CAS Number329-89-5
Synonyms6-Aminonikotinsaeureamid; 2-Amino-5-carbamoylpyridine; Nicotinamide,6-amino; 6-Aminopyridine-3-carboxamide; FDA 0121; 6-aminonicotinamid; 2-Aminopyridine-5-carboxamide; 6-aminonicotinic amide; 6-Aminonicotinic acid amide; Aminonicotinamide; EINECS 206-349-7; 6-Aminonicotinamide; 3-PYRIDINECARBOXAMIDE,6-AMINO; 6-amino-3-pyridinecarboxamide; 6-amino-nicotinamide; MFCD00006327
Molecular FormulaC6H7N3O
Molecular Weight137.14
Purity99%
Density1.3±0.1 g/cm3
Boiling Point381.6±27.0 °C at 760 mmHg
Melting Point245-248 °C (lit.)
Appearancepowder
EINECS206-349-7
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 329-89-5 |
| Catalog No. | 2A-9021322 |
| Chinese Name | 6-氨基烟酰胺 |
| Synonyms | 6-Aminonikotinsaeureamid; 2-Amino-5-carbamoylpyridine; Nicotinamide,6-amino; 6-Aminopyridine-3-carboxamide; FDA 0121; 6-aminonicotinamid; 2-Aminopyridine-5-carboxamide; 6-aminonicotinic amide; 6-Aminonicotinic acid amide; Aminonicotinamide; EINECS 206-349-7; 6-Aminonicotinamide; 3-PYRIDINECARBOXAMIDE,6-AMINO; 6-amino-3-pyridinecarboxamide; 6-amino-nicotinamide; MFCD00006327 |
| Molecular Formula | C6H7N3O |
| Molecular Weight | 137.14 |
| Purity | 99 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 381.6±27.0 °C at 760 mmHg |
| Melting Point | 245-248 °C (lit.) |
| Appearance | powder |
| Storage Condition | This product should be sealed and stored away from |
| Packaging | II |
| Application | 6-Aminonicotinamide, a potent nicotinamide antimetabolite, is a competitive inhibitor (Ki=0.46 μM) of the NADP+-dependent enzyme glucose-6-phosphate dehydrogenase (G6PD). 6-Aminonicotinamide interfere |
| EINECS | 206-349-7 |
| HTC | 2933399090 |
| PubChem ID | 24891142 |
| MDL Number | MFCD00006327 |
| SMILES | NC(=O)c1ccc(N)nc1 |
| InChI | 1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10) |
| InChI Key | ZLWYEPMDOUQDBW-UHFFFAOYSA-N |
| Beilstein/REAXYS | 116042 |
| NACRES Code | NA.22 |
| UNSPSC | 12352100 |
| Hazard Symbols | Transport |
| MSDS | msds/21322_1_329_89_5.pdf |
| Bioactivity | 6-Aminonicotinamide, a potent antimetabolite of nicotinamide, is competitive NADP+-dependent enzyme glucose-6-phosphate dehydrogenase (G6PD) inhibitor (Ki=0.46 μM). 6-Aminonicotinamide interferes with glycolysis, resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as Cisplatin, in killing cancer cells[1][2][3][4]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Others >> Others In Vitro 6-Aminonicotinamide (100 nM; 7 days) causes a significant decrease in the human AR+, hormone-sensitive prostate cancer cell lines LNCaP and LAPC4, as well as the CRPC-derivative C4-2 and 22Rv1 cell models. 6-Aminonicotinamide (100 nM ± 10 nM R1881 as indicated for 3 days) increases both basal- and R1881-mediated ROS levels, suggesting 6-Aminonicotinamide is blocking the cells' antioxidant defense. 6-Aminonicotinamide also increases ROS levels in C4-2 cells[3]. In Vivo 6-Aminonicotinamide (20 mg/kg; i.p.; thress times; days 1, 10 or 11, and 21) alone induces a small but significant tumor growth delay (4.3±0.8 days). Treatment with 6-Aminonicotinamide followed by radiation induces a tumor growth delay of 57.0±3.8 days in CD8F1 breast tumor model[4]. References [1]. Cheng J, et al. TRIM21 and PHLDA3 negatively regulate the crosstalk between the PI3K/AKT pathway and PPP metabolism. Nat Commun. 2020;11(1):1880. Published 2020 Apr 20. [2]. Almugadam SH, et al. Influence of 6-aminonicotinamide (6AN) on Leishmania promastigotes evaluated by metabolomics: Beyond the pentose phosphate pathway. Chem Biol Interact. 2018;294:167-177. [3]. Tsouko E, et al. Regulation of the pentose phosphate pathway by an androgen receptor-mTOR-mediated mechanism and its role in prostate cancer cell growth. Oncogenesis. 2014;3(5):e103. Published 2014 May 26. [4]. Koutcher JA, et al. Effect of 6-aminonicotinamide on the pentose phosphate pathway: 31P NMR and tumor growth delay studies. Magn Reson Med. 1996;36(6):887-892. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 381.6±27.0 °C at 760 mmHg Melting Point 245-248 °C(lit.) Molecular Formula C6H7N3O Molecular Weight 137.139 Flash Point 184.6±23.7 °C Exact Mass 137.058914 PSA 82.00000 LogP 0.41 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.644 InChIKey ZLWYEPMDOUQDBW-UHFFFAOYSA-N SMILES NC(=O)c1ccc(N)nc1 |
| Use of | 6-Aminonicotinamide, a potent antimetabolite of nicotinamide, is competitive NADP+-dependent enzyme glucose-6-phosphate dehydrogenase (G6PD) inhibitor (Ki=0.46 μM). 6-Aminonicotinamide interferes with glycolysis, resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as Cisplatin, in killing cancer cells[1][2][3][4]. Properties Articles31 Name 6-aminonicotinamide Synonym More Synonyms 6-Aminonicotinamide Biological Activity Description 6-Aminonicotinamide, a potent antimetabolite of nicotinamide, is competitive NADP+-dependent enzyme glucose-6-phosphate dehydrogenase (G6PD) inhibitor (Ki=0.46 μM). 6-Aminonicotinamide interferes with glycolysis, resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as Cisplatin, in killing cancer cells[1][2][3][4]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Others >> Others References [1]. Cheng J, et al. TRIM21 and PHLDA3 negatively regulate the crosstalk between the PI3K/AKT pathway and PPP metabolism. Nat Commun. 2020;11(1):1880. Published 2020 Apr 20. [2]. Almugadam SH, et al. Influence of 6-aminonicotinamide (6AN) on Leishmania promastigotes evaluated by metabolomics: Beyond the pentose phosphate pathway. Chem Biol Interact. 2018;294:167-177. [3]. Tsouko E, et al. Regulation of the pentose phosphate pathway by an androgen receptor-mTOR-mediated mechanism and its role in prostate cancer cell growth. Oncogenesis. 2014;3(5):e103. Published 2014 May 26. [4]. Koutcher JA, et al. Effect of 6-aminonicotinamide on the pentose phosphate pathway: 31P NMR and tumor growth delay studies. Magn Reson Med. 1996;36(6):887-892. Chemical & Physical Properties Molecular Formula C6H7N3O Exact Mass 137.058914 PSA 82.00000 Index of Refraction 1.644 InChIKey ZLWYEPMDOUQDBW-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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