Homarylamine

Homarylamine

Clinical data
Other names	1,3-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	451-77-4
PubChem CID	10776
ChemSpider	10321
UNII	6FJ4B5B368
ChEMBL	ChEMBL2104353
CompTox Dashboard (EPA)	DTXSID90196385
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol^−1
3D model (JSmol)	Interactive image
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
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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.

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.

A practical application of homarylamine is in the synthesis of Roemerin [de].^[4]

See also

• Lobivine (MDDMPEA)
• 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. Bibcode:1961JPhmS..50..216S. doi:10.1002/jps.2600500309.
3. U.S. patent 2,820,739
4. Marion, L., Grassie, V. (August 1944). "The Synthesis of l-Roemerine 1". Journal of the American Chemical Society. 66 (8): 1290–1292. Bibcode:1944JAChS..66.1290M. doi:10.1021/ja01236a024.