Page last updated: 2024-12-06

tetracyanoquinodimethane

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Tetracyanoquinodimethane (TCNQ) is an organic compound with the formula C12H4N4. It is a strong electron acceptor and is used in the synthesis of organic conductors and superconductors. TCNQ is a dark purple solid that is soluble in polar solvents. It is synthesized by the reaction of p-benzoquinone with malononitrile. TCNQ has been studied extensively due to its ability to form charge-transfer complexes with various electron donors. These complexes have a wide range of electrical and magnetic properties, making them attractive for applications in electronics and materials science. TCNQ is also used in the preparation of organic solar cells and organic light-emitting diodes.'

tetracyanoquinodimethane: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tetracyanoquinodimethane : A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID73697
CHEBI ID52445
SCHEMBL ID51181
MeSH IDM0061666

Synonyms (73)

Synonym
c12h4n4
2,5-cyclohexadiene-delta1,alpha:4,alpha'-dimalononitrile
7,7,8,8-tetracyano-1,4-quinodimethan
nsc 105237
2,5-cyclohexadiene-delta(sup 1,alpha:4,alpha)-dimalononitrile
2,5-cyclohexadiene-delta(sup1alpha:4alpha)dimalononitrile
einecs 216-174-8
2,2'-(2,5-cyclohexadiene-1,4-diylidene)bismalononitrile
2,5-cyclohexadiene-1,4-diylidenedimalononitrile
7,7,8,8-tetracyano-p-quinodimethane
2,5-cyclohexadiene-.delta.1,.alpha.:4,.alpha.'-dimalononitrile
propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-
1518-16-7
7,8,8'-tetracyanoquinodimethane
tetracyano-p-quinodimethane
nsc105237
nsc-105237
7,8,8-tetracyanoquinodimethane
quinodimethan, tetracyano-
tetracyanoquinodimethan(e)
2,4-diylidenedimalononitrile
tcnq
propanedinitrile,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-
7,8,8-tetracyano-p-quinodimethane
2,.alpha.:4,.alpha.'-dimalononitrile
2,5-cyclohexadiene-.delta.(sup1.alpha.:4.alpha.)dimalononitrile
tetracyanoquinodimethan
tetracyanoquinodimethane
7,8,8-tetracyano-1,4-quinodimethan
7,7,8,8-tetracyanoquinodimethane, 98%
7,7,8,8-tetracyanoquinodimethane
MAYBRIDGE1_002049
NCIOPEN2_007109
SR-01000635718-1
CHEBI:52445
2,2'-cyclohexa-2,5-diene-1,4-diylidenedipropanedinitrile
2,5-cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile
7,7',8,8'-tetracyanoquinodimethane
HMS547F03
2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
1,4-bis(dicyanomethylene)cyclohexadiene
T0078
A809224
2-[4-(dicyanomethyliden)cyclohexa-2,5-dien-1-yliden]propandinitril
CCG-45987
unii-hc6fb4h2kw
hc6fb4h2kw ,
2,2'-(cyclohexa-2,5-diene-1,4-diylidene)dimalononitrile
FT-0621330
AKOS015890682
SCHEMBL51181
T3034
DTXSID5061748
W-108059
2,5-cyclohexadiene-1,4-diylidene-.alpha.,.alpha.'-dimalononitrile
mfcd00011664
(2,5-cyclohexadiene-1,4-diylidene)-dimalononitrile
2-(4-dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile
CS-W015411
(2,5-cyclo-hexadiene-1,4-diylidene)-dimalononitrile
(2,5-cyclohexadiene-1,4-diylidene)malononitrile
(2,5-cyclohexadiene-1,4-diylidene)dimalononitrile
quinodimethane, tetracyano-
2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis(propanedinitrile)
7,7,8,8-tetracyano-1,4-quinodimethane
7,7,8,8-tetracyanoquinodimethane (purified by sublimation)
Q2135917
CS-17370
D77779
26810-79-7
YSWG203
SB66414
SY009883

