74698-47-8

Basic information

• Product Name: N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane
• Synonyms: N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane;5-[2-(Hydroxyamino)propyl]-1,3-benzodioxole;N-Hydroxy-1-[3,4-(methylenedioxy)phenyl]-2-propanamine;N-Hydroxy-α-methyl-1,3-benzodioxole-5-ethaneamine;MDOH;MethylenedioxyhydroxyaMphetaMine;3,4-Methylenedioxy-N-hydroxyaMphetaMine;N-Hydroxy-α-Methyl-1,3-benzodioxole-5-ethanaMine
• CAS NO: 74698-47-8
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• Product Categories: Amines;Aromatics;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74698-47-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 349.7°C at 760 mmHg
• Flash Point: 165.3°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.573
• PKA: 13.76±0.50(Predicted)
• CAS DataBase Reference: N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane(74698-47-8)
• EPA Substance Registry System: N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane(74698-47-8)

Safety Data

• Hazardous Substances Data: 74698-47-8(Hazardous Substances Data)

Usage

Description

N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane, also known as M303985, is a structural analog of 3,4-Methylenedioxy Methamphetamine (MDMA), commonly referred to as "ecstasy." It is a synthetic compound with hallucinogenic and central nervous system (CNS) stimulant properties. Due to its psychoactive effects, it is classified as a controlled substance.

Uses

Used in Pharmaceutical Research:
N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane is used as a research chemical for the development of new medications and therapies. Its structural similarity to MDMA allows scientists to study its effects on the human body and potentially develop treatments for various conditions.
Used in Forensic Science:
As a controlled substance, N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane is used in forensic science for the identification and analysis of drug-related evidence in criminal investigations.
Used in Psychotherapy Research:
Due to its psychoactive properties, N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane is also used in research exploring its potential applications in psychotherapy, particularly in the treatment of mental health disorders such as post-traumatic stress disorder (PTSD), anxiety, and depression. However, it is important to note that its use in this context is highly regulated and subject to strict ethical guidelines.
Used in Recreational Settings:
Although not a recommended or legal application, N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane may be used recreationally for its hallucinogenic and stimulant effects. However, this use is associated with significant health risks and legal consequences, and it is not endorsed or supported by any reputable source.

InChI:InChI=1/C10H13NO3/c1-7(11-12)4-8-2-3-9-10(5-8)14-6-13-9/h2-3,5,7,11-12H,4,6H2,1H3

Upstream product

• 4764-17-4 3,4-methylenedioxyamphetamine 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 136056-99-0 benzo[1,3]dioxol-5-yl-acetone oxime 

Relevant articles and documents

Gas chromatographic/mass spectrometric assay for profiling the enantiomers of 3,4-methylenedioxymethamphetamine and its chiral metabolites using positive chemical ionization ion trap mass spectrometry

A qualitative GC/MS profile was obtained and its mass spectrometric features characterized for the analysis of the enantiomers of (RS)-3,4-methylenedioxmethamphetamine (MDMA) and its metabolites (RS)-3,4- methylenedioxyamphetamine (MDA), (RS)-4-hydroxy-3-methoxymethamphetamine (HMMA) and (RS)-4- hydroxy-3-methoxyamphetamine (HMA). A chiral derivatization method was selected to obtain the diastereomers required for the separation of the respective enantiomers with a non-chiral GC stationary phase. The selected derivatization consisted of a reaction with N-heptafluorobutyryl-(S)-prolyl chloride combined with a consecutive reaction with N-methyl-N-trimethylsilyltrifluoracetamid, resulting in N-[heptafluorobutyryl-(S)-prolyl]-O-trimethylsilyl derivatives. Detection was carried out with electron ionization and positive chemical ionization (PCI) ion trap mass spectrometry. Mass spectra of the derivatives of reference standards of the compounds of interest obtained with PCI demonstrated that this method simultaneously induces proton and charge-transfer reactions in the ion trap. The advantage is that high mass information is provided while some fragmentation remains to elucidate structural details. Subsequently, in three urine samples obtained from different and unrelated MDMA intoxications the enantiomers of MDMA and MDA were identified. In some urine samples also HMMA and/or HMA were found. In addition to these compounds, an unexpected compound and/or additional chiral metabolite, N-hydroxy-(RS)-3,4-methylenedioxyamphetamine, was identified in two out of three urine samples. Preliminary results also indicated an enantioselective metabolism in the N-demethylation pathway for MDMA in humans.

Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)

The known central nervous system activity of 3,4-methylenedioxyphenylisopropylamine and its N-methyl homolog prompted the synthesis of a series of analogs with substituents on the nitrogen atom. Most of these analogs (R = alkyl, alkenyl, hydroxy, alkoxy, and alkoxyalkyl) were prepared by the reductive alkylation of 3,4-methylenedioxyphenylacetone with the appropriate amine and sodium cyanoborohydride. Hindered isomers were synthesized indirectly. Measurements of their pharmacological activity in several animal assays and in human subjects indicated that the central activity decreased with the increasing bulk of the N-substituent.