117652-28-5

Basic information

• Product Name: 4-hydroxy-3-methoxymethamphetamine
• Synonyms: 4-Hydroxy-3-methoxymethamphetamine; 2-Methoxy-4-(2-(methylamino)propyl)phenol; 4,3-Hmm; Phenol, 2-methoxy-4-(2-(methylamino)propyl)-
• CAS NO: 117652-28-5
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• Mol File: 117652-28-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 311.5°Cat760mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.044g/cm³
• Vapor Pressure: 0.000306mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: 4-hydroxy-3-methoxymethamphetamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-methoxymethamphetamine(117652-28-5)
• EPA Substance Registry System: 4-hydroxy-3-methoxymethamphetamine(117652-28-5)

Safety Data

• Hazardous Substances Data: 117652-28-5(Hazardous Substances Data)

Usage

General Description

4-hydroxy-3-methoxymethamphetamine, also known as HMMA, is a chemical compound that belongs to the amphetamine class of drugs. It is a metabolite of the recreational drug MDMA, or ecstasy. HMMA is formed in the body as a result of the metabolism of MDMA and has been found to be present in biological samples of individuals who have ingested MDMA. The chemical structure of HMMA includes a hydroxyl group and a methoxy group, which contribute to its pharmacological effects on the central nervous system. Research has shown that HMMA may contribute to the neurotoxicity and long-term effects associated with MDMA use.

InChI:InChI=1/C11H17NO2/c1-8(12-2)6-9-4-5-10(13)11(7-9)14-3/h4-5,7-8,12-13H,6H2,1-3H3

Upstream product

• 97-53-0 4-allylguaiacol 
• 2503-46-0 1-(4-hydroxy-3-methoxyphenyl)2-propanone 
• 593-51-1 methylamine hydrochloride 
• 408325-58-6 4-(2-bromo-propyl)-2-methoxy-phenol 
• 74-89-5 methylamine 

Downstream Products

• 853062-39-2 C₁₆H₂₅NO₄ 

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.