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Aminacrine Hydrochloride
Also known as: Acridin-9-amine hydrochloride, 134-50-9, Aminacrine hydrochloride, Aminacrine hcl, Acramine yellow, Aminoacridine hydrochloride
Molecular Formula
C13H11ClN2
Molecular Weight
230.69  g/mol
InChI Key
FTGPOQQGJVJDCT-UHFFFAOYSA-N
FDA UNII
OR5RM3Q5QL

A highly fluorescent anti-infective dye used clinically as a topical antiseptic and experimentally as a mutagen, due to its interaction with DNA. It is also used as an intracellular pH indicator.
1 2D Structure

Aminacrine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
acridin-9-amine;hydrochloride
2.1.2 InChI
InChI=1S/C13H10N2.ClH/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13;/h1-8H,(H2,14,15);1H
2.1.3 InChI Key
FTGPOQQGJVJDCT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)N.Cl
2.2 Other Identifiers
2.2.1 UNII
OR5RM3Q5QL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9 Aminoacridine

2. 9-aminoacridine

3. Acridinamine

4. Aminacrine

5. Aminacrine Hydrochloride

6. Aminoacridine

7. Aminoacridine Hydrochloride

8. Aminopt

9. Hydrochloride, Aminacrine

10. Hydrochloride, Aminoacridine

11. Mykocert

2.3.2 Depositor-Supplied Synonyms

1. Acridin-9-amine Hydrochloride

2. 134-50-9

3. Aminacrine Hydrochloride

4. Aminacrine Hcl

5. Acramine Yellow

6. Aminoacridine Hydrochloride

7. Monacrin

8. Mycosert

9. 9-aminoacridinium Chloride

10. Nsc-7571

11. 9-acridinamine Monohydrochloride

12. Monacrin Hydrochloride

13. 9-acridinamine, Monohydrochloride

14. 9-aminoacridine Monohydrochloride

15. 5-aminoacridine Hydrochloride

16. Aminacrine Hydrochloride [usan]

17. Aminoacridine Hcl

18. Or5rm3q5ql

19. Chebi:74837

20. Nsc7571

21. Nsc 7571

22. Aminoakridin

23. Quench

24. Aminacrine Hydrochloride (usan)

25. Caswell No. 033a

26. Ccris 3802

27. Hsdb 4505

28. Acridine, 9-amino-, Hydrochloride

29. Einecs 205-145-5

30. Unii-or5rm3q5ql

31. 9-aminoacridine Hcl

32. Acridine, 9-amino-, Monohydrochloride

33. Epa Pesticide Chemical Code 055503

34. Acridin-9-ylamine Hydrochloride Monohydrate

35. Ai3-16947

36. Monacrin (tn)

37. 9-acridinamine Hcl

38. Acridin-9-aminehydrochloride

39. Acridin-9-amine;hydrochloride

40. Schembl635597

41. Chembl1330022

42. Dtxsid8030473

43. 9-aminoacridinehydrochloride

44. 9-acridinamine Hydrochloride Hydrate

45. Aminacrine Hydrochloride [mi]

46. Mfcd00012663

47. 9-acridinamine, Hydrochloride (1:1)

48. Akos015903444

49. Wln: T C666 Bnj Iz & Gh

50. Aminacrine Hydrochloride [hsdb]

51. Aminacrine Hydrochloride [vandf]

52. Aminoacridine Hydrochloride [mart.]

53. Aminoacridine Hydrochloride [who-dd]

54. Db-042240

55. A0619

56. Ft-0621613

57. D02905

58. W-105829

59. Q27144949

60. Z57039678

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 230.69 g/mol
Molecular Formula C13H11ClN2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass230.0610761 g/mol
Monoisotopic Mass230.0610761 g/mol
Topological Polar Surface Area38.9 Ų
Heavy Atom Count16
Formal Charge0
Complexity207
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Anti-Infective Agents, Local; Fluorescent Dyes; Indicators and Reagents; Mutagens

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


AMINACRINE HYDROCHLORIDE EXERTS GERMICICAL ACTIONS AGAINST BOTH GRAM-POSITIVE & GRAM NEGATIVE BACTERIA & AGAINST FUNGI & TRICHOMONADS. IT IS NOT INACTIVATED BY PUS, SECRETIONS, OR BODY FLUIDS. IN THE TREATMENT OF VAGINAL CANDIDIASIS, TRICHOMONIASIS, OR HAEMOPHILUS INFECTIONS ...

