109921-55-3

Basic information

• Product Name: N-Isopropyl-5-methoxytryptamine
• Synonyms: N-Isopropyl-5-methoxytryptamine;5-Methoxy-N-(1-Methylethyl)-1H-indole-3-ethanaMine;N-(2-(5-methoxy-1H-indol-3-yl)ethyl)propan-2-amine
• CAS NO: 109921-55-3
• Molecular Formula: C14H20N2O
• Molecular Weight: 232.32
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 109921-55-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 391.5 °C at 760 mmHg
• Flash Point: 190.6 °C
• Appearance: /
• Density: 1.068 g/cm³
• Vapor Pressure: 5.74E-06mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: N-Isopropyl-5-methoxytryptamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropyl-5-methoxytryptamine(109921-55-3)
• EPA Substance Registry System: N-Isopropyl-5-methoxytryptamine(109921-55-3)

Safety Data

• Hazardous Substances Data: 109921-55-3(Hazardous Substances Data)

Usage

Description

N-Isopropyl-5-methoxytryptamine, also known as M262470, is a metabolite of 5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) found in humans. It is a psychotomimetic tryptamine derivative, which means it has psychoactive properties that can induce effects similar to those of hallucinogenic substances.

Uses

Used in Pharmaceutical Research:
N-Isopropyl-5-methoxytryptamine is used as a research compound for understanding the effects and mechanisms of action of tryptamine derivatives, particularly in the context of their psychotomimetic properties. This knowledge can contribute to the development of new therapeutic approaches for various psychiatric and neurological disorders.
Used in Drug Metabolism Studies:
As a metabolite of 5-MeO-DIPT, N-Isopropyl-5-methoxytryptamine is used in drug metabolism studies to investigate the biotransformation processes of tryptamine derivatives in the human body. This can help researchers understand how these substances are metabolized and excreted, which is crucial for assessing their safety and potential side effects.
Used in Psychedelic Research:
N-Isopropyl-5-methoxytryptamine is used as a research tool in psychedelic research to explore the effects of tryptamine derivatives on human consciousness, perception, and cognition. This can provide insights into the underlying neurochemical mechanisms of psychedelic experiences and contribute to the development of novel treatments for mental health conditions, such as depression, anxiety, and post-traumatic stress disorder (PTSD).

InChI:InChI=1/C14H20N2O/c1-10(2)16-9-11(6-7-15)13-8-12(17-3)4-5-14(13)16/h4-5,8-10H,6-7,15H2,1-3H3

Upstream product

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 67-64-1 acetone 
• 92292-22-3 C₁₄H₁₈N₂O 
• 4021-34-5 5-Methoxy-N,N-diisopropyltryptamine 

Relevant articles and documents

Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes

In vitro quantitative studies of the oxidative metabolism of (5-methoxy-N,N-diisopropyltryptamine, 5-MeO-DIPT, Foxy) were performed using human liver microsomal fractions and recombinant CYP enzymes and synthetic 5-MeO-DIPT metabolites. 5-MeO-DIPT was mainly oxidized to O-demethylated (5-OH-DIPT) and N-deisopropylated (5-MeO-IPT) metabolites in pooled human liver microsomes. In kinetic studies, 5-MeO-DIPT O-demethylation showed monophasic kinetics, whereas its N-deisopropylation showed triphasic kinetics. Among six recombinant CYP enzymes (CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6 and CYP3A4) expressed in yeast or insect cells, only CYP2D6 exhibited 5-MeO-DIPT O-demethylase activity, while CYP1A2, CYP2C8, CYP2C9, CYP2C19 and CYP3A4 showed 5-MeO-DIPT N-deisopropylase activities. The apparent Km value of CYP2D6 was close to that for 5-MeO-DIPT O-demethylation, and the Km values of other CYP enzymes were similar to those of the low-Km (CYP2C19), intermediate-Km (CYP1A2, CYP2C8 and CYP3A4) and high-Km phases (CYP2C9), respectively, for N-deisopropylation in human liver microsomes. In inhibition studies, quinidine (1 μM), an inhibitor of CYP2D6, almost completely inhibited human liver microsomal 5-MeO-DIPT O-demethylation at a substrate concentration of 10 μM. Furafylline, a CYP1A2 inhibitor, quercetin, a CYP2C8 inhibitor, sulfaphenazole, a CYP2C9 inhibitor and ketoconazole, a CYP3A4 inihibitor (5 μM each) suppressed about 60%, 45%, 15% and 40%, respectively, of 5-MeO-DIPT N-deisopropylation at 50 μM substrate. In contrast, omeprazole (10 μM), a CYP2C19 inhibitor, suppressed only 10% of N-deisopropylation by human liver microsomes, whereas at the same concentration the inhibitor suppressed the reaction by recombinant CYP2C19 almost completely. These results indicate that CYP2D6 is the major 5-MeO-DIPT O-demethylase, and CYP1A2, CYP2C8 and CYP3A4 are the major 5-MeO-DIPT N-deisopropylase enzymes in the human liver.

Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

A structure-activity relationship study was conducted on a series of tetrahydro-β-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNFα production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity.