Homarylamine (), also known as 3,4-methylenedioxy-N-methylphenethylamine (MDMPEA) or as METHYL-H, is a chemical compound of the phenethylamine and methylenedioxyphenethylamine (MDxx) family. It is the N-methyl derivative of homopiperonylamine (methylenedioxyphenethylamine; MDPEA; H). The drug was patented by Merck & Co. in 1956 and studied as an antitussive (cough suppressant) in 1961. It is a schedule I drug in the United States as a positional isomer of 3,4-methylenedioxyamphetamine (MDA).

Use and effects Homarylamine was briefly mentioned by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved). According to Shulgin, homarylamine has been reported to be active as an antitussive (cough suppressant) at a dose of 30mg. No central effects were described as this dose. Shulgin tried this dose and experienced a little tightness of facial muscles, but no mental effects whatsoever.

Chemistry Reactions Reaction of homarylamine with formaldehyde gives hydrastinine.

A practical application of homarylamine is in the synthesis of .

Analogues Analogues of homarylamine include homopiperonylamine (MDPEA), lobivine (MDDMPEA), lophophine (MMDPEA), MDA, MDMA, hydrastine, and hydrastinine, among others. "There is a family of compounds, to be discussed elsewhere, that is called the Muni-Metro (see under METHYL-J). The simplest member is this compound, MDPEA, and under its chemically acceptable synonym, homopiperonylamine, it can be called “H”. Following that code, then, the N-methyl homologue of MDPEA is METHYL-H, and it has been looked at, clinically, as an antitussive agent. N-METHYL-MDPEA, or METHYL-H, or N-methyl-3,4-methylenedioxyphenethylamine is effective in this role at dosages of about 30 milligrams, but I have read nothing that would suggest that there were any central effects. I have tried it at this level and have found a little tightness of the facial muscles, but there was nothing at all in the mental area."

See also Substituted methylenedioxyphenethylamine

References

External links METHYL-MDPEA - Isomer Design