Gramine (HCID 6890)

概要

Gramine is an aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. It has a role as an antiviral agent, an antibacterial agent, a serotonergic antagonist and a plant metabolite. It is an aminoalkylindole, an indole alkaloid and a tertiary amino compound. It is a conjugate base of a gramine(1+).

名称と識別子

優先名称: Gramine
IUPAC: 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
現地名: グラミン
英語名: Gramine
分子式: C11H14N2
分子量: 174.24

名称と別名

Gramine87-52-53-(Dimethylaminomethyl)indoleDonaxineDonaxinGramin1-(1H-indol-3-yl)-N,N-dimethylmethanamine1H-Indole-3-methanamine, N,N-dimethyl-beta-DimethylaminomethylindoleN,N-Dimethyl-1H-indole-3-methanamine3-(N,N-Dimethylaminomethyl)indole(1H-indol-3-ylmethyl)dimethylamine

名称をさらに表示

グラミンN,N-ジメチル-1H-インドール-3-イルメタンアミン3-[(ジメチルアミノ)メチル]-1H-インドール3-(ジメチルアミノメチル)-1H-インドールドナキシン3-ジメチルアミノメチルインドール3-ジメチルアミノメチル-1H-インドールN,N-ジメチル-1H-インドール-3-メタンアミンN,N-ジメチル-1H-インドール-3-(メタンアミン)3-(ジメチルアミノメチル)インドール[(1H-インドール-3-イル)メチル]ジメチルアミンDoranineNSC 16892GRAMINE(RG)Gramine >Gramine,>99%

3-[(Dimethylamino)methyl]indoleN,N-Dimethyl-1H-indole-3-methylamineFGQ8A78L14DTXSID3058955NSC-16892CHEBI:289483-((DIMETHYLAMINO)METHYL)INDOLE3-[Dimethylaminomethyl]indole

データベース識別子

CAS: 87-52-5
PubChem CID: 6890
DTXSID: DTXSID3058955
ChEMBL: CHEMBL254348
ChEBI: CHEBI:28948
UNII: FGQ8A78L14
EC Number: 201-749-8
Nikkaji: J10.618F

物性

構造計算による物性

XLogP: 1.8
極性表面積: 19 Å²
水素結合供与体数: 1
水素結合受容体数: 1
回転可能結合数: 2
重原子数: 13
形式電荷: 0
複雑度: 167

実験および物理化学的性質

Melting Point138 - 139 °C

Physical DescriptionSolid

Collision Cross Section · 2 件

138.42 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.9 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 132 · 132-134 °C (lit.)
沸点: 295.23 °C · 295.23°C (rough estimate)
比重(密度): 1.0715 · 1.0715 (rough estimate)
屈折率: 1.55 · 1.5500 (estimate)
闪点: 167 °C · 167 °C
貯蔵温度: Refrigerator (+4°C)
溶解性: almost transparency in Methanol
酸解離定数(Pka): 17 · 17.00±0.30(Predicted)
外見: 粉
色: ベージュ
水溶解度: 実質的に不溶
Merck: 14 · 14,4533
BRN: 140521 · 140521
InChI: 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
InChIKey: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
SMILES: CN(C)Cc1c[nH]c2ccccc12
LogP: 2.177 · 2.177 (est)
CAS データベース: 87 · 87-52-5(CAS DataBase Reference)
NISTの化学物質情報: 1 H-Indole-3-methanamine, · 1H-Indole-3-methanamine, N,N-dimethyl-(87-52-5)
EPAの化学物質情報: 1 H-Indole-3-methanamine, · 1H-Indole-3-methanamine, N,N-dimethyl- (87-52-5)

化学的性質 · 1 件

化学的特性3-(Dimethylaminomethyl)indole [87-52-5], gramine, C11H14N2, Mr 174.25, mp 138 – 139 ℃, forms colorless needles. The compound is soluble in ethanol, diethyl ether, and chloroform and insoluble in water. It can be synthesized from indole by the Mannich reaction with dimethyl-amine and formaldehyde. Gramine is used to synthesize D,L-tryptophan, the plant growth regulators indole-3-acetic acid and indole-3-butanoic acid as well as the intermediate tryptamine.

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H314 (93.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 32 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information1H-Indole-3-methanamine, N,N-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Corr. 1B (93.8%)

安全データ

wgk: 3
tsca: TSCA listed
rtecs: NL7525000
hs_code: 29339900
risk_code: 34
hazard_code: C
safety_code: 45-36/37/39-26
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 Oral
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

General Manufacturing Information1H-Indole-3-methanamine, N,N-dimethyl-: ACTIVE

応用分野 · 2 件

使用Reactant for preparation of:Dopamine D2 receptor antagonistsAnti-malarial drugs5-indolyl-Mannich basesProliferation inhibitorsInhibitors of human mast cell chymasePreparation of DL-tryptophanPotential detoxification inhibitors of the crucifer phytoalexin brassinin3-vinylindolesSerotonin 5-HT6 receptor ligand templatesSelective protein kinase c delta (PKCδ) down regulators

一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

調製方法 · 1 件

純化方法Crystallise gramine from diethyl ether, ethanol or acetone. It sublimes at 59o/0.001mm. The hydrochloride crystallises from EtOH/Et2O with m 190.5-191.0o(dec). [Culvenor et al. Aust J Chem 17 1301 1964, Beilstein 22 III/IV 4302, 22/10 V 25.]

上流・下流製品情報

上流原料

インドールジメチルアミン Methanamine, 1-ethoxy-N,N-dimethyl-Gramine, N-oxide N,N-dimethyl-1H-indole-3-carboxamide N-メチル-N-メチレンメタンアミニウム·クロリドインドール-3-カルボキシアルデヒド N,N,N',N'-テトラメチルジアミノメタンホルマリンウラシル

下流製品

DL-トリプトファン 3-インドールアセトニトリル Indol-1-ylmethyl-dimethyl-amine 3-インドールメタノール

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グラミン

基本情報

概要