3-aminomethyl-3,5,5-trimethylcyclohexylamine

PBT assessment

PBT assessment: overall result

PBT status:

the substance is not PBT / vPvB

Justification:

PBT / vPvB - Assessment for the parent compound

Based on the results and evidence set up in the PBT endpoint record, it can be concluded that the substance is considered to be potentially P/vP, from a precautionary point of view.

However, the substance is not B/vB based on a measured log Kow of 0.99 (Hüls Infracor GmbH 1998) for the substance. Considering all of the applied (Q)SAR models, the calculated BCF values range from 1.9 to 14.6 L/kg, indicating a low potential for bioaccumulation.

The substance is neither chronically nor acutely toxic to aquatic organisms.

Both the NOEC value from the Daphnia reproduction study and the NOEC value (growth rate) for freshwater alga are >=0.01 mg/L;

and substance is not classified as carcinogenic (category 1 or 2), mutagenic (category 1 or 2), or toxic for reproduction (category 1, 2 or 3) according to Directive 67/548/EEC or carcinogenic (category 1A or 1B), germ cell mutagenic (category 1A or 1B), or toxic for reproduction (category 1A, 1B or 2) according to Regulation EC No 1272/2008;

and no other evidence of chronic toxicity, as identified by the classifications T, R48 or Xn, R48 according to Directive 67/548/EEC or specific target organ toxicity after repeated exposure (STOT RE category 1 or 2) according to Regulation EC No 1272/2008

 

Overall, the substance is P/vP from a precautionary point of view, but not B/vB and not T, therefore it can be concluded that the substance is not PBT or vPvB.

 

PBT / vPvB – Assessment for modelled metabolites of (3-aminomethyl-3,5,5-trimethylcyclohexylamine (CAS 2855-13-2) (IPDA):

 

ECHA Guidance on information requirements and chemical safety assessment (v3.0, June 2017), Chapter R.11.4.1 specifies that “Constituents, impurities and additives should normally be considered relevant for the PBT/vPvB assessment when they are present in concentration of ≥ 0.1% (w/w)” […] “Similar arguments apply to relevant transformation/degradation products”.

In order to identify the relevant degradation products of (3-aminomethyl-3,5,5-trimethylcyclohexylamine (CAS 2855-13-2) as a standard information requirement according to Column 1, Section 9.2.3. of Annex IX to REACH and for purposes of an assessment of potential PBT/vPvB properties, the metabolites were modelled using CATALOGIC 301 C v .09.13 - June, 2016 (OASIS CATALOGIC v.5.11.19).

Overall, the CATALOGIC 301 C v .09.13 calculated 112 metabolites (Table) identifying 40 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥0.1%.

 

 

 

 

 

Table: QSAR prediction for CAS 2855-13-2 (3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA) using CATALOGIC 301 C v .09.13 - June, 2016;

metabolites with a quantity > 0. 1 % parent after 28 d are highlighted by bold type; metabolite no: according to (Q)SAR model Catalogic v09.13)

