87-52-5

87-52-5 structure

Name: Gramine
Chemical Name: 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
CAS Number: 87-52-5
Molecular Formula: C₁₁H₁₄N₂
Molecular Weight: 174.242
Catalog: Chemical reagent Deuterated reagent
Create Date: 2018-07-22 19:58:37
Modify Date: 2025-08-20 15:19:05
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].

Name	1-(1H-indol-3-yl)-N,N-dimethylmethanamine
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

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 Receptor Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Cancer Research Areas >> Infection Research Areas >> Metabolic Disease Natural 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.

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

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

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 **

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

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

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%