Basic information
- CAS
69-05-6- Standard SMILES
CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)cc12.Cl.Cl- InChIKey
UDKVBVICMUEIKS-UHFFFAOYSA-N- Molecular formula
- C23H32Cl3N3O
- Average molar mass
- 472.9 g/mol
- Monoisotopic mass
- 471.161096
Overview
Quinacrine dihydrochloride appears as bright yellowish needles or bright yellow powder. Odorless. pH of a 1% aqueous solution is about 4.5.(NTP, 1992). Used as an anti-malarial drug. Moderately toxic.
Names & identifiers
- Preferred name
- Quinacrine Dihydrochloride
- IUPAC
- 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride
- English name
- Quinacrine dihydrochloride
- Molecular formula
- C23H32Cl3N3O
- Molecular weight
- 472.88
Names & synonyms
QUINACRINE DIHYDROCHLORIDE69-05-6Mepacrine dihydrochlorideCrinodoraItalchinMetochinMetoquinMetoquinePalacrinPalusanPentilenChemiochin
Show more names
QUINACRINEMEPACRINEATABRINEsn390erion866r.p.erionHCl
MalaricidaMethoquineMecrylChinacrin hydrochloride866 R.P.chinacrin2-Chloro-5-(omega-diethylamino-alpha-methylbutylamino)-7-methoxyacridine dihydrochlorideAcridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-, dihydrochloride
Database identifiers
- CAS
69-05-6- PubChem CID
- 6239
- DTXSID
DTXSID6025985- ChEMBL
CHEMBL2105615、CHEMBL554190- UNII
- 81A613ZZ6X
- EC Number
- 200-700-8
Properties
Computed structural properties
- Topological polar surface area
- 37.4 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 461
Experimental & physicochemical properties
Solubility10 to 50 mg/mL at 64 °F (NTP, 1992)
Melting Point478 to 482 °F (Decomposes) (NTP, 1992)
Physical DescriptionQuinacrine dihydrochloride appears as bright yellowish needles or bright yellow powder. Odorless. pH of a 1% aqueous solution is about 4.5.(NTP, 1992). Used as an anti-malarial drug. Moderately toxic.
Collision Cross Section195.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 249 · 249-251℃ (Decomposition)
- Density
- 1.2962 · 1.2962 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- 15 C · +15C to +30C
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
- pka
- -6.3 · pKa -6.3(H2O t undefined I not reported but low) (Uncertain)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine dihydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, dihydrochloride: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include discoloration of the skin, sclera and urine, exfoliative dermatitis, acute hepatic necrosis, agranulocytosis, aplastic anemia, corneal edema and psychosis.
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity ProfileQUINACRINE DIHYDROCHLORIDE is an acidic salt of an amine. React as a weak acid to neutralize bases.
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used to treat tapeworm infestations in man or animals.
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
UsesA non-specific PLA2 inhibitor. and acetylcholine receptor antagonist
UsesQuinacrine is a derivative of acridine that is chemically and clinically very similar to 4-aminoquinolines. It was the primary drug for prevention and therapy of malaria during World War II. Today it is rarely used for treating malaria, although it is used to treat amebiasis. Synonyms of this drug are mepacrine, atabrine, acrisuxin, and others. In treating resistant forms of malaria, tetracycline is also used in combination with pyrimethamine, sulfonamides, sulfones, and dapsone, which is widely used for treating leprosy (as a rule, in combination with pyrimethamine).
UsesQuinacrine dihydrochloride has been used:in its uptake and accumulation studies in mouse lung slices using fluorescence microscopein the staining of ATP vesicles in mesenchymal stem cells (MSCs)in uptake-release assay for characterization of dense granule functionality of platelets
General DescriptionBright yellowish needles or bright yellow powder. Odorless. pH of a 1% aqueous solution is about 4.5.. Used as an anti-malarial drug. Moderately toxic.
Suppliers93 total
上海康恩博医药科技有限公司17510465506 · [email protected]
Related reactions
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Compound notes
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