Gramine

• CAS: 87-52-5
• Catalog Number: ACM87525
• Category: Inhibitors
• Molecular Weight: 174.24
• Molecular Formula: C11H14N2
• Description: Gramine (Donaxine) is a natural alkaloid isolated from giant reed, acts as an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 µM for AdipoR2 and AdipoR1, respectively. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties.
• Synonyms: N,N-Dimethyl-1H-indole-3-methylamine
• IUPAC Name: 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
• 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
• InChI Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
• Boiling Point: 295.23 °C
• Melting Point: 132-134 °C
• Flash Point: 167 °C
• Density: 1.0715 g/cm³
• Solubility: Practically insoluble in water
• Appearance: Beige powder
• Storage: 4 °C
• Complexity: 168
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 174.115698455
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• Monoisotopic Mass: 174.115698455
• Physical State: Powder
• pKa: 17.00±0.30(Predicted)
• Refractive Index: 1.5500
• Rotatable Bond Count: 2
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsGramineaeArundo donax Linn.
• Topological Polar Surface Area: 19 Ų

Custom Q&A

What is the chemical formula for Gramine?

The chemical formula for Gramine is C11H14N2.

What is the molar mass of Gramine?

The molar mass of Gramine is 174.24 g/mol.

What is the melting point of Gramine?

The melting point of Gramine is 132-134 °C.

What color is Gramine in its powder form?

Gramine appears as a beige powder.

In which solvents is Gramine soluble?

Gramine is soluble in ethanol, diethyl ether, and chloroform.

What is one of the safety hazards associated with Gramine?

Gramine is classified with hazard code C and has risk statement 34.

How is Gramine synthesized?

Gramine is synthesized from indole by the Mannich reaction with dimethyl-amine and formaldehyde.

What are some of the uses of Gramine?

Gramine is used as a reactant for the preparation of various compounds like dopamine D2 receptor antagonists and proliferation inhibitors.

What role does ChEBI assign to Gramine?

ChEBI assigns the role of a plant metabolite, serotonergic antagonist, antiviral agent, and antibacterial agent to Gramine.

How is Gramine typically stored?

Gramine is typically stored at room temperature.

Synthetic Use

Downstream Synthesis Route 1

• 87-52-5

• 87-51-4
• 879-37-8

Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 409,410, 411[2] Chem. Zentralbl., 1956, vol. 127, p. 13930
[3] Journal of the American Chemical Society, 1948, vol. 70, p. 3770

Downstream Synthesis Route 2

• 87-52-5

• 192189-07-4

Reference: [1] Organic letters, 2002, vol. 4, # 5, p. 815 - 817

Downstream Synthesis Route 3

• 110-89-4
• 87-52-5

• 5355-42-0

Reference: [1]Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, Tong-Hua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun
[Journal of Asian Natural Products Research, 2017, vol. 19, # 6, p. 610 - 622]
[2]Howe et al.
[Journal of the American Chemical Society, 1945, vol. 67, p. 38]

Downstream Synthesis Route 4

• 120-72-9
• 87-52-5

• 1968-05-4

Reference: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1956,vol. 304,p. 26,30

Downstream Synthesis Route 5

• 87-52-5
• 77-78-1

• 19260-03-8

Reference: [1]Current Patent Assignee: ACOUSIA THERAPEUTICS - EP2871181, 2015, A1
Location in patent: Paragraph 0058

* For details of the synthesis route, please refer to the original source to ensure accuracy.