Homarylamine

Homarylamine
Clinical data
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
Legal status
Legal status	US: Schedule I (as a positional isomer of MDA);
Identifiers
	IUPAC name 2-(1,3-benzodioxol-5-yl)-N-methylethanamine;
CAS Number	451-77-4;
PubChem CID	10776;
ChemSpider	10321;
UNII	6FJ4B5B368;
ChEMBL	ChEMBL2104353;
CompTox Dashboard (EPA)	DTXSID90196385 ;
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNCCC1=CC2=C(C=C1)OCO2;
	InChI InChI=1S/C10H13NO2/c1-11-5-4-8-2-3-9-10(6-8)13-7-12-9/h2-3,6,11H,4-5,7H2,1H3; Key:OPJOMVMFYOUDPK-UHFFFAOYSA-N;
	(verify)

Homarylamine (INNTooltip International Nonproprietary Name),^[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

Reaction of homarylamine with formaldehyde gives hydrastinine.

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]

References

^ "International Non-Proprietary Names for Pharmaceutical Preparations" (PDF). Chronicle of the World Health Organization. 12 (3). 1958.
^ ^a ^b ^c ^d ^e ^f ^g ^h 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.

External links

METHYL-MDPEA - Isomer Design

[1] "International Non-Proprietary Names for Pharmaceutical Preparations" (PDF). Chronicle of the World Health Organization. 12 (3). 1958.

[PiHKAL-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h 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."

[US2820739-3] U.S. patent 2,820,739

[StefkoDenzelHickey1961-4] 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.

[5] 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.

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