29095-44-1

Basic information

• Product Name: INDOLE-3-(N,N-DIMETHYL)GLYOXYLAMIDE
• Synonyms: n,n-dimethyl-indole-3-glyoxylamid;INDOLE-3-(N,N-DIMETHYL)GLYOXYLAMIDE;3-INDOLYLGLYOXYLDIMETHYLAMIDE;N,N-dimethyl-alpha-oxo-1H-indole-3-acetamide;N,N-Dimethyl-α-oxo-1H-indole-3-acetamide;n,n-dimethyl-alpha-oxo-1h-indole-3-acetamid
• CAS NO: 29095-44-1
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• EINECS: 249-429-7
• Mol File: 29095-44-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 399.6 °C at 760 mmHg
• Flash Point: 195.5 °C
• Appearance: /
• Density: 1.266 g/cm³
• CAS DataBase Reference: INDOLE-3-(N,N-DIMETHYL)GLYOXYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: INDOLE-3-(N,N-DIMETHYL)GLYOXYLAMIDE(29095-44-1)
• EPA Substance Registry System: INDOLE-3-(N,N-DIMETHYL)GLYOXYLAMIDE(29095-44-1)

Safety Data

• Hazardous Substances Data: 29095-44-1(Hazardous Substances Data)

Upstream product

• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 124-40-3 dimethyl amine 
• 506-59-2 N,N-dimethylammonium chloride 
• 120-72-9 indole 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 65991-91-5 2-(1H-imidazol-1-yl)acetamide 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 5135-83-1 1-(1-ethyl-indol-3-yl)-2-dimethylamino-ethanol 
• 42062-39-5 α-(Dimethylaminomethyl)-1-methylindole-3-methanol 
• 4335-93-7 3-(dimethylaminoethyl)-1-methoxyindole 
• 22120-32-7 2-(5-chloro-1H-indol-3-yl)-N, N-dimethylethanamine 
• 17274-65-6 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole 
• 61-50-7 N,N-dimethyltryptamine 
• 38662-19-0 1-Methylindol-3-glyoxyl-N,N-dimethylamid 
• 101586-48-5 (1-butyl-indol-3-yl)-glyoxylic acid dimethylamide 

Relevant articles and documents

Noncompetitive inhibition of indolethylamine-N-methyltransferase by N, N-dimethyltryptamine and N, N-dimethylaminopropyltryptamine

Indolethylamine-N-methyltransferase (INMT) is a Class 1 transmethylation enzyme known for its production of N,N-dimethyltryptamine (DMT), a hallucinogen with affinity for various serotonergic, adrenergic, histaminergic, dopaminergic, and sigma-1 receptors. DMT is produced via the action of INMT on the endogenous substrates tryptamine and S-adenosyl-l-methionine (SAM). The biological, biochemical, and selective small molecule regulation of INMT enzyme activity remain largely unknown. Kinetic mechanisms for inhibition of rabbit lung INMT (rabINMT) by the product, DMT, and by a new novel tryptamine derivative were determined. After Michaelis-Menten and Lineweaver-Burk analyses had been applied to study inhibition, DMT was found to be a mixed competitive and noncompetitive inhibitor when measured against tryptamine. The novel tryptamine derivative, N-[2-(1H-indol-3-yl)ethyl]-N′,N′-dimethylpropane-1,3-diamine (propyl dimethyl amino tryptamine or PDAT), was shown to inhibit rabINMT by a pure noncompetitive mechanism when measured against tryptamine with a Ki of 84 μM. No inhibition by PDAT was observed at 2 mM when it was tested against structurally similar Class 1 methyltransferases, such as human phenylethanolamine-N-methyltransferase (hPNMT) and human nicotinamide-N- methyltransferase (hNNMT), indicating selectivity for INMT. The demonstration of noncompetitive mechanisms for INMT inhibition implies the presence of an inhibitory allosteric site. In silico analyses using the computer modeling software Autodock and the rabINMT sequence threaded onto the human INMT (hINMT) structure (Protein Data Bank entry 2A14) identified an N-terminal helix-loop-helix non-active site binding region of the enzyme. The energies for binding of DMT and PDAT to this region of rabINMT, as determined by Autodock, were ～6.34 and ～7.58 kcal/mol, respectively. Assessment of the allosteric control of INMT may illuminate new biochemical pathway(s) underlying the biology of INMT.

Synthesis of deuterium labeled tryptamine derivatives

The synthesis of deuterium labeled tryptamine derivatives, [2-(1H-indol-3-yl)-[2H4]-ethyl]-dimethylamine (DMT), [2H10]-diethyl-[2-(1H-indol-3-yl)-ethyl]-amine (DET), [2-(1H-indol-3-yl)-ethyl]-[2H6]-dipropyl-amine (DPT) and [2H2]-alpha-methyltryptamine (AMT) is described. The isotopically labeled compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays.

Trifluoroacetylation of Methylated -Derivatives of Tryptamine and Serotonine by Different Reagents: Synthesis, Spectroscopic Characterizations, and Separations by Capillary-Gas-Chromatography

-