Gramine (Donaxine) is a naturally occurring indole alkaloid found in several plant species such as giant reed. Gramine is useful for the preparation of D2 receptor antagonists, proliferation inhibitors, DL-Tryptophan, 5-HT6 receptor ligand templates, and PKC down regulators.

Physicochemical Properties

Molecular Formula	C11H14N2
Molecular Weight	174.24
Exact Mass	174.115
CAS #	87-52-5
Related CAS #	87-52-5
PubChem CID	6890
Appearance	White to off-white solid powder
Density	1.1±0.1 g/cm3
Boiling Point	293.9±15.0 °C at 760 mmHg
Melting Point	132-134 °C(lit.)
Flash Point	131.5±20.4 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.631
LogP	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Heavy Atom Count	13
Complexity	168
Defined Atom Stereocenter Count	0
InChi Key	OCDGBSUVYYVKQZ-UHFFFAOYSA-N
InChi Code	InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
Chemical Name	3-(Dimethylaminomethyl)indole
Synonyms	NSC 16892; NSC-16892;Donaxine; Gramine; NSC16892
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	Gramine is an active agonist of the adiponectin receptor (AdipoR), having IC50 values of 3.2 μM for AdipoR2 and 4.2 μM for AdipoR1, respectively [1]. Potential β2-AR agonistic agent is gramine [2]. With IC50 values of 9.6±0.9 and 0.1±0.1 μM, respectively, gramme (20 μM to 1.2 nM) dose-dependently suppresses the development of AdipoR1/adipoR2-activated liver cancer lines (MCF-7 cells) [1].
References	[1]. Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay. PLoS One. 2013 May 14;8(5):e63354. [2]. 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.
Additional Infomation	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+). Gramine has been reported in Hordeum vulgare, Pinus hartwegii, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO:35 mg/mL (200.8 mM) Water:<1 mg/mL Ethanol:35 mg/mL (200.8 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (11.94 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (11.94 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (11.94 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.7392 mL	28.6961 mL	57.3921 mL
	5 mM	1.1478 mL	5.7392 mL	11.4784 mL
	10 mM	0.5739 mL	2.8696 mL	5.7392 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.