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 980


ITS PRINCIPAL USE IS IN THE TREATMENT OF INFECTIONS OF VAGINA & EXOCERVIX, SUCH AS MONILIASIS, TRICHOMONAL VAGINITIS...OR AS PROPHYLACTIC AGENT IN VARIOUS GYNECOLOGICAL PROCEDURES. IN ADDITION, IT FINDS USE IN TREATMENT OF TINEA VERSICOLOR. IT HAS ALSO BEEN USED IN TREATMENT OF MASTITIS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1102


EXPTL USE: EVIDENCE IS PRESENTED TO SUPPORT USE AS A SAFE & EFFECTIVE SURGICAL IRRIGANT IN DENTISTRY. AVAIL LITERATURE CONFIRMS THAT IT IS A POTENT ANTIMICROBIAL AGENT, EFFECTIVE AGAINST WIDE RANGE OF MICROORGANISMS COMMONLY FOUND IN SEPTIC WOUNDS & CAUSING MINIMAL TISSUE IRRITATION. ITS USE FOR ROUTINE ROOT CANAL IRRIGATION & AS ANTISEPTIC IN MANAGEMENT OF MAXILLOFACIA ABSCESSES IS RECOMMENDED.

SCHMITZ JP; 9-AMINOACRIDINE--ITS PRESENT STATUS AND CURRENT RECOMMENDATIONS FOR USE AS A SURGICAL AND ENDODONTIC IRRIGANT IN DENTISTRY; ORAL SURG 50(3) 273 (1980)


MEDICATION (VET): Antiseptic

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 72


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


Fluorescent Dyes

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)


Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)


Mutagens

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)


5.2 Mechanism of Action

IN PRESENCE OF 9-AMINOACRIDINE-HCL, BACTERIOPHAGE P22 OF SALMONELLA TYPHIMURIUM WAS KILLED ON IRRADIATION WITH VISIBLE LIGHT; NEITHER THE COMPD NOR THE LIGHT ALONE INACTIVATED THE PHAGE. THE ACRIDINE INDUCED DAMAGE IN THE PHAGES BY 4 INDEPENDENT MODES: 1) FROM SHIFT MUTAGENESIS DURING PHAGE DNA REPLICATION; 2) ACRIDINE-SENSITIZED PHYTOTOXICITY TO PHAGE PARTICLES; 3) ACRIDINE-SENSITIZED PHOTOMUTAGENESIS; AND 4) INTERFERENCE WITH VIRUS ASSEMBLY. KINETIC ANALYSIS OF FORMATION & PHOTOINACTIVATION OF COMPLEX BETWEEN 9-AMINOACRIDINE-HCL & P22 INDICATED THAT ACRIDINES BOUND TO DNA BACKBONE & INTERCALATED BETWEEN THE BASIS COULD MEDIATE LETHAL DAMAGE TO DNA-INJECTION PROTEINS.

LOECHLER E ET AL; THE USE OF SALMONELLA BACTERIOPHAGE P22 TO STUDY THE MULTIPLE MECHANISMS OF ACRIDINE-INDUCED DAMAGE; NATO CONF SER 1, 5A(IN VITRO TOXIC TEST ENVIRON AGENTS: CURR FUTURE POSSIBILITIES, PT A) 79 (1983)


INFLUENCE OF SELF-COMPLEMENTARY OLIGODEOXYNUCLEOTIDES ON CHEMICAL SHIFTS OF PROTONS OF MUTAGENIC 9-AMINOACRIDINE WAS MEASURED. UPFIELD SHIFTS INDICATIVE OF INTERCALATIVE BINDING ARE FOUND IN CASES OF DG-DC, DC-DG & DA-DT-DG-DC-DA-DT BUT NOT IN DA-DT. GEOMETRIES FOR COMPLEXES ARE COMPATIBLE WITH CHEMICAL-SHIFT DATA & X-RAY STRUCTURE OF COMPLEX BETWEEN RI5C-RG & 9-AMINOACRIDINE DETERMINED BY SAKORE ET AL CAN BE IDENTIFIED USING RECENT THEORETICAL ESTIMATES OF SHIFTS INDUCED BY NUCLEOTIDE BASES.