No	Metabolite no	Smiles	Level	Transformation no	Transformation name	Quantity (%)	Log Kow	BOD prediction % 80D (28 d)
1	13	CC1(C)CC(N)CC(C)(C(O )=O}C1	2	66	Aldehyde Oxidation	14,82	-1,06	9
2	Parent	CC1(C)CC(N)CC(C)(CN)C1	0			12,23	1,90	15
3	66	CC(C)(CC(C)(C)C(O)=O)C(O)=O	7	66	Aldehyde Oxidation	7,011	1,48	0
4	68	CC(C)(CC(C)(CC(O)=O)C(O)=O)C(O)=O	7	66	Aldehyde oxidation	10,56	0,73	0
5	57	CC(C)(C)CC(C)(CO)C(O)=O	6	346	Decarboxylation	6,41	1,84	1
6	35	CC/C)/CC/C)/CC/0)=0)CN)C/0)=0	4	66	Aldehvde Oxidation	5,713	-2,70	7
7	33	CC/C)/CC/O)=OlCC/C)/CN)C/0)=0	4	66	Aldehvde Oxidation	5,713	-2,70	22
8	46	CC(C)(CC(C)(C)CN)C(O)=O	5	346	Decarboxylation	4,54	-1,37	8
9	45	CC{C){C)CC{C){CN)C{O)=O	5	346	Decarboxylation	4,54	-1,37	22
10	107	CC(C)(C)C(O)=O	14	319	Decarboxylation	4,097	1,45	0
11	47	CC(C)(CC(O)=O)CC(C)(CO)C(0)=O	5	309	Ester hydrolysis	3,519	0,51	1
12	12	CC1(C)CC(C)(CN)CC( =O) OC1	2	184	Bayer-Villiger oxidation	2,192	0,95	13
13	11	CC1(C)CC(=O)OCC(C)(CN)C1	2	184	Bayer-Villiger oxidation	2,192	0,95	17
14	74	CC/Cl/CC/Cl/CO)C/Ol=OlC/O)=O	8	487	Methvl arouo oxidation	2,06	0,01	0
15	25	CC1(C(O)=O)CC(N)CC(C)(CN)C1	3	66	Aldehyde Oxidation	1,751	-2,54	18
16	38	CC1(C)CC( C)(C(O)=O)CC( =O)OC1	4	184	Bayer-Villiqer oxidation	1,37	1,18	8
17	37	CC1(C)CC(=O) OCC(C)(C(O)=O)C1	4	184	Bayer-Villiqer oxidation	1,37	1,18	5
18	73	CC{CC{C){C)C)C{O)=O	8	216	Decarboxylation	1,082	2,85	20
19	26	CC1(C)CC(N)CC(CN)(C(O)=O)C1	3	66	Aldehyde Oxidation	0,8757	-2,54	25
20	85	CC(=CC(C)(C)C)C(0)=0	10	315	Beta-oxidation	0,8469	2,76	29
21	90	CC(C(O)C(C)(C)C)C(O)=O	11	310	Beta-oxidation	0,7361	1,31	27
22	102	CC/C/=O)C/C)/C)C)C/O)=O	13	71	Keto-enol tautomerism	0,6399	0,80	41
23	77	CC(CC(O)=O)(CC(C)(CN)C(O)=O)C(O)=O	8	66	Aldehyde oxidation	0,4864	-3,94	36
24	60	CC(CC(O)=O)(CC{C)(CO)C(O)=O)CN	6	309	Ester hydrolysis	0,4158	-4,17	8
25	76	CC(CC(O)=O)(CC(C)(CO)C(O)=O)C(O)=O	8	487	Methyl group oxidation	0,3756	-0,73	0
26	112	CC/=C/O)C/C)(O)CC(O)=O)C/O)=O	16	315	Beta-oxidation	0,3542	-1,00	89
27	70	CC(C)(CC(C)(CO)C(O)=O)CN	7	346	Decarboxylation	0,3304	-2,83	7
28	105	CC(C)(C)CCC(O)=O	13	319	Decarboxylation	0,2703	2,43	32
29	104	CC(CC(C)(O)CC(O)=O)C(O)=O	13	216	Decarboxylation	0,2699	-0,44	66
30	79	CC(C)(CC(CC(O)=O)(CN)C(O)=O)C(O)=O	8	66	Aldehyde oxidation	0,2432	-3,94	25
31	61	CC(C)(CC(O)=O)CC(CN)(CO)C(O)=O	6	309	Ester hydrolysis	0,2079	-4,17	31
32	106	CC(C)(CC(=O)CC(O)=O)C(O)=O	13	340	Decarboxylation	0,1833	-0,95	28
33	71	CC(C)(C)CC(CN)(CO)C(0)=0	7	346	Decarboxylation	0,1652	-2,83	32
34	50	CC1{CN)CC{=O)OCC{C){C{O)=O)C1	5	184	Bayer-Villiaer oxidation	0,1618	-3,49	11
35	49	CC1/C/Ol=OlCC/=OlOCC/Cl/CNlC1	5	184	Baver-Villiaer oxidation	0,1618	-3,49	28
36	110	CC/C)/CO)C/O)=O	15	487	Methvl arouo oxidation	0,157	-0,02	0
37	101	CC(C)CC(CC(O)=O)C(O)=O	12	216	Decarboxylation	0,135	1,06	72
38	9	CC1(C)CC(N)C(=O )OC(C)(CN)C1	1	747	Bayer-Villiger oxidation	0,1068	-0,60	17
39	8	CC1 (C )CC( C)( CN)CC( N)C( =0)01	1	747	Bayer-Villiger oxidation	0,1068	-0,60	14
40	44	CC(C)(CC(=O)CC(C){O)C=O)C(O)=O	4	357	Oxidative deamination and N-dealkylation	0,0988	-1,21	34
