Chemistry:Homarylamine
Homarylamine (INN),[1] also known as 3,4-methylenedioxy-N-methylphenethylamine (MDMPEA) or as METHYL-H, is a chemical compound of the phenethylamine and methylenedioxyphenethylamine (MDxx) family.[2] It is the N-methyl derivative of homopiperonylamine (methylenedioxyphenethylamine; MDPEA; H).[2] The drug was patented by Merck & Co. in 1956[3] and studied as an antitussive (cough suppressant) in 1961.[2][4] 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).[2] According to Shulgin, homarylamine has been reported to be active as an antitussive (cough suppressant) at a dose of 30 mg.[2] No central effects were described as this dose.[2] Shulgin tried this dose and experienced a little tightness of facial muscles, but no mental effects whatsoever.[2]
Chemistry
Reactions
A practical application of homarylamine is in the synthesis of Roemerin (de).[5]
Analogues
Analogues of homarylamine include homopiperonylamine (MDPEA), lobivine (MDDMPEA), lophophine (MMDPEA), MDA, MDMA, hydrastine, and hydrastinine, among others.[2]
See also
- Substituted methylenedioxyphenethylamine
References
- ↑ "International Non-Proprietary Names for Pharmaceutical Preparations". Chronicle of the World Health Organization 12 (3). 1958. https://www.who.int/medicines/publications/druginformation/innlists/PL06.pdf.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. "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."
- ↑ U.S. Patent 2,820,739
- ↑ "Experimental Investigation of Nine Antitussive Drugs". Journal of Pharmaceutical Sciences 50 (3): 216–221. March 1961. doi:10.1002/jps.2600500309. Bibcode: 1961JPhmS..50..216S.
- ↑ "The Synthesis of l-Roemerine 1". Journal of the American Chemical Society 66 (8): 1290–1292. August 1944. doi:10.1021/ja01236a024. Bibcode: 1944JAChS..66.1290M.
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