CAS 87-52-5|Gramine
| Common Name | Gramine | ||
|---|---|---|---|
| CAS Number | 87-52-5 | Molecular Weight | 174.242 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 293.9±15.0 °C at 760 mmHg |
| Molecular Formula | C11H14N2 | Melting Point | 132-134 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 131.5±20.4 °C |
Names
| Name | 1-(1H-indol-3-yl)-N,N-dimethylmethanamine |
|---|---|
| Synonym | More Synonyms |
Gramine BiologicalActivity
| Description | Gramine (Donaxine) is a natural alkaloid isolated from giant reed[2], acts as an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 µM for AdipoR2 and AdipoR1, respectively[1]. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist[2]. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties[1]. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Adiponectin ReceptorSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>CancerResearch Areas >>InfectionResearch Areas >>Metabolic DiseaseNatural Products >>Alkaloid |
| Target | IC50: 3.2 µM (AdipoR2), 4.2 µM (AdipoR1)[1] |
| In Vitro | Gramine is an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 µM for AdipoR2 and AdipoR1, respectively[1]. Gramine is a potential β2-AR agonist[2]. Gramine (20 µM to 1.2 nM) dose-dependently inhibits the growth of AdipoR1/adipoR2-positive cancer cell lines (MDA-MB-231 and MCF-7 cells), with IC50s of 9.6±0.9 and 0.1±0.1 µM, respectively[1]. |
| References | [1]. Sun Y, et al. Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay. PLoS One. 2013 May 14;8(5):e63354. [2]. Chikazawa M, et al. Identification of Functional Food Factors as β2-Adrenergic Receptor Agonists and Their Potential Roles in Skeletal Muscle. J Nutr Sci Vitaminol (Tokyo). 2018;64(1):68-74. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 293.9±15.0 °C at 760 mmHg |
| Melting Point | 132-134 °C(lit.) |
| Molecular Formula | C11H14N2 |
| Molecular Weight | 174.242 |
| Flash Point | 131.5±20.4 °C |
| Exact Mass | 174.115692 |
| PSA | 19.03000 |
| LogP | 1.90 |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.631 |
| InChIKey | OCDGBSUVYYVKQZ-UHFFFAOYSA-N |
| SMILES | CN(C)Cc1c[nH]c2ccccc12 |
| Storage condition | Refrigerator (+4°C) |
| Water Solubility | PRACTICALLY INSOLUBLE |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 250 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,11,1953
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 122 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- PSYPAG Psychopharmacologia (Berlin). (Berlin, Ger.) V.1-46, 1959-76. For publisher information, see PSCHDL. Volume(issue)/page/year: 16,385,1970
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 46 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 105,130,1952 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - species unspecified
- DOSE/DURATION :
- 127 gm/kg/3W-C
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in both tubules and glomeruli Endocrine - changes in spleen weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
- REFERENCE :
- TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 18,125,1980
Safety Information
| Hazard Codes | Xi:Irritant; |
|---|---|
| Risk Phrases | R36 |
| Safety Phrases | S45-S36/37/39-S26 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | NL7525000 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles26
More Articles| A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol. Proc. Natl. Acad. Sci. U. S. A. 112 , 8296-301, (2015) Tramadol, previously only known as a synthetic analgesic, has now been found in the bark and wood of roots of the African medicinal tree Nauclea latifolia. At present, no direct evidence is available ... | |
| NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides. FEBS Lett. 374(3) , 387-92, (1995) It is shown that NMR titrations can be used on a quantitative basis to derive binding constants and binding modes of ds-DNA ligand complexes from several signals. The results are partially at variance... | |
| Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs. Arch. Tierernahr. 55(1) , 1-16, (2001) The effects of feeding varied levels of low- and high-gramine yellow lupin seeds (LG and HG, respectively), and of synthetic gramine added to the diets in amounts ranging from 0.15 to 1.2 g per kg wer... |
Synonyms
| 1H-Indole-3-methanamine, N,N-dimethyl- |
| Gramin |
| Donaxine |
| Indole, 3-[(dimethylamino)methyl]- |
| Indole,3-[(dimethylamino)methyl] |
| Gramine |
| MFCD00005629 |
| 3-(Dimethylaminomethyl)indole |
| Indol-3-ylmethyldimethylamine |
| EINECS 201-749-8 |
| Donaxin |
| N,N-dimethyl-1H-indole-3-methanamine |
| 3-(N,N-dimethylaminomethyl) indole |
| N-(1H-indol-3-ylmethyl)-N,N-dimethylamine |
| 1H-Indole-3-methanamine,N,N-dimethyl |
| 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine |
| 3-[(Dimethylamino)methyl]indole |
| (indol-3-ylmethyl)dimethylamine |