41	41	CC(C)(O)CC(=O)CC{C){C=O)C{0)=0	4	357	Oxidative deamination and N-dealkylation	0,0988	-1,21	68
42	21	CC(C)(CC(N)CC(C)(O)CN)C(O)=O	2	309	Ester hydrolvsis	0,09499	-3,89	23
43	18	CC(C)(O)CC( N)CC(C)(CN)C(O)=O	2	309	Ester hydrolvsis	0,09499	-3,89	39
44	100	CC(C)(CC(O)(CC(O)=O)C(O)=O)C(O)=O	12	164	Beta-oxidation	0,08658	-0,61	25
45	52	CC1(C)CC{CN){C/O)=O)CC/=O)OC1	5	184	Bayer-Villiaer oxidation	0,08092	-3,49	31
46	51	CC1(C)CC(=O)OCC(CN)(C(O)=O)C1	5	184	Bayer-Villiaer oxidation	0,08092	-3,49	29
47	86	CC(CC(C)(CO)C(O)=O)(CO)C(O)=O	10	487	Methyl ciroup oxidation	0,07865	-1,04	0
48	91	CC(CC(C)(CC(O)=O)C(O)=O)C(O)=O	11	216	Decarboxylation	0,07059	0,28	34
49	64	CC(C)(C)CC(C)(O)C=O	6	357	Oxidative deamination and N-dealkylation	0,06711	1,09	25
50	63	CC(C)(O)CC(C)(C)C=O	6	357	Oxidative deamination and N-dealkylation	0,06711	1,09	8
51	109	CC(=CC(C)(O)CC(O)=O)C(O)=O	14	164	Beta-oxidation	0,0613	-0,53	70
52	32	CC( C)( CC(=O) CC(C)(0)CN)C( 0)=0	3	356	Oxidative deamination and N-dealkylation	0,05934	-4,39	23
53	29	CC( C)( O)CC( =O)CC(C)( CN)C( 0)=0	3	356	Oxidative deamination and N-dealkylation	0,05934	-4,39	45
54	1	CC1(C)CC(=O)CC(C)(CN)C1	1	762	Oxidative deamination and N-dealkylation	0,05626	1,40	28
55	111	CC(C(O)C(C)(O)CC(O)=O)C(O)=O	15	310	Beta-oxidation	0,05328	-1,57	74
56	43	CC(Cl{CC{O)=O)CC{Cl{O)CN	4	123	Decarboxvlation	0,05073	-2,83	20
57	42	CC(C)(O)CC(C)(CC(O)=O)CN	4	123	Decarboxylation	0,05073	-2,83	12
58	54	CC(C){C)CC(C)(O)CN	5	346	Decarboxylation	0,04031	1,11	18
59	53	CC(C)(O)CC(C)(C)CN	5	346	Decarboxylation	0,04031	1,11	13
60	10	CC1(C)CC(N)CC(C)(CN)OC1=O	1	747	Bayer-Villiger oxidation	0,0316	-0,60	25
61	7	CC1(C)CC(N)CC(C)(CN)C(=0)01	1	747	Bayer-Villiqer oxidation	0,0316	-0,60	44
62	6	CC1 (C)CC( C)( CN)CC( N)OC1=O	1	747	Bayer-Villiqer oxidation	0,0316	1,15	13
63	5	CC1(C)CC(N)OC(=O)C(C)(CN)C1	1	747	Bayer-Villiqer oxidation	0,0316	1,15	24
64	20	CC1(C)CC(=O)C(=O)OC(C)(CN)C1	2	356	Oxidative deamination and N-dealkylation	0,01975	0,93	24
65	19	CC1(C)CC( C)(CN)CC(=O)C(=0)01	2	356	Oxidative deamination and N-dealkylation	0,01975	0,93	16
66	81	CC(CC/CC/O)=O)/CO)C/O)=O)/CO)C/O)=O	9	488	Methvl arouo oxidation	0,01467	-1,49	0
67	80	CC(CC(O)=O)(CC(CO)(CO)C(O)=O)C(O)=O	9	488	Methyl ciroup oxidation	0,01467	-1,79	0
68	99	CC(C)(C)CC(C(O)=O)C(O)=O	12	66	Aldehyde oxidation	0,004702	1,03	37
69	97	CC(=CC(C)(CC(O)=O)C(O)=O)C(O)=O	12	315	Beta-oxidation	0,0004693	0,20	62
70	2	CC1(C)CC(N)CC(C)(C=O)C1	1	357	Oxidative deamination and N-dealkylation	0,000395	1,88	12
71	36	CC/C)/CC/C)/CC/O)=O)CN)C=O	4	93	Primarv hvdroxvl arouo oxidation	0,0001756	-2,37	10
72	34	CC/C)/CC/O)=OlCC/C)/CN)C=O	4	93	Primarv hvdroxvl arouo oxidation	0,0001756	-2,37	26
73	23	CC(C)(CC(C)(CC( O)=O)CN)CO	3	309	Ester hydrolvsis	0,0001756	-2,34	10
74	22	CC(C)(CC(O)=O)CC(C)(CN)CO	3	309	Ester hydrolvsis	0,0001756	-2,34	26
75	58	CC/Cl/CC/C)/CC/Ol=O)C/O)=O)C=O	6	93	Primarv hvdroxvl arouo oxidation	0,0001097	0,48	5
76	48	CC(C)(CC(C)(CC(O)=O)C(O)=O)CO	5	309	Ester hydrolvsis	0,0001097	0,51	5
77	56	CC(C)(CC(C)(C)C=O)C(O)=O	6	357	Oxidative deamination and N-dealkylation	0,00007558	1,81	5
