(±)-Quinacrine
Also known as quinacrine, mepacrine, atabrine
Key facts
What buyers check first
- Appearance
- Bright yellow crystals
- Melting point
- 248 °C
- Solubility
- 1g in 36 ml water
- HS code
- 293399
- Category
- Screening compounds

What is (±)-Quinacrine?
Plain description, key identifiers and synonyms
Quinacrine is a member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9. It has a role as an antimalarial and an EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor. It is a member of acridines, an aromatic ether, an organochlorine compound and a tertiary amino compound. It derives from a hydride of an acridine.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
- CAS number
- 83-89-6 CAS number cross-checked
- EC number
- 201-508-7
- Molecular formula
- C23H30ClN3O
- UNII
- H0C805XYDE
- MDL number
- MFCD00242796
- InChIKey
- GPKJTRJOBQGKQK-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
- SMILES (canonical and isomeric)
- CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC
Synonyms
- quinacrine
- mepacrine
- atabrine
- Acrinamine
- Acriquine
- Antimalarina
- Akrichin
- Haffkinine
- Erion
- Italchine
- Quinactine
- Mepacrina
- Mepacrinum
- 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine
- 2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine
- 3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine
- atebrin
- 1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-
- Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-
- 6-Chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine
- 6-chloro-N-(5-(diethylamino)pentan-2-yl)-2-methoxyacridin-9-amine
- N'-(6-chloro-2-methoxyacridin-9-yl)-N,N-diethylpentane-1,4-diamine
- Acridine, 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxy-
- (+-)-Quinacrine
- Dimesylate, Quinacrine
Show all 38 synonymsShow fewer synonyms
- Monoacetate, Quinacrine
- Monomesylate, Quinacrine
- Hydrochloride, Quinacrine
- Monohydrochloride, Quinacrine
- acrichinum (for the hydrochloride)
- acrichine
- Quinacrine, Mepacrine
- Quinacrine hydrochloride
- St 439
- (+/-)-Quinacrine
- 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
- Mepacrine hydrochloride
- Quinacrine (hydrochloride,hydrate)
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
| Appearance | Bright yellow crystalsexp.Measured value |
|---|---|
| Melting point | 248 °Cexp.Measured value |
| Solubility | 1g in 36 ml waterexp.Measured value |
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 399.97 g/molcalc.Computed value |
|---|---|
| Exact mass | 399.2077 Dacalc.Computed value |
| LogP (octanol/water) | 5.97calc.Computed value |
| Topological polar surface area | 37.39 Ųcalc.Computed value |
| Hydrogen bond donors | 1calc.Computed value |
| Hydrogen bond acceptors | 4calc.Computed value |
| Rotatable bonds | 9calc.Computed value |
| Heavy atoms | 28calc.Computed value |
| Rings | 3calc.Computed value |
| Aromatic rings | 3calc.Computed value |
| Fraction sp3 carbons | 0.44calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 1calc.Computed value |
| Lipinski rule of five | Passes (1 violation)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
c1ccc2nc3ccccc3cc2c1
3 rings, 14 atoms, the Acridine ring system.
1,068 other chemicals share this scaffoldSafety and hazards
GHS classification summary, not a safety data sheet
No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
(±)-Quinacrine suppliers
Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings
- Spain, BarcelonaUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- United States, HaywardUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- United States, SomervilleUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- Price on request
- United States, HauppaugeUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- United States, San DiegoUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- Hong Kong, Hong KongUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- China, WuhanUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- United Kingdom, HadfieldUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
- China, HangzhouUnclaimed profile(±)-QuinacrineGrade, purity and minimum order on requestPrice on request
Suppliers marked Unclaimed profile have not claimed their profile yet. They are not verified by CompoundList, their offers are price on request and details may have changed, so please confirm them with the supplier. Company representatives can claim a profile with a business email on the company's own website domain. Our team verifies each claim and sends the result by email.
Where suppliers are based
17 suppliers in 7 countries
- United States6
- China5
- Hong Kong2
- Spain1
- France1
- United Kingdom1
- and 1 more countries
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(±)-Quinacrine price
Indicative price range per kg from live supplier offers
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Uses and applications
What the substance is used for, by industry and function
Antimalarial, anthelmintic, antiprotozoal (vet).
Veterinary medication:.
Industries and functions
Pharmacological actions
- Anticestodal Agents
- Antimalarials
- Antinematodal Agents
- Antineoplastic Agents
- Enzyme Inhibitors
Roles
- antiamoebic agent
- antiinfective agent
- antimalarial
- antimicrobial agent
- antimicrobial drug
- antineoplastic agent
- antiparasitic agent
- antiplasmodial drug
- antiprotozoal drug
- enzyme inhibitor
- pharmaceutical
Pharmacology
Quinacrine Hydrochloride is the dihydrochloride salt of the 9-aminoacridine derivative quinacrine with potential antineoplastic and antiparasitic activities. Quinacrine may inhibit the transcription and activity of both basal and inducible nuclear factor-kappaB (NF-kappaB), which may result in the induction of tumor suppressor p53 transcription, the restoration of p53-dependent apoptotic pathways, and tumor cell apoptosis. Continuous NF-kappaB signaling, present in many tumors and in chronic inflammatory processes, promotes the expression of antiapoptotic proteins and cytokines while downregulating the expression of proapoptotic proteins, such as p53.
How it is made
Prepared by condensing 1-diethylamino-4-aminopentane with 3,9-dichloro-7-methoxyacridine: F. Mietzsch, H. Mauss, German patents 553,072, 571,499 (1934), (corresponds to) US 2,113,357 (1938 to Winthrop Chemical) ... Jensch, Eisleb, US 1,782,727 (1930), Schulemann et al., US 1,889,704 (1932).
Prepared by treating quinacrine base with methanesulfonic acid in alcoholic solution and precipitation methanesulfonate with ether. (Methanesulfonate)
2,4-Dichlorobenzoyl chloride + p-anisidine + 4-amino-1-diethylaminopentane (Friedel-Crafts acylation/amine formation/reductive amination)
Regulatory status
Inventories, regulations and trade controls that list this substance
No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code (±)-Quinacrine is traded under.
Heterocyclic compounds with nitrogen hetero-atom(s) only, other
- Slovenia31.7%
- Italy24.2%
- United States5.0%
* Partner reported figures, a lower bound.
The HS code shown for (±)-Quinacrine is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about (±)-Quinacrine, based on the data on this page
What is (±)-Quinacrine?
What is the CAS number of (±)-Quinacrine?
What is the molecular formula and weight of (±)-Quinacrine?
What is (±)-Quinacrine used for?
Is (±)-Quinacrine hazardous?
What is the HS code of (±)-Quinacrine?
Where can I buy (±)-Quinacrine?
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Guides for buyers
Practical guides that help when you source, ship or handle (±)-Quinacrine
- Guide, Chemical identityCAS registry numbers explainedWhat a CAS number identifies, how the check digit works, why one chemical can have several numbers and what a CAS number cannot tell you about a product.Read
- Article, SourcingHow to write an RFQ that gets fast and accurate quotesWhat suppliers need to quote quickly and comparably: exact product identity, quantity and packing, delivery terms, documents, samples and payment, with a ready to use template.Read
- Guide, Trade and logisticsHS codes for chemicals and why they matterHow the Harmonized System classifies chemicals, the chapters that matter, the rules for chemically defined compounds and mixtures, and practical steps to find the right code.Read
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