Methylenedioxymethylphenethylamine
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Homarylamine (
INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway. Before the advent of motorized transportation, they also provided accomm ...
; also known as 3,4-methylenedioxy-''N''-methylphenethylamine and MDMPEA) is an
antitussive Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including ana ...
(anti-cough) drug which was patented in 1956 by Merck & Co., but has never been used medically as such. Chemically it is a
substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...
. It is the '' N''-
methylated Methylation, in the chemical sciences, is the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These term ...
analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...
of
methylenedioxyphenethylamine 3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to 3,4-Methylenedioxyamphetamine, MD ...
(MDPEA). It is a schedule I drug in the USA as a positional isomer of MDA.


Reactions

Reaction of homoarylamine with
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
gives
hydrastinine Hydrastinine is a semisynthetic tetrahydroisoquinoline alkaloid made via the nitric acid induced hydrolysis of the alkaloid hydrastine hydrochloride, which is extracted from ''Hydrastis canadensis'' L. (Ranunculaceae). The drug was patented by B ...
.


See also

* Lobivine (MDDMPEA) *
Hydrastine Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900's. It is present in ...
, an alkaloid derivative of homarylamine


References

Methylenedioxyphenethylamines {{respiratory-system-drug-stub