REUBEN J ET AL; STRUCTURE OF MUTAGEN NUCLEIC ACID COMPLEXES IN SOLUTION: PROTON CHEMICAL SHIFTS IN 9-AMINOACRIDINE COMPLEXES WITH DG-DC, DC-DG, & DA-DT-DG-DC-DA-DT; BIOCHEMISTRY 17(14) 2915 (1978)


INTERACTIONS OF 9-AMINOACRIDINE-HCL WITH IONIC CHANNELS WERE STUDIED IN INTERNALLY PERFUSED SQUID AXONS. KINETICS OF BLOCK OF SODIUM CHANNELS WITH 9-AMINOACRIDINE-HCL VARIED DEPENDING ON VOLTAGE-CLAMP PULSES & THE STATE OF GATING MACHINERY OFF SODIUM CHANNELS. IN AN AXON WITH INTACT H GATE, THE BLOCK EXHIBITED FREQUENCY- & VOLTAGE-DEPENDENT CHARACTERISTICS. IT ALSO BLOCKED POTASSIUM CHANNELS.

YEH JZ; DYNAMICS OF 9-AMINOACRIDINE BLOCK OF SODIUM CHANNELS IN SQUID AXONS; J GEN PHYSIOL 73(1) 1 (1979)


EFFECT OF SEQUENCE ON BINDING TO DNA WAS INVESTIGATED BY STUDYING ITS INTERACTION WITH DEOXYDINUCLEOSIDE PHOSPHATES OF DIFFERENT SEQUENCES USING PNMR. SIMPLEST MODEL THAT FITS THE DATA INCL 1) DIMERIZATION OF 9-AMINOACRIDINE AND 2) A MIXTURE OF 1:1 & 2:1 (DINUCLEOSIDE PHOSPHATE/9-AMINOACRIDINE) COMPLEXES. THE 1:1 COMPLEXES SEEM TO INVOLVE INTERACTION OF THE RING NITROGEN WITH THE BACKBONE PHOSPHATE & STACKING OF ONE OR BOTH CHROMOPHORES ON THE ACRIDINE; PREFERENCE IN BINDING WAS OBSERVED FOR ALTERNATING (PURINE-PYRIMIDINE OR PYRIMIDINE-PURINE) OVER NON-ALTERNATING (PURINE-PURINE) DINUCLEOSIDE PHOSPHATES. THE 2:1 COMPLEXES INVOLVE INTERCALATION OF ACRIDINE BETWEEN 2 COMPLEMENTARY DINUCLEOSIDE PHOSPHATE STRANDS WITH WEAK SEQUENCE PREFERENCES IN BINDING. STEREOCHEMISTRY OF INTERACTION DIFFERS BETWEEN NON-ALTERNATING PURINE-PURINE SEQUENCES & ALTERNATING PYRIMIDINE-PURINE OR PURINE-PYRIMIDINE SEQUENCES IN HAVING 9-AMINOACRIDINE STACKED WITH PURINES OF 1 STRAND RATHER THAN STRADDLING PURINES ON OPPOSITE STRANDS. DIFFERENCES IN STEREOCHEMISTRY COULD POSSIBLY BE DETERMINING FACTOR IN FRAMESHIFT SEQUENCE SPECIFICITY.

YOUNG PR, KALLENBACH NR; BINDING OF 9-AMINOACRIDINE TO DEOXYDINUCLEOSIDE PHOSPHATES OF DEFINED SEQUENCE: PREFERENCES AND STEREOCHEMISTRY; J MOL BIOL 145(4) 785 (1981)


For more Mechanism of Action (Complete) data for 9-AMINOACRIDINE HYDROCHLORIDE (6 total), please visit the HSDB record page.


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