78	55	CC(C)(C)CC(C)(C=O)C(0)=0	6	357	Oxidative deamination and N-dealkylation	0,00007558	1,81	30
79	96	CC/=C/O)C/C)/C)C)C/O)=O	12	315	Beta-oxidation	0,00004894	1,88	41
80	14	CC1/C=O)CC/N)CC/C)/CN)C1	2	93	Primarv hvdroxvl arouo oxidation	0,00004668	0,41	21
81	3	CC1(C O)CC( N)CC(C)( CN)C1	1	487	Methyl i:iroup oxidation	0,00004668	0,44	21
82	108	CCC/O)=O	14	319	Decarboxylation	0,00004254	0,58	100
83	15	CC1/C)CC/ N)CC/CN)/C=O)C1	2	93	Primarv hvdroxvl arouo oxidation	0,00002334	0,41	28
84	4	CC1(C)CC(N)CC(CN)(CO)C1	1	488	Methyl i:iroup oxidation	0,00002334	0,44	28
85	75	CC(C)(CC(C)(CO)C(O)=O)C=O	8	357	Oxidative deamination and N-dealkylation	0,00001591	0,35	5
86	69	CC(CC(O)=O){CC(C)(CN)C=O)C(O)=O	7	93	Primary hydroxvl arouo oxidation	0,00001296	-4,19	39
87	59	CC{CC(O)=O)(CC(C){CN)CO)C(O)=O	6	309	Ester hydrolvsis	0,00001296	-4,17	39
88	67	CC{Cl/CC/Cl/CO)C/O)=O)CO	7	487	Mettwl arouo oxidation	0,00001041	0,78	5
89	82	CC(CC(O)=O)(CC(C)(C=O)C(O)=O)C(O)=O	9	357	Oxidative deamination and N-dealkylation	0,000008098	-0,76	54
90	65	CC{C){C)CC{C){C{O)=O)C{O)=O	7	66	Aldehyde oxidation	0,000007558	1,48	27
91	72	CC(C){CC{CC{O)=O){CN)C{O)=O)C=O	7	93	Primary hydroxvl ciroup oxidation	0,000006481	-4,19	29
92	62	CC(C)(CC(CC(O)=O)(CN)C(O)=O)CO	6	309	Ester hydrolysis	0,000006481	-4,17	29
93	103	CC(CC(O)=O)C=C/C)C/O)=O	13	216	Decarboxylation	0,000004688	0,98	71
94	84	CC(C)(CC(CC(O)=O)(C=O)C(O)=O)C(O)=O	9	357	Oxidative deamination and N-dealkylation	0,000004049	-0,76	37
95	93	CC(C)(C)CC(C=O)C(0)=0	11	93	Primary hydroxvl ciroup oxidation	0,00000275	1,36	40
96	88	CC(C)(C)CC(CO)C(O)=O	10	216	Decarboxylation	0,00000275	1,38	40
97	78	CC(C)(C)CC(CO)(C=O)C(0)=0	8	357	Oxidative deamination and N-dealkylation	0,00000275	0,35	44
98	94	CC(C)(CC(CC(O)=O)C/O)=O)C(0)=0	11	216	Decarboxylation	0,000002699	0,28	29
99	92	CC(CC(O)=O)CC(C)(C(O)=O)C(O)=O	11	216	Decarboxylation	0,000002699	0,28	62
100	28	CC(C)(CC(C)(CC=O)CN)C(O)=O	3	37	Oxidative deamination and N-dealkylation	0,000002531	-2,37	10
101	27	CC(C)(CC=O)CC( C)(CN)C(0)=0	3	37	Oxidative deamination and N-dealkylation	0,000002531	-2,37	26
102	17	CC/C)/CC/C)/CC/N)O) CN)C/ 0)=0	2	309	Ester hvdrolvsis	0,000002531	-3,89	10
103	16	CC/C)/CC/N)O)CC/C)/CN)C/O)=O	2	309	Ester hvdrolvsis	0,000002531	-3,89	26
104	31	CC( C)( CC(=O) C(O)=O)CC( C)( O)CN	3	309	Ester hydrolysis	0,000001581	-0,96	24
105	30	CC( C)( O)CC( C)( CC(=O)C(O)=O)CN	3	309	Ester hydrolysis	0,000001581	-0,96	16
106	83	CC(C)(C)CC(CO)(C(O)=O)C(0)=0	9	66	Aldehyde oxidation	0,000000275	0,01	42
107	98	CC(0)(CC(0)=O)CC(C)(C(0)=O)C(O)=O	12	164	Beta-oxidation	2,699E-07	-1,22	60
108	95	CC(C)CC(CC(O)=O)(C(O)=O)C(O)=O	11	216	Decarboxylation	0,000000135	0,28	56
109	24	CC1(C)CC(=O)CC( C)(C(O)=O)C1	3	356	Oxidative deamination and N-dealkylation	2,5E-09	1,63	10
110	87	CC/CC/O)=O)/CC/C\/C/O\=O)C/O)=O)C/O)=O	10	66	Aldehvde Oxidation	8E-10	-0,50	51
111	89	CC(C)(CC(CC(O)=O)(C(O)=O)C(O)=O)C(O)=O	10	66	Aldehyde oxidation	4E-10	-0,50	34
112	39	CC1(C(O)=O)CC(=O)CC(C)(CN)C1	4	356	Oxidative deamination and N-dealkylation	3E-10	-3,04	22
113	40	CC1(C)CC(=O)CC(CN)(C(O)=O)C1	4	356	Oxidative deamination and N-dealkylation	1E-10	-3,04	33

