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Environmental fate & pathways

Bioaccumulation: aquatic / sediment

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Reference
Endpoint:
bioaccumulation in aquatic species, other
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Estimated data generated using the EPI Suite program developed by the USEPA.
Qualifier:
according to guideline
Guideline:
other: Modeling database
Principles of method if other than guideline:
Prediction done using BCFBAF (v3.01) model
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of test material: 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ilydene) methyl]-2-methyl - benzenamine hydrochloride
- IUPAC name:(4-(4-aminophenyl)(4-imino -cyclohexa-2,5-dienylidene) methyl)-2-methylaniline hydrochloride
- Molecular formula: C20H19N3.ClH
- Molecular weight: 337.852 g/mole
- Smiles notation: C(\c1cc(c(N)cc1)C) (c1ccc(N)cc1) =C1/C =CC(=N)C=C1.Cl
- InChl: 1S/C20H19N3.ClH/c1-13-12-16 (6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12, 21H, 22-23H2,1H3;1H/b20-14-,21-17?;
- Substance type: Organic
- Physical state: Solid
Radiolabelling:
not specified
Vehicle:
not specified
Test organisms (species):
other: Fish
Route of exposure:
aqueous
Test type:
static
Water / sediment media type:
natural water: freshwater
Test temperature:
25 deg.C
Reference substance (positive control):
not specified
Key result
Temp.:
25 °C
Type:
BCF
Value:
3.162 L/kg
Basis:
whole body w.w.
Calculation basis:
other: estimated
Remarks on result:
other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

==============================

SMILES : Cc1cc(ccc1N)C(=C2C=CC(N(CL)(H)(H)(H))C=C2)c3ccc(N)cc3

CHEM : Benzenamine, 4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)m

ethyl]-2-methyl-, monohydrochloride

MOL FOR: C20 H22 CL1 N3

MOL WT : 339.87

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.0665 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.21 (BAF = 1.62 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 0.98

Equation Used to Make BCF estimate:

Log BCF = 0.50 (Ionic; Log Kow dependent)

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet-wt)

Validity criteria fulfilled:
not specified
Conclusions:
The bioconcentration factor (BCF) of (4-(4-aminophenyl)(4-iminocyclohexa-2,5-dienylidene)methyl)-2-methylaniline hydrochloride was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which dose not exceed the bio concentration threshold of 2000, indicating that the chemical is expected to non bioaccumulate in the food chain.
Executive summary:

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical (4-(4-aminophenyl) (4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride (632 -99 -5). The bioconcentration factor (BCF) of (4-(4-aminophenyl) (4-iminocyclohexa -2,5-dienylidene)methyl) -2-methylaniline hydrochloride was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which not exceed the bio concentration threshold of 2000, indicating that the chemical (4-(4-aminophenyl)(4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride is expected to non bioaccumulate in the food chain.

Description of key information

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical (4-(4-aminophenyl) (4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride (632 -99 -5). The bioconcentration factor (BCF) of (4-(4-aminophenyl)(4-iminocyclohexa -2,5-dienylidene)methyl) -2-methylaniline hydrochloride was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which not exceed the bio concentration threshold of 2000, indicating that the chemical (4-(4-aminophenyl)(4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride is expected to non bioaccumulate in the food chain.

 

Key value for chemical safety assessment

BCF (aquatic species):
3.162 L/kg ww

Additional information

Various predicted data for the target compound (4-(4-aminophenyl)(4-imino -cyclohexa-2,5-dienylidene) methyl)-2-methylaniline hydrochloride (CAS No. 632-99-5) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In a prediction done using BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical (4-(4-aminophenyl) (4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride (632 -99 -5). The bioconcentration factor (BCF) of (4-(4-aminophenyl)(4-iminocyclohexa -2,5-dienylidene)methyl) -2-methylaniline hydrochloride was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which not exceed the bio concentration threshold of 2000, indicating that the chemical (4-(4-aminophenyl)(4-iminocyclohexa-2,5- dienylidene)methyl)-2-methylaniline hydrochloride is expected to non bioaccumulate in the food chain.

 

In a second predicted report, Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor over the pH scale 6, 7, 8 of the test substance (4-(4-aminophenyl)(4-iminocyclohexa- 2,5-dienylidene) methyl) -2-methylaniline hydrochloride (632 -99 -5) estimated to be 1, 1.52, 2.52 respectively. This value indicates that the test substance (4-(4-aminophenyl)(4-iminocyclohexa-2,5-dienylidene) methyl) -2-methylaniline hydrochloride was non-accumulative in aquatic organisms.

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical)  the bioaccumulation i.e BCF for test substance (4-(4-aminophenyl) (4-iminocyclohexa-2,5- dienylidene) methyl)-2-methylaniline hydrochloride was estimated to be 21.8 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance (4-(4-aminophenyl)(4-iminocyclohexa-2,5- dienylidene) methyl)-2-methylaniline hydrochloride is non- bioaccumulative in nature.

 

Similarly in a supporting weight of evidence study from authoritative database J-CHECK, 2017 for the read across chemical 4-[4-(dimethylamino) benzene- carboximidoyl]-N,N- dimethylaniline hydrochloride, Bioaccumulation test was conducted for 6 weeks for determination the bioconcentration factor (BCF) of substance 4-[4-(dimethylamino)benzenecarboximidoyl]-N,N- dimethylaniline hydrochloride (CAS no 2465-27-2) on test organism Cyprinus carpio. Recovery ratio : Test water : 1st concentration area : 90.2 % , 2nd concentration area : 90.0% Fish : 54.0%, ­ Limit of detection :  Fish : 0.012 microg/g And Nominal concentrations used in the study as - 1st Concentration area: 0.1 mg/L, 2nd Concentration area : 0.01 mg/L and Range finding study was carried out on Rice fish (Oryzias latipes) TLm(48h) 5 .3 ppm(w/v). Thus according to static Fish Test the BCF value for test substance4-[4-(dimethylamino) benzene-carboximidoyl] -N,N-dimethylaniline hydrochloride was observed to be 3.8-11 L/kg at dose concentration 0.1 ppm(w/v) and 6.1-16 L/kg at dose concentration 0.01 ppm(w/v) on test organism Cyprinus carpio during 6 weeks period. These BCF values indicate that the substance 4-[4 -(dimethylamino) benzenecarboximidoyl]-N,N-dimethylaniline hydrochloride is not bioaccumulative in fish and food chain.

 

For the read across chemical (569-64-2) HSDB, 2017, The BCF value of chemical 4-[(4-dimethyl-aminophenyl)-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]- dimethylazanium chloride (CAS no. 569-64-2) was estimated is 3 dimensionless by using log Kow of 0.62 and regression derived equation and it is far less than 2000 so it is concluded that this chemical is non bioaccumulative.

 

On the basis of above results for target chemical (4-(4-aminophenyl)(4-imino -cyclohexa-2,5-dienylidene) methyl)-2-methylaniline hydrochloride (from EPI suite, ACD labs and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK and HSDB, 2017), it can be concluded that the BCF value of test substance (4-(4-aminophenyl)(4-imino -cyclohexa-2,5-dienylidene) methyl)-2-methylaniline hydrochloride ranges from 0.62-21.8 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical (4-(4-aminophenyl)(4-imino -cyclohexa-2,5-dienylidene) methyl)-2-methylaniline hydrochloride is not expected to bioaccumulate in the food chain.