CAS 87-52-5|Gramine

Introduction:Basic information about CAS 87-52-5|Gramine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameGramine
CAS Number87-52-5Molecular Weight174.242
Density1.1±0.1 g/cm3Boiling Point293.9±15.0 °C at 760 mmHg
Molecular FormulaC11H14N2Melting Point132-134 °C(lit.)
MSDSChineseUSAFlash Point131.5±20.4 °C

Names

Name1-(1H-indol-3-yl)-N,N-dimethylmethanamine
SynonymMore Synonyms

Gramine BiologicalActivity

DescriptionGramine (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 CatalogSignaling Pathways >>GPCR/G Protein >>Adiponectin ReceptorSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>CancerResearch Areas >>InfectionResearch Areas >>Metabolic DiseaseNatural Products >>Alkaloid
Target

IC50: 3.2 µM (AdipoR2), 4.2 µM (AdipoR1)[1]

In VitroGramine 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.

Chemical & Physical Properties

Density1.1±0.1 g/cm3
Boiling Point293.9±15.0 °C at 760 mmHg
Melting Point132-134 °C(lit.)
Molecular FormulaC11H14N2
Molecular Weight174.242
Flash Point131.5±20.4 °C
Exact Mass174.115692
PSA19.03000
LogP1.90
Vapour Pressure0.0±0.6 mmHg at 25°C
Index of Refraction1.631
InChIKeyOCDGBSUVYYVKQZ-UHFFFAOYSA-N
SMILESCN(C)Cc1c[nH]c2ccccc12
Storage conditionRefrigerator (+4°C)
Water SolubilityPRACTICALLY INSOLUBLE

Toxicological Information

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

Safety Information

Hazard CodesXi:Irritant;
Risk PhrasesR36
Safety PhrasesS45-S36/37/39-S26
RIDADRNONH for all modes of transport
WGK Germany3
RTECSNL7525000
HS Code2933990090

Customs

HS Code2933990090
Summary2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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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
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