232257-97-5

Basic information

• Product Name: HEPTADECANOIC ACID TRYPTAMIDE
• Synonyms: Margaric acid tryptamide, MAT, N-[2-(3-Indolyl)ethyl]heptadecanamide, N-Heptadecanoyltryptamine
• CAS NO: 232257-97-5
• Molecular Formula: C27H44N2O
• Molecular Weight: 412.658
• Mol File: 232257-97-5.mol

Chemical Properties

• Melting Point: 112-116 °C
• Boiling Point: 585.8°C at 760 mmHg
• Flash Point: 308.1°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 1.05E-13mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: HEPTADECANOIC ACID TRYPTAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTADECANOIC ACID TRYPTAMIDE(232257-97-5)
• EPA Substance Registry System: HEPTADECANOIC ACID TRYPTAMIDE(232257-97-5)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 232257-97-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H44N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20-27(30)28-22-24-29-23-21-25-18-16-17-19-26(25)29/h16-19,21,23H,2-15,20,22,24H2,1H3,(H,28,30)

Upstream product

• 61-54-1 tryptamine 
• 40480-10-2 heptadecanoyl chloride 

Relevant articles and documents

INDOLE DERIVATIVES FOR TREATING NEURODEGENERATIVE DISEASES

The invention relates to a compound of the following formula (I), or to a pharmaceutically acceptable salt thereof or to a stereoisomer or mixture of stereoisomers at any proportions, where: X1 is a CH2 or C═O group; X2 is a linear saturated or unsaturated carbohydrate chain with 8 to 24 carbon atoms; R1 is a hydrogen atom or an OH or (C1-C6)alkoxy group such as methoxy; and R2 is a CH3 or CH2OR3 group, with R3 being a hydrogen atom or a (C1-C6)alkyl, CO—(C1-C6)alkyl or NH—(C1-C6)alkyl group. The invention also relates to the use of said compound as a drug, in particular for treating neurodegenerative diseases, and to a method for preparing same.

Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons

N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structure-activity relationships study led us to precise the role of a nitrogen atom into the aliphatic chain conferring to the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest in neurodegenerative diseases such as Parkinson's disease.