Homarylamine

Homarylamine (INN;[1] also known as 3,4-methylenedioxy-N-methylphenethylamine and MDMPEA) is an antitussive (anti-cough) drug[2] which was patented in 1956 by Merck & Co.,[3] but has never been used medically as such.

Homarylamine
Clinical data
Other names1,3-benzodioxolyl-N-methyl-5-ethanamine;
3,4-methylenedioxy-N-methyl-2-phenylethylamine;
Norlobivine
Routes of
administration		Various
Legal status
Legal status
  • US-SCHEDULE I DRUG as Positional isomer of MDA
Identifiers
IUPAC name
  • 2-(1,3-Benzodioxol-5-yl)-N-methylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13NO2
Molar mass179.219 g·mol−1
3D model (JSmol)
SMILES
  • CNCCC1=CC2=C(C=C1)OCO2
InChI
  • InChI=1S/C10H13NO2/c1-11-5-4-8-2-3-9-10(6-8)13-7-12-9/h2-3,6,11H,4-5,7H2,1H3
  • Key:OPJOMVMFYOUDPK-UHFFFAOYSA-N
  (verify)

Chemically it is a substituted phenethylamine. It is the N-methylated analog of methylenedioxyphenethylamine (MDPEA). It is a schedule I drug in the USA as a positional isomer of MDA.

Methylenedioxyphenethylamine (MDPEA) for comparison

Reactions

Reaction of homoarylamine with formaldehyde gives hydrastinine.

See also
  • Hydrastine, an alkaloid derivative of homarylamine

References
  1. "International Non-Proprietary Names for Pharmaceutical Preparations" (PDF). Chronicle of the World Health Organization. 12 (3). 1958.
  2. Stefko PL, Denzel J, Hickey I (March 1961). "Experimental Investigation of Nine Antitussive Drugs". Journal of Pharmaceutical Sciences. 50 (3): 216–221. doi:10.1002/jps.2600500309.
  3. U.S. Patent 2,820,739



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