quinacrine

Also known as GNF-Pf-5448, Mepacrine, 6-chloro-9-((4-(Diethylamino)-1-methylbutyl)amino)-2-methoxyacridine, 3-chloro-7-Methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine, N(4)-(6-chloro-2-Methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine, 2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine, 3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine

Mepacrine, also called quinacrine or by the trade names Atabrine or Atebrin, is a medication with several uses. It is related to chloroquine and mefloquine. Although available from compounding pharmacies, as of August 2020 approved formulations are not available in the United States.

Chemical data

Formula: C23H30ClN3O
Molecular weight: 400 g/mol
IUPAC name: 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
SMILES: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC
InChIKey: GPKJTRJOBQGKQK-UHFFFAOYSA-N
XLogP: 6
Polar surface area: 37.4 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

5,305 papers

Quinacrine revised.Human reproduction update · 1995
Quinacrine sterilization (QS): time for reconsideration.Contraception · 2015
Quinacrine Treatment of Nitroimidazole-Refractory Giardiasis.The Journal of infectious diseases · 2022
Quinacrine-resistant Giardia duodenalis.Parasitology · 1996
Quinacrine: sclerosing agent of the utero-tubal junction in women, with anticarcinogenic actions in transplanted tumors in mice.International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics · 1995

via PubMed

Wikidata facts

Mass: 399.208

Show 4 more facts

chemical formula: C₂₃H₃₀ClN₃O
canonical SMILES: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC
defined daily dose: 0.3
Commons category: Quinacrine

Sources (5)

via Wikidata · CC0

~6 min read

Article

11 sections

Contents

Medical uses
Mechanism
History
Antiprotozoal
Anthelmintics
Creutzfeldt–Jakob disease
Non-surgical sterilization for women
Skin dye
See also
References
External links

==Medical uses== thumb|left|''These men didn't take their Atabrine''; this sign was posted at the 363rd Station Hospital on Papua New Guinea during World War II The main uses of mepacrine are as an antiprotozoal, antirheumatic, and an intrapleural sclerosing agent.