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"A simple and rapid spectrophotometric procedure has been developed for the determination of four local anaesthetics containing a free primary amine moiety and of procainamide hydrochloride as the drug substances and in dosage forms."( Use of 7,7,8,8-tetracyanoquinodimethane for spectrophotometric determination of certain local anaesthetics and procainamide hydrochloride.
Hassan, HY; Hussein, SA; Mohamed, AM; Mohamed, HA, 1991
)
0.63
" The proposed methods were applied successfully to the determination of the different penicillins investigated, either in pure or dosage forms, with good accuracy and precision."( Utility of certain pi-acceptors for the spectrophotometric determination of some penicillins.
Askal, HF; Omar, NM; Saleh, GA, 1991
)
0.28
" The spectrophotometric and the atomic absorption spectrometric procedures hold well their accuracy and precision when applied to the analysis of cefotaxime sodium and cefuroxime sodium dosage forms."( Spectrophotometric and atomic absorption spectrometric determination of certain cephalosporins.
Abdellatef, HE; Ayad, MM; Elsaid, HM; Shalaby, AA, 1999
)
0.3
" The proposed method has been applied to the determination of these drugs in their each pharmaceutical dosage forms with satisfactory results."( Study on the charge-transfer reaction between 7,7,8,8-tetracyanoquinodimethane and drugs.
Bian-zhen, X; Feng-lin, Z; Shen-yang, T; Zhi-quan, Z, 1999
)
0.55
" The developed methods were applied successfully for the determination of the studied drugs in their pharmaceutical dosage forms with a good precision and accuracy compared to official and reported methods as revealed by t- and F-tests."( Spectrofluorimetric study of the charge-transfer complexation of certain fluoroquinolones with 7,7,8,8-tetracyanoquinodimethane.
Du, LM; Fu, M; Yao, HY, 2005
)
0.54
" Both the methods have been applied to the determination of lisinopril in pharmaceutical dosage forms."( Application of pi-acceptors to the spectrophotometric determination of lisinopril in commercial dosage forms.
Anwar, N; Kashif, M; Rahman, N,
)
0.13
" The method is applicable for the assay of the investigated drugs in different dosage forms and the results are in good agreement with those obtained by the official method."( Utility of 7,7,8,8-tetracyanoquinodimethane charge transfer reagent for the spectrophotometric determination of trazodone, amineptine and amitriptyline hydrochlorides.
El-Dien, FA; Mohamed, GG; Mohamed, NA, 2007
)
0.67
" The proposed methods were validated according to ICH guidelines and were successfully applied for the determination of VN and NF in their tablet dosage forms."( Application of π acceptors to the spectrophotometric and spectrofluorimetric determination of vincamine and naftidrofuryl oxalate in their pharmaceutical preparations.
Badr El-Dien, MM; Elbrashy, AM; Ibrahim, FA; Nasr, JJM, 2017
)
0.46
" Using these complexes, the quantitative determination of KT in its dosage form was successful."( Charge Transfer Complexes of Ketotifen with 2,3-Dichloro-5,6-dicyano-
AlMasoud, N; AlRabiah, H; Bakheit, A; Mostafa, GAE, 2021
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
alicyclic compoundAn aliphatic compound having a carbocyclic ring structure which may be saturated or unsaturated, but may not be a benzenoid or other aromatic system.
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
quinodimethaneA dimethylidenecyclohexadiene, formally derived from benzoquinone by replacement of both of the quinone oxygens by methylidene groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (155)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (4.52)18.7374
1990's22 (14.19)18.2507
2000's52 (33.55)29.6817
2010's62 (40.00)24.3611
2020's12 (7.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.26 (24.57)
Research Supply Index5.10 (2.92)
Research Growth Index5.04 (4.65)
Search Engine Demand Index51.64 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.62%)5.53%
Reviews2 (1.23%)6.00%
Case Studies1 (0.62%)4.05%
Observational0 (0.00%)0.25%
Other158 (97.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]