 

 

Persistence (“P/vP”):

In order to assess the biodegradation potential of the relevant degradation products, the (Q)SAR models CATALOGIC 301 C v .09.13 was applied.    

- CATALOGIC 301 C v .09.13 (OASIS Catalogic v5.11.19) predicted for the substance 112 metabolites, identifying 40 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record). 4 of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD). The other 36 relevant metabolites were estimated to be not readily biodegradable.

In conclusion, the majority of the predicted metabolites present in a concentration of ≥ 0.1% are estimated to be not readily biodegradable and should be considered as potentially P/vP from a precautionary point of view.

 

Bioaccumulation (“B/vB”):

None of the relevant modelled degradation products of the substance were estimated to exhibit log Kow values of ≥ 4.5 (see Table 1), thus they do not fulfil the screening criteria for bioaccumulation (B/vB) as laid down in Section 3.1 of REACH Annex XIII.

Based on the estimation data available for the modelled metabolites, all (relevant) metabolites of the substance are concluded to be “not B” and “not vB”.

 

Toxicity (“T”):

As the predicted degradation products are not likely to fulfil both the P/vP and B/vB criteria, no information was collected on their toxicity properties.

 

Overall conclusion:

1. Sufficient test data are available to assess the PBT/vPvB properties of the substance.


2. Potentially relevant degradation products were modelled using (Q)SAR model CATALOGIC 301 C v .09.13 (OASIS Catalogic v5.11.19):

2a. Based on modelled data relevant degradation products present in concentration of ≥ 0.1% (parent) do neither fulfil the PBT criteria (not PBT) nor the vPvB criteria (not vPvB).

2b. However, 36 predicted relevant metabolites present in concentration of ≥0.1% should be considered as potentially P/vP from a precautionary point of view.

 

In conclusion, the substance and its relevant metabolites are not PBT/vPvB.