DAMINOZIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H12N2O3
Molecular Weight	160.1711
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)NC(=O)CCC(O)=O

InChI

InChIKey=NOQGZXFMHARMLW-UHFFFAOYSA-N

InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)

HIDE SMILES / InChI

Molecular Formula	C6H12N2O3
Molecular Weight	160.1711
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://archive.epa.gov/pesticides/reregistration/web/pdf/0032fact.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22724510

Daminozide, also known as Alar, is a systemic growth regulator registered for use on ornamentals, including potted chrysanthemums and poinsettias, and bedding plants in enclosed structures such as greenhouses, shadehouses, and interiorscapes. It retards stem growth, protects against heat, drought, and frost, and induces the development of multiple flowers. In 1963 it was registered in the USA as a pesticide for use on potted chrysanthemums. In 1968 its use on apples was registered. After toxicology studies, conducted by EPA, demonstrated that daminozide and its metabolites were oncogenic in multiple species and strains of test animals, the use of daminozide on food was discontinued. Later it was found that daminozide is a selective inhibitor of human KDM2/7 histone demethylases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histone lysine demethylase PHF8 1 Target ID: CHEMBL1938212 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22724510	Inhibitor 8297		550.0 nM [IC50]
Lysine-specific demethylase 2A 3 Target ID: CHEMBL1938210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22724510	Inhibitor 8297		1500.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Determination of daminozide residues in apple pulp using HPLC-DAD-UV.	2001 Aug	11513626
The work environment impact assessment: a methodologic framework for evaluating health-based interventions.	2001 Feb	11170164
Transformation of the plant growth regulator daminozide (Alar) and structurally related compounds with CuII ions: oxidation versus hydrolysis.	2003 May 1	12775054
Gibberellin inhibitors improve embryogenic tissue initiation in conifers.	2005 Feb	15688237
Perils of paradigm: complexity, policy design, and the Endocrine Disruptor Screening Program.	2005 Feb 8	15701170
Validation of a fast and easy method for the determination of residues from 229 pesticides in fruits and vegetables using gas and liquid chromatography and mass spectrometric detection.	2005 Mar-Apr	15859089
Heterogeneous photocatalysed degradation of two selected pesticide derivatives, triclopyr and daminozid in aqueous suspensions of titanium dioxide.	2006 Jul	16359776
Categorizing mistaken false positives in regulation of human and environmental health.	2007 Feb	17362413
Quartz crystal microbalance for the determination of daminozide using molecularly imprinted polymers as recognition element.	2007 Jan 15	16621501
Is gene activity in plant cells affected by UMTS-irradiation? A whole genome approach.	2008	21918607
Influence of gibberellin and daminozide on the expression of terpene synthases and on monoterpenes in common sage (Salvia officinalis).	2010 Jul 1	20163890
Further analysis of Ames-negative rodent carcinogens that are only genotoxic in mammalian cells in vitro at concentrations exceeding 1 mM, including retesting of compounds of concern.	2010 Nov	20720197
Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone demethylases.	2012 Jul 26	22724510

Patents

Sample Use Guides

In Vivo Use Guide

Carcinogenicity of daminozide was studied in mice and rats after oral administration at doses 5,000 or 10,000 ppm.

Route of Administration: Oral

In Vitro Use Guide

Detection of catalytic turnover of methyl-lysine peptide substrates was performed using the lysine demethylase AlphaScreen. The enzyme reaction uses a biotinylated peptide substrate and detection of the biotinylated product is achieved using a methyl mark specific antibody coupled to a protein-A acceptor bead and a streptavidin donor bead that captures the biotin. Upon excitation at 680 nM singlet oxygen is generated by the donor bead and emission of the luminescent signal from the acceptor bead is measured at 520 – 620 nM. Enzyme reactions and subsequent detection of the product were performed in assay buffer consisting of 50 mM HEPES pH 7.5, BSA (0.1% w/v) and Tween-20 (0.01% v/v).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:11 UTC 2023` Edited by `admin` on `Fri Dec 15 15:05:11 UTC 2023`
Record UNII	F6KF33M5UB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAMINOZIDE

Common Name

English

2,2-DIMETHYLHYDRAZINE SUCCINIC ACID

Systematic Name

English

SUCCINIC ACID 2,2-DIMETHYLHYDRAZIDE

Common Name

English

DAMINOZIDE [HSDB]

Common Name

English

B-9

Code

English

BUTANEDIOIC ACID MONO(2,2-DIMETHYLHYDRAZIDE)

Common Name

English

B-995

Code

English

N-(DIMETHYLAMINO)SUCCINAMIC ACID

Systematic Name

English

ALAR

Common Name

English

DAMINOZIDE [ISO]

Common Name

English

DAMINOZIDE [MI]

Common Name

English

1-(2,2-DIMETHYLHYDRAZIDE)BUTANEDIOIC ACID

Common Name

English

SUCCINIC ACID, 2,2-DIMETHYLHYDRAZIDE

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

35101