Decynium-22

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Decynium-22
The chemical structure of decynium-22
Names
Preferred IUPAC name
1-Ethyl-2-[(E)-(1-ethylquinolin-2(1H)-ylidene)methyl]quinolin-1-ium iodide
Other names
  • Decynium-22
  • Pseudocyanine iodide
  • Pseudoisocyanine iodide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.012.324 Edit this at Wikidata
EC Number
  • 213-556-6
UNII
  • InChI=1S/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
    Key: GMYRVMSXMHEDTL-UHFFFAOYSA-M
  • InChI=1/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
    Key: GMYRVMSXMHEDTL-REWHXWOFAU
SMILES
  • CCN1C(=CC2=[N+](C3=CC=CC=C3C=C2)CC)C=CC4=CC=CC=C41.[I-]
Properties
C23H23IN2
Molar mass 454.355 g·mol−1
Appearance Dark red powder
Melting point 273 °C (523 °F; 546 K)
Solubility 4.54 mg/ml in DMSO
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Decynium-22 is a

monoamine transporters such as the dopamine transporter and norepinephrine transporter.[2]

Transporter inhibition

Decynium has been shown to have a very high affinity to organic cation transporters in a variety of species, including human,[3][4] rat,[5] and pig.[6] Decynium-22 has been shown to block the uptake of the neurotoxin

astrocytes.[7]

Fluorescence

Decynium-22 emits a low

excitation spectrum of these aggregates. Decynium-22 fluorescence caused by aggregation can be observed in astrocytes.[2]

Schizophrenia and depression

Decynium-22 has recently been investigated for its role in increasing

5-HT transporter
(SERT), although it is also taken up by auxiliary transporters, known as "uptake 2", which include OCT and PMAT.

The most commonly prescribed antidepressant drugs are the

knock-out mice, which resulted in an improvement of social behavior.[11] When OCT3 was knocked out in mice, however, decynium-22 was ineffectual, indicating that the anti-depressant effects of decynium-22 are dependent upon its blockage of the OCT3.[10]

References

  1. ^ "Decynium-22". University of California, San Francisco. Archived from the original on 17 October 2014. Retrieved 16 Oct 2014.
  2. ^
    PMID 23875515
    .
  3. S2CID 6093183
    .
  4. PMID 12110607
    .
  5. S2CID 659539
    .
  6. PMID 9099681
    .
  7. PMID 12485400
    .
  8. ^ Stiel H, Daehne S, Teuchner K. J-aggregates of pseudoisocyanine in solution: New data from nonlinear spectroscopy. J Lumines. 1988;39:351–357.
  9. ^ Struganova IA. Dynamics of formation of 1,1′-diethyl-2,2′-cyanine iodide J-aggregates in solution. J Physical Chem A. 2000;104:9670–9674.
  10. ^
    PMID 23785165
    .
  11. PMID 6860
    .
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