1-(2H-1,3-benzodioxol-5-yl)propan-2-amine

• ChemBase ID: 1300
• Molecular Formular: C10H13NO2
• Molecular Mass: 179.21572
• Monoisotopic Mass: 179.09462866
• SMILES: O1c2cc(CC(N)C)ccc2OC1
• Canonical SMILES: CC(Cc1ccc2c(c1)OCO2)N
• InChI: InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
• InChIKey: NGBBVGZWCFBOGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2H-1,3-benzodioxol-5-yl)propan-2-amine
• IUPAC Traditional name: 3,4-methylenedioxyamphetamine; @3,4-methylenedioxyamphetamine
• Synonyms: α-Methyl-1,3-benzodioxole-5-ethanamine; α-Methyl-3,4-(methylenedioxy)phenethylamine Hydrochloride; (R,S)-3,4-Methylenedioxyamphetamine Hydrochloride; 3,4-Methylenedioxyphenylisopropylamine Hydrochloride; 5-(2-Aminopropyl)-1,3-benzodioxole Hydrochloride; MDA; Tenamfetamine Hydrochloride; 3,4-Methylenedioxy Amphetamine Hydrochloride; 3,4-Methylenedioxyamphetamine

Database IDs

• CAS Number: 6292-91-7; 4764-17-4
• PubChem SID: 160964760; 46506100
• PubChem CID: 1614
• CHEMBL: 6731
• Chemspider ID: 1555
• DrugBank ID: DB01509
• Wikipedia Title: 3,4-Methylenedioxyamphetamine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.5914439
• LogD (pH = 7.4): -1.0455191
• Log P: 1.4274839
• Molar Refractivity: 49.4721 cm^3
• Polarizability: 19.761404 Å^3
• Polar Surface Area: 44.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.15
• LOG S: -1.8
• Solubility (Water): 2.83e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.64 [HANSCH,C & LEO,AJ (1985)]

Pharmacology Properties

• Admin Routes: Oral, Sublingual
• Excretion: Renal
• Half Life: unknown
• Metabolism: Hepatic, CYP extensively involved
• Legal Status: Class A (UK); S9 (Australia); Schedule I (US); Schedule III (Canada)

DETAILS

DrugBank - DB01509

• Drug Groups: illicit; experimental
• Description: An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]
• External Links: Wikipedia

Toronto Research Chemicals - M303965

A metabolite of MDMA. Entactogen; synthetic amphetamine derivative with stimulant and hallucinogenic properties.Controlled substance (hallucinogen).

REFERENCES

• Hardman, H.F., et al.: Toxicol. Appl. Pharmacol., 25, 299 (1973)
• Braun, U., et al.: J. Pharm. Sci., 69, 192 (1973)
• Michel, R.E., et al.: J. Neurosci. Methods, 50, 61 (1973)