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Pyronine

HCID 7085
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
92-32-0
Standard SMILES
CN(C)c1ccc2cc3ccc(=[N+](C)C)cc-3oc2c1.[Cl-]
InChIKey
INCIMLINXXICKS-UHFFFAOYSA-M
Molecular formula
C17H19N2O.Cl
Average molar mass
302.8 g/mol
Monoisotopic mass
302.1185909

Overview

Pyronin Y is an organic chloride salt having 6-(dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium as the cation. Used with methyl green to selectively demonstrate RNA (red) in contrast to DNA (green) with the Unna-Pappenheim method. It has a role as a histological dye. It is an iminium salt and an organic chloride salt. It contains a pyronin Y cation.

Names & identifiers

Preferred name
Pyronine
IUPAC
[6-(dimethylamino)xanthen-3-ylidene]-dimethylazanium chloride
English name
PYRONIN Y
Molecular formula
C17H19ClN2O
Molecular weight
302.8

Names & synonyms

Pyronin Y92-32-0Pyronine YPyroninePyronin GPyronin YellowPyronine GTetramethyl pyronin3,6-Bis(dimethylamino)xanthylium chlorideMethyl pyroninXanthylium, 3,6-bis(dimethylamino)-, chloridePyronine ZH
Show more names
Pyonin GPyonin YCI 45005PYRONIN J
C.I. 45005tetramethyldiaminoxanthylium chlorideSchultz No. 853NSC-10454W659G165T1CHEBI:8682DTXSID8059051CI-45005

Database identifiers

CAS
92-32-0
PubChem CID
7085
DTXSID
DTXSID8059051
ChEMBL
CHEMBL1486690
ChEBI
CHEBI:8682
UNII
W659G165T1
EC Number
202-147-8

Properties

Computed structural properties

Topological polar surface area
15.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
21
Formal charge
0
Complexity
480

Experimental & physicochemical properties

Chemical ClassesDyes -> Acridine Dyes
Physical Description · 2 items

Liquid

Lustrous green solid; [Merck Index] Iridescent green crystals; [Amresco MSDS]

Physicochemical properties

Melting point
250 · 250-260 °C(lit.)
storage temp.
room temp
solubility
Soluble in water; sparingly soluble in ethanol, ethylene glycol, methyl cellosolve
form
Powder/Solid
Colour Index
45005 · 45005
color
Pink
Water Solubility
Soluble in water. Also soluble in methyl cellosolve (9 mg/mL) and ethanol (3 mg/mL).
λmax
548 nm · 548 nm
Merck
13 · 13,8097
BRN
3795789 · 3795789
Stability
Stable. Incompatible with strong oxidizing agents.

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 · 4 items

Warning

H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: Methanaminium, N-[6-(dimethylamino)-3H-xanthen-3-ylidene]-N-methyl-, chloride

Xanthylium, 3,6-bis(dimethylamino)-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Xanthylium, 3,6-bis(dimethylamino)-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Xanthylium, 3,6-bis(dimethylamino)-, chloride: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses changes in kidneys (acute tubular necrosis) in intravenous lethal-dose studies of mice (LD50 = 179 mg/kg); [RTECS] A skin and strong eye irritant; Targets the kidney and bladder; [Amresco MSDS]
Hazard Classes and CategoriesMuta. 2 (100%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
BQ1450000
hs_code
32041300
risk_code
68-36/37/38

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.

Uses & manufacturing

UsesUsed as a bacterial and biological stain; [Merck Index]
U.S. Production2022: 11,116 lb
Industry UsesFiller
General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

Xanthylium, 3,6-bis(dimethylamino)-, chloride (1:1): ACTIVE

Applications · 4 items

UsesPyronin Y is a cationic dye that intercalates RNA and is visible as a red band during electrophoresis. It has also been shown to accumulate in mitochondria of viable cells. In conjuction with Methyl Green or Nancy-520, Pyronin Y can be used as a fluorescent differential stain of nucleic acids in paraffin tissue sections.

UsesPyronin Y has been used: in the purification of quiescent and cycling hematopoietic stem cells and staining of bone marrow cells (HSCs)as a component of the polychlorinated biphenyls (PCBS) solution for staining mammary gland side population cells (MG-SPs)staining of CD34+ cells

UsesBacterial and biological stain.

General DescriptionPyronin Y (C.I. 45005) is an aminoxanthene dye that is present as a weakly lipophilic cation in neutral aqueous solutions. It is also known as pyronine G.

Suppliers100 total

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Biological Applications
Antimalarial agent; antiviral agent; nucleic acid sequencing; treating protozoan infections; herbicides
Major Application
diagnostic assay manufacturinghematologyhistology
InChI
1S/C17H19N2O.ClH/c1-18(2)14-7-5-12-9-13-6-8-15(19(3)4)11-17(13)20-16(12)10-14;/h5-11H,1-4H3;1H/q+1;/p-1
InChIKey
INCIMLINXXICKS-UHFFFAOYSA-M
SMILES
[Cl-].CN(C)c1ccc2C=C3C=C\C(C=C3Oc2c1)=[N+](/C)C
CAS DataBase Reference
92 · 92-32-0
FDA UNII
659 G165T1 · W659G165T1
EPA Substance Registry System
Pyronine Y (92-32-0)
UNSPSC Code
41116130 · 41116130
NACRES
52 · NA.52
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
341 b · H341b
Precautionary statements
201 · P201-P202-P281-P308+P313-P403-P501c
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xn,Xi
Risk Statements
68 · 68-36/37/38
Safety Statements
22 · 22-24/25-36-26
WGK Germany
3 · 3
RTECS
1450000 · BQ1450000
TSCA
TSCA listed
HS Code
32041300 · 32041300
Storage Class
11 · 11 - Combustible Solids
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
Xn,Xi
safety_code
22-24/25-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H341b
Precautionary statements
P201-P202-P281-P308+P313-P403-P501c
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Additional notes

DefinitionChEBI: An organic chloride salt having 6-(dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium as the cation. Used with methyl green to selectively demonstrate RNA (red) in contrast to DNA (green) with the Unna Pappenheim method.