1,1',3,3,3',3'-Hexamethylindodicarbocyanine iodide
Basic information
- CAS
36536-22-8- Standard SMILES
CN1C(=CC=CC=CC2=[N+](C)c3ccccc3C2(C)C)C(C)(C)c2ccccc21.[I-]- InChIKey
UANMYOBKUNUUTR-UHFFFAOYSA-M- Molecular formula
- C27H31IN2
- Average molar mass
- 510.5 g/mol
- Monoisotopic mass
- 510.1532
Names & identifiers
- Preferred name
- 1,1',3,3,3',3'-Hexamethylindodicarbocyanine iodide
- IUPAC
- 1,3,3-trimethyl-2-[5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]indole iodide
- English name
- Hexacyanine 2
- Molecular formula
- C27H31IN2
- Molecular weight
- 510.45
Names & synonyms
36536-22-81,1',3,3,3',3'-Hexamethylindodicarbocyanine iodideSNC-62H8U2C7F2NDTXSID70884814NK-5293H-Indolium, 2-(5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl)-1,3,3-trimethyl-, iodide (1:1)3H-Indolium, 2-[5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3-pentadienyl]-1,3,3-trimethyl-, iodide3H-Indolium, 2-(5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3-pentadienyl)-1,3,3-trimethyl-, iodide3H-Indolium, 2-[5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1,3,3-trimethyl-, iodide (1:1)RefChem:505730DTXCID601024235
Show more names
HIDCHidciPk 6433,3-trimethyl-nyl]-iodideHEXAMETHYLINDODICARBOCYANINE IODIDE1,1',3,3,3',3'-hexamethylindocarbocyanine iodide
253-091-6Hexacyanine 2DiIC1(5)2-[5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)penta-1,3-dienyl]-1,3,3-trimethyl-3H-indolium iodideHIDC iodide1,3,3-Trimethyl-2-(5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-3H-indol-1-ium iodideCyanine5 dimethylorb1693220
Database identifiers
- CAS
36536-22-8- PubChem CID
- 119007
- DTXSID
DTXSID70884814- UNII
- 2H8U2C7F2N
- EC Number
- 253-091-6
Properties
Computed structural properties
- Topological polar surface area
- 6.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 689
Physicochemical properties
- Melting point
- 264 °C · 264 °C (dec.)(lit.)
- Density
- 1.2991 · 1.2991 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in methanol, dimethyl sulfoxide; partially soluble in water
- form
- crystals
- color
- Blue green
- Appearance
- Dark blue solid
- ex/em
- 638 · 638/658 nm (MeOH)
- λmax
- 638 nm · 638 nm
- Biological Applications
- Measuring membrane potential; detecting prostate cancer; analyzing urine; apoptosis assays; in vivo hematotoxicity assays
- InChI
- InChI=1S/C27H31N2.HI/c1-26(2)20-14-10-12-16-22(20)28(5)24(26)18-8-7-9-19-25-27(3,4)21-15-11-13-17-23(21)29(25)6;/h7-19H,1-6H3;1H/q+1;/p-1
- InChIKey
- UANMYOBKUNUUTR-UHFFFAOYSA-M
- SMILES
- C12C=CC=CC=1N(/C(=C\C=C\C=C\C1C(C)(C)C3C=CC=CC=3[N+]=1C)/C2(C)C)C.[I-]
- FDA UNII
- 2 H8U2C7F2N · 2H8U2C7F2N
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 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.5%)
Safety data
- tsca
- TSCA listed
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 24/25-36-26
- Hazard statements
- H312-H302-H332-H335-H315-H319
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Uses & manufacturing
General Manufacturing Information3H-Indolium, 2-[5-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1,3,3-trimethyl-, iodide (1:1): INACTIVE
Applications
DescriptionHIDC iodide is a carbocyanine dye that stains mitochondria of live cells.
UsesHexacyanine 2 is a known synthetic biological stain that is used in photodynamic therapy. Recent research has focused on the development of the combination of a photosensitizer with photoprotector cyanine dye as a novel antitumor strategy for the eradication of malignant cells expressing the multidrug-resistance phenotype.
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Compound notes
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