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Details

Stereochemistry ACHIRAL
Molecular Formula C8H5Cl2O3.Na
Molecular Weight 243.019
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,4-D-SODIUM

SMILES

[Na+].[O-]C(=O)COC1=CC=C(Cl)C=C1Cl

InChI

InChIKey=RFOHRSIAXQACDB-UHFFFAOYSA-M
InChI=1S/C8H6Cl2O3.Na/c9-5-1-2-7(6(10)3-5)13-4-8(11)12;/h1-3H,4H2,(H,11,12);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H5Cl2O3
Molecular Weight 220.03
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

2,4-Dichlorophenoxyacetic acid (2,4-D) was the first synthetic herbicide to be commercially developed and has commonly been used as a broadleaf herbicide for over 60 years. It is a selective herbicide that kills dicots without affecting monocots and mimics natural auxin at the molecular level. 2,4-D was developed during World War II as one of many so-called phenoxy herbicides by aiming to increase crop yields for a nation at war. It was commercially released in 1946 becoming the first successful selective herbicide and allowed for greatly enhanced weed control in wheat, maize, rice, and other similar cereal crops because it specifically targets dicots. This herbicide family is said to have “initiated an agricultural revolution and laid the corner stone of present-day weed science” when it was first marketed in the 1940s.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
463.0 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Neonate rats were treated with 2,4-dichlorophenoxyacetic acid (2,4-D) from the 7th or 12th until the 17th or 25th postnatal day. Two drug dosages were used: 70 and 100 mg/kg body weight of 2,4-D. At the 17th day of age, no changes were observed in body weight, protein and DNA content. However, 25-day-old treated pups showed diminutions in body and brain weight, protein and DNA levels, depending on doses and period of treatment.
Route of Administration: Oral
In Vitro Use Guide
Different doses of 2,4-D (10 nM, 100 nM, 1 uM, 10 uM, 100 uM, and 200 uM) were applied to human spermatozoa prepared from normal fresh semen samples. The results indicated that 2,4-D did not affect the viability, capacitation, or spontaneous acrosome reactions of human spermatozoa, but it dose-dependently inhibited the total motility, progressive motility, ability to penetrate viscous medium, and progesterone-induced capacitation and acrosome reaction rates.
Substance Class Chemical
Record UNII
2H005922RS
Record Status Validated (UNII)
Record Version