Gramine

Category	Reverse Transcriptases (RTs)
CAS	87-52-5
Description	Gramine is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties.

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Product Information

Synonyms	Donaxine; Gramine; NSC 16892; NSC-16892; NSC16892.
IUPAC Name	1-(1H-indol-3-yl)-N,N-dimethylmethanamine
Molecular Weight	174.24
Molecular Formula	C11H14N2
Canonical SMILES	CN(C)CC1=CNC2=CC=CC=C21
InChI	InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
InChIKey	OCDGBSUVYYVKQZ-UHFFFAOYSA-N
Boiling Point	560.92°C.at760.00mmHg(est)
Melting Point	138-139 °C.
Flash Point	131.5±20.4 °C
Purity	97 % (HPLC).
Density	1.1±0.1 g/cm3
Solubility	Chloroform, ethanol
Appearance	Solid Powder
Storage	Store at +4 °C, in dark place.
Complexity	168
Exact Mass	174.115698455
Index Of Refraction	1.631
In Vitro	Gramine significantly inhibited phosphorylation and nuclear translocation of Smad2 and Smad4 by blocking activity of the TGFβ-RII, RI and activation of inhibitory Smad7. Gramine inhibited angiogenic markers such as MMP-2, MMP-9, HIF-1α, VEGF, and VEGF-R2 as well as increased TIMP-2 expression. Furthermore, gramine induced apoptosis in DMBA induced tumour bearing animals by up regulating the pro apoptotic proteins Bax, cytochrome C, apaf-1, caspase-9 caspase-3 and PARP.
In Vivo	Three doses, i.e. 0.1, 0.2, and 0.3 × the LD50 of gramine (i.e. 50 mg/kg, 100 mg/kg, and 150 mg/kg) were administered orally to either sex of Swiss albino mice for 48 h to study the genotoxic activity in micronucleus assay as well as chromosomal aberration. Gramine showed potent antioxidant activity in both the assay. Gramine at the given dose lacks mutagenicity as well as found to possess antimutagenic efficacy. Interestingly, S9 enzymes increase the antimutagenic activity in a dose-dependent manner. There was no significant increase in the frequency of micronucleated polychromatic erythrocytes (MNPCEs), as well as no significant difference in the percentage of chromosomal aberrations was observed between the gramine groups and the negative groups but percentage of polychromatic erythrocytes (PCEs) is found to be higher in all the gramine groups.
PSA	19.03000
Target	Adiponectin Receptor; Adrenergic Receptor; Reverse Transcriptase
Vapor Pressure	0.0±0.6 mmHg at 25°C
XLogP3-AA	1.8