N-[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine

• ChemBase ID: 128371
• Molecular Formular: C10H13NO3
• Molecular Mass: 195.21512
• Monoisotopic Mass: 195.08954328
• SMILES: CC(Cc1cc2c(cc1)OCO2)NO
• Canonical SMILES: ONC(Cc1ccc2c(c1)OCO2)C
• InChI: InChI=1S/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
• InChIKey: FNDCTJYFKOQGTL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine
• IUPAC Traditional name: N-[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine
• Synonyms: (±)-N-Hydroxy MDA; (±)-N-Hydroxy-3,4-methylenedioxyamphetamine; N-Hydroxy-α-methyl-1,3-benzodioxole-5-ethanamine; (±)-N-Hydroxy-3,4-(methylenedioxy)amphetamine; 3,4-Methylenedioxy-N-hydroxyamphetamine; N-Hydroxy MDA; N-Hydroxy-3,4-methylenedioxy Amphetamine; Methylenedioxyhydroxyamphetamine; (±)-N-羟基-3,4-亚甲基双氧安非他命

Database IDs

• CAS Number: 114562-59-3; 74698-47-8
• MDL Number: MFCD00274047
• PubChem SID: 162222679
• PubChem CID: 98528
• Chemspider ID: 88979
• Wikipedia Title: Methylenedioxyhydroxyamphetamine

CALCULATED PROPERTIES

• Acid pKa: 15.642844
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.4711034
• LogD (pH = 7.4): 1.5352403
• Log P: 1.5361224
• Molar Refractivity: 61.7295 cm^3
• Polarizability: 20.395277 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Toronto Research Chemicals - H825505

A structural analog of 3,4-Methylenedioxy Methamphetamine (M303985) aka “ecstasy”. Hallucinogen; CNS stimulant. Controlled substance.

REFERENCES

• Quinteros-Munoz, D. et al.: Behav. Neurosci., 124, 662 (2010)
• Glennon, R.A. et al.: Pharmacol. Biochem. Behav., 33, 909 (2010)