Melting Point

147-149 °C, 147 - 149 °C
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Record name Oxamniquine
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Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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