Homarylamine
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| Other names | MDMPEA; 1,3-Benzodioxolyl-N-methyl-5-ethanamine; 3,4-Methylenedioxy-N-methyl-2-phenylethylamine; Norlobivine; METHYL-H; METHYL-MDPEA; N-Me-MDPEA |
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| Formula | C10H13NO2 |
| Molar mass | 179.219 g·mol−1 |
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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
[edit]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
[edit]Reactions
[edit]Reaction of homarylamine with formaldehyde gives hydrastinine.[citation needed]
A practical application of homarylamine is in the synthesis of Roemerin.[5]
Analogues
[edit]Analogues of homarylamine include homopiperonylamine (MDPEA), lobivine (MDDMPEA), lophophine (MMDPEA), MDA, MDMA, hydrastine, and hydrastinine, among others.[2]
See also
[edit]References
[edit]- ↑ "International Non-Proprietary Names for Pharmaceutical Preparations" (PDF). Chronicle of the World Health Organization. 12 (3). 1958.
- 1 2 3 4 5 6 7 8 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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
- ↑ 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.
- ↑ 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.