Homarylamine
Chemical compound
From Wikipedia, the free encyclopedia
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).
- US: Schedule I (as a positional isomer of MDA)
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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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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
Reaction of homarylamine with formaldehyde gives hydrastinine.[citation needed]
A practical application of homarylamine is in the synthesis of Roemerin.[5]
Analogues
Analogues of homarylamine include homopiperonylamine (MDPEA), lobivine (MDDMPEA), lophophine (MMDPEA), MDA, MDMA, hydrastine, and hydrastinine, among others.[2]