Gramine

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].

Solid

Gramine is an aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. It has a role as a plant metabolite, a serotonergic antagonist, an antiviral agent and an antibacterial agent. It is an aminoalkylindole, an indole alkaloid and a tertiary amino compound. It is a conjugate base of a gramine(1+).

Derived from the condensation of indole with formaldehyde and dimethylamine. Cool dimethylamine to -5°C and add it to glacial acetic acid. Under the condition that the temperature does not exceed 5°C, add formaldehyde and indole, react at 30-40°C for 8 hours, cool to 5°C, adjust the pH to 1 with 40% sodium hydroxide, and cool the crystals of luzhuine. After filtering, washing with water, draining the crude product, heating and dissolving with acetone, cooling, precipitation of crystals, filtering and drying to obtain the finished product.

For the preparation of dopamine D2 receptor antagonists, antimalarial drugs, 5-indolyl-Mannich bases, proliferation inhibitors, human mast cell chymase inhibitors, DL-tryptophan, potentially cruciferous Plant antitoxin brassinolide detoxification inhibitor, 3-vinylindole, serotonin 5-HT6 receptor ligand template, selective protein kinase Cδ (PKCδ) negative regulator

Molecular Weight:174.24
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:174.115698455
Monoisotopic Mass:174.115698455
Topological Polar Surface Area:19
Heavy Atom Count:13
Complexity:168
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes