Physicochemical Properties
| Molecular Formula | C13H11N |
| Molecular Weight | 181.233143091202 |
| Exact Mass | 181.089 |
| Elemental Analysis | C, 86.15; H, 6.12; N, 7.73 |
| CAS # | 153-78-6 |
| Related CAS # | 2-Aminofluorene-13C;335081-08-8;2-Aminofluorene-d11;347841-44-5 |
| PubChem CID | 1539 |
| Appearance | Off-white to light yellow solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 379.3±21.0 °C at 760 mmHg |
| Melting Point | 124-128 °C(lit.) |
| Flash Point | 204.8±17.4 °C |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.697 |
| LogP | 2.88 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 14 |
| Complexity | 213 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | NC1=CC(CC2=C3C=CC=C2)=C3C=C1 |
| InChi Key | CFRFHWQYWJMEJN-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C13H11N/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7,14H2 |
| Chemical Name | 9H-fluoren-2-amine |
| Synonyms | 2-Aminofluorene, 2-Fluorenamine |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | 2-Aminofluorene (0-100 μM, 1-5 days) results in a dose-dependent inhibition of the immune response against LPS, DNP-Ficoll, and sheep erythrocytes (SRBC)[2]. 2. Lymphoproliferative responses to LPS and Con A are suppressed by aminofluorene (0-100 μM, 1-5 days, 3 days, spleen cells)[2]. |
| ln Vivo | In rapid acetylator mice (C57BL/6J), 2-Aminofluorene (60 mg/kg, ip) accumulates double the 2-Aminofluorene-DNA adducts of slow acetylators (A/J)[3]. 2-In acetylator congenic hamsters, 2-aminofluorene (60 mg/kg, ip) ip) generates significantly larger quantities of DNA adducts in tumor-target organs than in non-target organs[4]. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites N-HYDROXY METABOLITES ... /HAVE BEEN/ STRONGLY IMPLICATED AS PROXIMATE CARCINOGENIC DERIVATIVES OF AROMATIC AMINES & AMIDES. THUS, IN RAT & SOME OTHER SPECIES, N-HYDROXYAMIDES & THEIR CONJUGATES WERE DEMONSTRATED TO BE METABOLITES OF SOME AROMATIC AMINES & AMIDES, INCL 2-FLUORENAMINE ... THE ENZYME-CATALYZED ACETYLATION OF 3 CARCINOGENIC AROMATIC AMINES, 2-AMINOFLUORENE, 4-AMINOBIPHENYL, & 2-AMINONAPHTHALENE, HAS BEEN MEASURED IN LIVER CYTOSOL FROM VARIOUS SPECIES. DOG LIVER CYTOSOL CONTAINED NO DETECTABLE ACTIVITY. THE LIVER OF THIS SPECIES IS UNSUSCEPTIBLE TO CARCINOGENIC ACTION OF THESE CMPD. THIS IS INDIRECT EVIDENCE INDICATING THAT ACETYLATION IS IMPORTANT IN TOXICITY OF THESE CMPD. Activation of 2-AAF /2-acetylaminofluorene/ to N-hydroxy-2-aminofluorene, a potent mutagen to Salmonella strains, by guinea pig liver (S-9) mix afforded potent mutagen to Salmonella strains, by guinea pig 2-aminofluorene (AF) as well as N-OH-AAF /N-hydroxy-acetylaminofluorene/. Mutagenicities of 2-aminofluorene & N-hydroxy-2-aminofluorene were inhibited by antisera against NADPH-cytochrome C reductase & by paraoxon. While the mutagenic activity of 2-acetylaminofluorene to N-hydroxy-2-aminofluorene can be produced by N-hydroxylation of 2-aminofluorene or deacetylation of N-hydroxy-2-aminofluorene, the data suggested that deacetylation of 2-acetylaminofluorene (to 2-aminofluorene), followed by N-hydroxylation to produce N-hydroxy-2-aminofluorene, was the main pathway for the mutagenic activation of 2-acetylaminofluorene by guinea-pig liver (S-9) mix. 2-aminofluorene has known human metabolites that include 2-Acetylaminofluorene. |
| References |
[1]. Genetic toxicity of 2-acetylaminofluorene, 2-aminofluorene and some of their metabolites and model metabolites. Mutat Res. 1994 Oct;318(2):73-114. [2]. Immunosuppressive effects of 2-acetylaminofluorene and 2-aminofluorene on murine splenocytes culture. Drug Chem Toxicol. 1989 Sep-Dec;12(3-4):297-311. [3]. 2-Aminofluorene-DNA adduct formation in acetylator congenic mouse lines. Carcinogenesis. 1989 Apr;10(4):705-9. |
| Additional Infomation |
2-Aminofluorene can cause cancer according to an independent committee of scientific and health experts. 2-aminofluorene is a brown crystal powder. (NTP, 1992) Mechanism of Action CANCERS OF THE GI TRACT, ESP OF THE COLON, ARE PREVALENT IN INDUSTRIALIZED NATIONS. NUTRITIONAL FACTORS & THE INTESTINAL FLORA HAVE BEEN ASSIGNED CAUSAL ROLES IN THE ETIOLOGY OF THESE NEOPLASIAS. ANAEROBIC BACTERIA (BACTEROIDES FRAGILIS G4841, B VULGATUS K871, & B THETAIOTAOMICRON T2979, ISOLATES OF HUMAN ORIGIN) POSSESS ENZYMATIC ABILITY TO CONVERT 2-AMINOFLUORENE TO SUBSTANCES MUTAGENIC TO SALMONELLA TYPHIMURIUM. THE AMES ASSAY HAVE BEEN ADAPTED TO THE STUDY OF POSSIBLE FACTORS CONTRIBUTING TO GI CANCERS. CULTURES OF THE ANAEROBES WERE GROWN FOR 28 HR AT 37 °C, DISRUPTED BY SONICATION, CENTRIFUGED, & THE SUPERNATANT COLLECTED. ONE ML OF THE BACTERIAL EXTRACT WAS MIXED WITH EITHER 2-NITROFLUORENE OR 2-AMINOFLUORENE (FINAL CONCN 5 MG/ML) & INCUBATED AT 37 °C FOR 24 HR & ASSAYED FOR MUTAGENICITY USING TA1538. IT WAS FOUND THAT FILTRATES OF CULTURES OF B VULGATUS GROWN IN THE PRESENCE OF EITHER 2-NITROFLUORENE OR 2-AMINOFLUORENE WERE DEVOID OF SUBSTANCES POSSESSING DIRECT-ACTING FRAMESHIFT MUTAGENIC ACTIVITY; HOWEVER SUCH ACTIVITY WAS EVIDENT WHEN THE FILTRATES WERE INCUBATED IN THE PRESENCE OF MICROSOMAL ENZYMES. THE PRESENT FINDINGS INDICATE THAT THE CONVERSION OF 2-NITROFLUORENE TO 2-AMINOFLUORENE BY ANAEROBIC BACTERIA IS PROBABLY NOT THE COMPLETE EXPLANATION FOR REDUCTION IN YIELD OF MUTANTS OBSERVED IN OTHER AMES/GI TRACT SHORT-TERM ASSAYS USING GERM-FREE ANIMALS THAT WERE COLONIZED WITH SALMONELLA & B VULGATUS. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5179 mL | 27.5893 mL | 55.1785 mL | |
| 5 mM | 1.1036 mL | 5.5179 mL | 11.0357 mL | |
| 10 mM | 0.5518 mL | 2.7589 mL | 5.5179 mL |