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Hydrolysis

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Reference
Endpoint:
hydrolysis
Type of information:
(Q)SAR
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification
Justification for type of information:
Data is from OECD QSAR toolbox version 3.3 and the QMRF report has been attached.
Reference:
Composition 0
Qualifier:
according to
Guideline:
other: Estimated data
Principles of method if other than guideline:
Prediction was done using the OECD QSAR toolbox version 3.3.
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material : 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride
- Molecular formula : C24H30Cl2N2
- Molecular weight : 417.421 g/mol
- Smiles notation : C1(=[N+](c2ccccc2C1(C)C)C)\C=C/c1c(cc(N(CCCl)CC)cc1)C.[ClH-]
- InChl : 1S/C24H30ClN2.ClH/c1-6-27(16-15-25)20-13-11-19(18(2)17-20)12-14-23-24(3,4)21-9-7-8-10-22(21)26(23)5;/h7-14,17H,6,15-16H2,1-5H3;1H/q+1;/p-1
- Substance type: Organic
- Physical state: Solid
Radiolabelling:
not specified
Analytical monitoring:
not specified
Details on sampling:
No data available
Buffers:
No data available
Estimation method (if used):
No data available
Details on test conditions:
No data available
Number of replicates:
No data available
Positive controls:
not specified
Negative controls:
not specified
Statistical methods:
No data available
Preliminary study:
No data available
Test performance:
No data available
Transformation products:
not specified
Details on hydrolysis and appearance of transformation product(s):
No data available
Key result
Half-life:
147.899 d
Type:
not specified
Remarks on result:
other: Non hydrolysable
Other kinetic parameters:
No data available
Details on results:
No data available
Results with reference substance:
No data available

Estimation method: Takes average value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

(((((((("a" or "b" or "c" )  and "d" )  and ("e" and ( not "f") )  )  and "g" )  and "h" )  and "i" )  and "j" )  and ("k" and "l" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as SN2 AND SN2 >> Alkylation, direct acting epoxides and related after cyclization AND SN2 >> Alkylation, direct acting epoxides and related after cyclization >> Nitrogen Mustards by DNA binding by OASIS v.1.3

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine AND SN2 AND SN2 >> Episulfonium Ion Formation AND SN2 >> Episulfonium Ion Formation >> Mustards by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as SN2 AND SN2 >> Nucleophilic substitution at sp3 carbon atom AND SN2 >> Nucleophilic substitution at sp3 carbon atom >> Alkyl halides  by Protein binding by OASIS v1.3

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Not calculated by Hydrolysis half-life (Ka, pH 8)(Hydrowin) ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Halogens AND Non-Metals by Groups of elements

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Metalloids by Groups of elements

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Moderate by Hydrolysis half-life (pH 6.5-7.4) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Moderate by Hydrolysis half-life (pH 6.5-7.4) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Moderate by Hydrolysis half-life (pH 6.5-7.4) ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "k"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 188 Da

Domain logical expression index: "l"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 474 Da

Validity criteria fulfilled:
not specified
Conclusions:
The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4-[(2-chloroethyl)- ethylamino] -o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was non hydrolysable.
Executive summary:

Hydrolysis of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) was predicted using OECD QSAR toolbox version 3.3 (2017). The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4-[(2-chloroethyl)- ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was non hydrolysable.

Description of key information

Hydrolysis of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) was predicted using OECD QSAR toolbox version 3.3 (2017). The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4- [(2-chloroethyl)- ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was non hydrolysable.

Key value for chemical safety assessment

Half-life for hydrolysis:
147.8 d

Additional information

Hydrolysis:

Various predicted and experimental data for the target compound 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]- 1,3,3-trimethyl-3H-indolium chloride (CAS No. 6441 -82 -3) and supporting weight of evidence studies for its closest read across substance with logKow as the primary descriptor were reviewed for the hydrolysis end point which are summarized as below:  

 

In the first weight of evidence study, hydrolysis of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) was predicted using OECD QSAR toolbox version 3.3 (2017). The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4- [(2-chloroethyl)- ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was non hydrolysable.

Similarly second study was conducted on the read across chemical which was selected on the basis of logKow as the primary descriptor. Chemical 1,2,3-Trichloropropane (96-18-4) from authoritative database study was conducted for the estimation of hydrolysis rate constant and Half-life of hydrolysis at pH 7 of test chemical 1,2,3-Trichloropropane by base catalyzed first order reaction and structure estimation method. The hydrolysis rate constant of chemical 1,2,3-Trichloropropane was 1.8X10-6 /h based on the first order reaction. The half-life of hydrolysis obtained at pH 7 was 44 years. Since half-life of hydrolysis at pH is more than 10 days so it is concluded that test chemical 1,2,3-Trichloropropane was non hydrolyzing.

 

Similarly thirdstudy was conducted on another read across chemical 1,2-Dibromethan (106-93-4) which was selected on the basis of logKow as the primary descriptor. To estimate hydrolysis rate constant and Half-life of hydrolysis at pH 7 of test chemical 1,2-Dibromethan at 60degree C. The aqueous hydrolysis rate constant for ethylene dibromide was measured at pH 7 to be 0.00187/hr at 60 deg C. The half-life of 1,2-Dibromethan obtained at pH 7 was 15.44 days. Since half-life of hydrolysis at pH 7 is more than 10 days so it is concluded that test chemical 1,2-Dibromethan was non hydrolyzing.

 

Thus based on the above data for the target chemical and read across chemical it was concluded that the chemical was not hydrolysable as it exceeds the half-life of at pH 7 is more than 10 days.