N-Hydroxy-3,4-methylenedioxyamphetamine

Base Information

• Chemical Name: N-Hydroxy-3,4-methylenedioxyamphetamine
• CAS No.: 74698-47-8
• Molecular Formula: C10H13 N O3
• Molecular Weight: 195.218
• Hs Code.: 2932999099
• European Community (EC) Number: 634-555-0
• UNII: SJE1T2B1A7
• DSSTox Substance ID: DTXSID30860972
• Nikkaji Number: J413.581D
• Wikipedia: 3,4-Methylenedioxy-N-hydroxyamphetamine
• Wikidata: Q4043402
• ChEMBL ID: CHEMBL127313
• Mol file: 74698-47-8.mol

Synonyms:N-hydroxy MDA;N-hydroxy methylenedioxyamphetamine;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane hydrochloride;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane, (+-)-isomer;N-hydroxy-3,4-methylenedioxyamphetamine;N-OH-MDA

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Chemical Property of N-Hydroxy-3,4-methylenedioxyamphetamine

Chemical Property:

• Vapor Pressure: 1.73E-05mmHg at 25°C
• Boiling Point: 349.7°C at 760 mmHg
• PKA: 13.76±0.50(Predicted)
• Flash Point: 165.3°C
• PSA: 50.72000
• Density: 1.246g/cm³
• LogP: 1.71600
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC2=C(C=C1)OCO2)NO
• Uses: A structural analog of 3,4-Methylenedioxy Methamphetamine (M303985) aka “ecstasy”. Hallucinogen; CNS stimulant. Controlled substance.

Technology Process of N-Hydroxy-3,4-methylenedioxyamphetamine

There total 3 articles about N-Hydroxy-3,4-methylenedioxyamphetamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5) → N-hydroxy-3,4-methylenedioxyamphetamine (74698-47-8)

Guidance literature:

With hydroxylamine; sodium cyanoborohydride;

Reference yield:

3,4-methylenedioxyamphetamine (4764-17-4) → 1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5) + α-methyldopamine (555-64-6,14513-20-3) + N-hydroxy-3,4-methylenedioxyamphetamine (74698-47-8)

Guidance literature:

With rabbit liver cytochrome P₄₅₀IIB₄; 1,2-dilauroylphosphatidylcholine; NADPH; NADPH-cytochrome P₄₅₀ reductase; ascorbic acid; In water; at 37 ℃; for 0.0833333h; Mechanism; other (methylenedioxy)phenyl compounds; also in the hydroxyl radical system (ferric chloride, EDTA, potassium phosphate buffer, pH 7.4); demethylenation reaction;

DOI:10.1021/jm00113a028

Reference yield:

benzo[1,3]dioxol-5-yl-acetone oxime (136056-99-0,52271-42-8) → N-hydroxy-3,4-methylenedioxyamphetamine (74698-47-8)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; for 72h; Ambient temperature;

DOI:10.1002/jps.2600690220

upstream raw materials:

3,4-methylenedioxyamphetamine

1-(1,3-benzodioxol-5-yl)-2-propanone

benzo[1,3]dioxol-5-yl-acetone oxime

Refernces

• 1、 Fukuto,Kumagai,Cho. "Determination of the mechanism of demethylenation of (methylenedioxy)phenyl compounds by cytochrome P450 using deuterium isotope effects". . p. 2871 - 2876. Retrieved 2007/10/02.
• 2、 Braun,Shulgin,Braun. "Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)". . p. 192 - 195. Retrieved 2007/10/02.