Primaquine

Base Information

• Chemical Name: Primaquine
• CAS No.: 90-34-6
• Molecular Formula: C15H21 N3 O
• Molecular Weight: 259.351
• Hs Code.: 2933499090
• European Community (EC) Number: 201-987-2
• NSC Number: 27296
• UNII: MVR3634GX1
• DSSTox Substance ID: DTXSID8023509
• Nikkaji Number: J4.316H
• Wikipedia: Primaquine
• Wikidata: Q419834
• NCI Thesaurus Code: C62071
• RXCUI: 8687
• Pharos Ligand ID: W224JDGJAAP5
• Metabolomics Workbench ID: 43319
• ChEMBL ID: CHEMBL506
• Mol file: 90-34-6.mol

Synonyms:Diphosphate, Primaquine;Phosphate, Primaquine;Primacin;Primaquine;Primaquine Diphosphate;Primaquine Phosphate

Chemical Property of Primaquine

Chemical Property:

• Melting Point: 25°C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: bp0.2 175-179°
• PKA: pKa 3.74/9.99(H2O,t =25) (Uncertain)
• PSA: 60.17000
• Density: 1.0313 (rough estimate)
• LogP: 3.55600
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 718.4g/L(25 oC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 259.168462302
• Heavy Atom Count: 19
• Complexity: 262

Purity/Quality:

98%,99%, ^*data from raw suppliers

Primaquine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antimalarial Agents
• Canonical SMILES: CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
• Recent ClinicalTrials: Momordica Charantia and Dihydroartemisinin-piperaquined-primaquine for Uncomplicated Plasmodium Falciparum Malaria Patients in Southwest Sumba Regency
• Indications: Primaquine is used for the radical treatment of P. vivax and P. ovale infections. It has also been used in large populations to avoid spread of chloroquine-resistant strains of falciparum malaria (through its gametocytocidal action). Primaquine is the least toxic and most effective of the 8- aminoquinoline antimalarial compounds. The mechanism by which 8-aminoquinolines exert their antimalarial effects is thought to be through a quinoline–quinone metabolite that inhibits the coenzyme Q–mediated respiratory chain of the exoerythrocytic parasite.
• Uses: Antimalarial . Primaquine is the most effective and most toxic drug from the whole series of known 8-aminoquinolines. It is generally used for treating exoerythrocyte forms of malaria caused by P. vivax and P. ovale. It also acts on the sexual forms of the plasmodia, which die in the human body upon using this drug. Primaquine is used for treating and preventing late relapses of 3- and 4-day malaria as well as tropic malaria. Synonyms of this drug are avlon and others. Primaquine is an intermediate in the synthesis of Primaquine-d3 Diphosphate (P733502). Primaquine-d3 Diphosphate is an isotope labelled Primaquine (P733500), which is an antimalarial.
• Clinical Use: Primaquine is the only 8-aminoquinolinecurrently in use for the treatment of malaria. It is not usedfor prophylaxis. Its spectrum of activity is one of the narrowestof the currently used antimalarial drugs being indicatedonly for exoerythrocytic P. vivax malaria. To treat endoerythrocytic P. vivax, chloroquineor a drug indicated for chloroquine-resistant P. vivax isused with primaquine. In addition to its approved indication,it is also active against the exoerythrocytic stages ofP. ovale and primary exoerythrocytic stages of P. falciparum.Primaquine also inhibits the gameocyte stage that eliminates the form required to infect themosquito carrier. In vitro and in vivo studies indicate thatthe stereochemistry at the asymmetric is not important forantimalarial activity. There appears to be less toxicity withthe levorotatory isomer, but this is dose dependent andmay not be that important at the doses used to treatexoerythrocytic P. vivax malaria.Although structurally related to the cinchona alkaloids,the 8-aminoquinolines act by a different mechanism of action.Primaquine appears to disrupt the parasite’s mitochondria.The result is disruption of several processes includingmaturation into the subsequent forms. An advantage is destroyingexoerythrocytic forms before the parasite can infecterythrocytes. It is the latter step in the infectious process thatmakes malaria so debilitating. Radical cure of malaria caused by P. vivax or P. ovale Mild or moderately severe infections with Pn. jirovecii (in combination with clindamycin). Because of its gametocytocidal properties, primaquine has been used rarely in a single dose to prevent the spread of chloroquine- resistant P. falciparum. Primaquine is an important antimalarial because it is essentially the only drug effective against the liver (exoerythrocytic) forms of the malarial parasite. The drug also kills the gametocytes in all four species of human malaria. Primaquine is relatively ineffective against the asexual erythrocyte forms. Primaquine finds its greatest use in providing a radical cure for P. vivax and P. ovale malaria.

Technology Process of Primaquine

There total 24 articles about Primaquine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

primaquine diphosphate (63-45-6) → Primaquine (90-34-6,57152-58-6)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 2h; pH=10; Darkness;

DOI:10.1016/j.bmcl.2016.03.027

Reference yield:

methyl α-D-galactopyranoside (3396-99-4) → Primaquine (90-34-6,57152-58-6)

Guidance literature:

With hydrogenchloride; In methanol;

Reference yield:

8-(4-ethoxycarbonylamino-1-methylbutylamino)-6-methoxyquinoline (1185934-52-4) → Primaquine (90-34-6,57152-58-6)

Guidance literature:

With sodium hydroxide; In water; acetonitrile; at 37 ℃; Kinetics; aq. borate buffer;

DOI:10.1016/j.bmc.2011.11.059

upstream raw materials:

Leu-Ala-Leu-primaquine

Ala-Leu-Ala-Leu-primaquine

Ala-Leu-Ala-Lys-primaquine

6-methoxyquinolin-8-amine

Downstream raw materials:

N-p-nitrobenzoyl primaquine

primaquine diphosphate

Refernces

• 1、 Beus, Maja,Perkovi?, Ivana,Persoons, Leentje,Schols, Dominique,Zorc, Branka. "Itaconic acid hybrids as potential anticancer agents". . . Retrieved 2020/10/15.
• 2、 Carvalho, Rita C.C.,Martins, Wagner A.,Silva, Tayara P.,Kaiser, Carlos R.,Bastos, Mo?nica M.,Pinheiro, Luiz C.S.,Krettli, Antoniana U.,Boechat, Núbia. "New pentasubstituted pyrrole hybrid atorvastatin-quinoline derivatives with antiplasmodial activity". supporting information. p. 1881 - 1884. Retrieved 2016/04/05.