Gramine

Modify Date: 2024-01-02 10:03:22

Gramine structure	Common Name	Gramine
	CAS Number	87-52-5	Molecular Weight	174.242
	Density	1.1±0.1 g/cm3	Boiling Point	293.9±15.0 °C at 760 mmHg
	Molecular Formula	C₁₁H₁₄N₂	Melting Point	132-134 °C(lit.)
	MSDS	Chinese USA	Flash Point	131.5±20.4 °C

Use of 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].

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

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.

Density	1.1±0.1 g/cm3
Boiling Point	293.9±15.0 °C at 760 mmHg
Melting Point	132-134 °C(lit.)
Molecular Formula	C₁₁H₁₄N₂
Molecular Weight	174.242
Flash Point	131.5±20.4 °C
Exact Mass	174.115692
PSA	19.03000
LogP	1.90
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.631
Storage condition	Refrigerator (+4°C)
Water Solubility	PRACTICALLY INSOLUBLE

Gramine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL7525000

CHEMICAL NAME :: Indole, 3-((dimethylamino)methyl)-

CAS REGISTRY NUMBER :: 87-52-5

LAST UPDATED :: 199712

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C11-H14-N2

MOLECULAR WEIGHT :: 174.27

WISWESSER LINE NOTATION :: T56 BMJ D1N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

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

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 122 mg/kg

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

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 46 mg/kg

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 **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 127 gm/kg/3W-C

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

Precursor 9
CAS#:120-72-9 Indole CAS#:50-00-0 Formaldehyde CAS#:124-40-3 Dimethylamine CAS#:30354-18-8 N,N-Dimethylmet...
CAS#:51-80-9 Bis(dimethylami... CAS#:27409-13-8 N,N-dimethyl-1H... CAS#:487-89-8 Indole-3-carbox... CAS#:62992-33-0 1-ethoxy-N,N-di...
CAS#:83-34-1 3-Methylindole
DownStream 10
CAS#:487-89-8 Indole-3-carbox... CAS#:4837-74-5 (4-Methoxy-1H-i... CAS#:19260-03-8 1H-indol-3-ylme... CAS#:83-34-1 3-Methylindole
CAS#:25796-04-7 4-Bromotryptophan CAS#:999-59-7 Methyl 3-(dimet... CAS#:832-97-3 DL-INDOLE-3-LAC... CAS#:80360-14-1 3-Iodo-1-(pheny...
CAS#:81630-83-3 2-(5-chloro-1H-... CAS#:87-51-4 3-Indoleacetic acid

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%

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol.

Proc. Natl. Acad. Sci. U. S. A. 112 , 8296-301, (2015)

Tramadol, previously only known as a synthetic analgesic, has now been found in the bark and wood of roots of the African medicinal tree Nauclea latifolia. At present, no direct evidence is available ...

NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides.

FEBS Lett. 374(3) , 387-92, (1995)

It is shown that NMR titrations can be used on a quantitative basis to derive binding constants and binding modes of ds-DNA ligand complexes from several signals. The results are partially at variance...

Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs.

Arch. Tierernahr. 55(1) , 1-16, (2001)

The effects of feeding varied levels of low- and high-gramine yellow lupin seeds (LG and HG, respectively), and of synthetic gramine added to the diets in amounts ranging from 0.15 to 1.2 g per kg wer...

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

BioBioPha
China
Product Name: Gramine
Price: ￥Inquiry/50mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Xueping-Zheng

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Gramine
Price: ￥128.0/20mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Gramine
Price: $280.0/20mg
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Gramine
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

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Gramine

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