Chemistry:Phenpromethamine
Phenpromethamine (former brand name Vonedrine), also known as N,β-dimethylphenethylamine (MPPA, BMMPEA, β-Me-NMPEA, β,N-MePEA), is a sympathomimetic nasal decongestant of the phenethylamine group.[1][2][3][4] It was previously marketed as a nasal inhaler from 1943 through 1960 but is no longer available.[4][3][5] The medication is a stimulant and is banned by the World Anti-Doping Agency.[6][3] It has been detected in dietary supplements starting in the 2010s.[5][4]
The drug is a monoamine releasing agent (MRA) similarly to β-phenethylamine, amphetamine, and other phenethylamines.[7] It is the N-methyl derivative of β-methylphenethylamine (BMPEA) and the β-methyl derivative of N-methylphenethylamine (NMPEA).[7] Phenpromethamine is known to act as a norepinephrine–dopamine releasing agent (NDRA), with EC50 values of 154 nM for norepinephrine and 574 nM for dopamine in rat brain synaptosomes, whereas serotonin was not reported.[7]
See also
- β,N,N-Trimethylphenethylamine
- Methamphetamine (α-methylphenethylamine)
- Phenacylamine (β-ketophenethylamine)
- Phenylethanolamine (β-hydroxyphenethylamine)
- β-Methylamphetamine
References
- ↑ "The Condensation of Unsaturated Amines with Aromatic Compounds. The Preparation of β-Substituted Phenethylamines". Journal of the American Chemical Society 65 (4): 674–677. 1943. doi:10.1021/ja01244a049. ISSN 0002-7863. Bibcode: 1943JAChS..65..674W.
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 971–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA971.
- ↑ 3.0 3.1 3.2 "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". British Journal of Pharmacology 154 (3): 606–22. June 2008. doi:10.1038/bjp.2008.124. PMID 18500382.
- ↑ 4.0 4.1 4.2 "Nine prohibited stimulants found in sports and weight loss supplements: deterenol, phenpromethamine (Vonedrine), oxilofrine, octodrine, beta-methylphenylethylamine (BMPEA), 1,3-dimethylamylamine (1,3-DMAA), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylbutylamine (1,3-DMBA) and higenamine". Clinical Toxicology 59 (11): 975–981. March 2021. doi:10.1080/15563650.2021.1894333. PMID 33755516.
- ↑ 5.0 5.1 "A novel method to distinguish β-methylphenylethylamines from isomeric α-methylphenylethylamines by liquid chromatography coupled to electrospray ionization mass spectrometry". Forensic Toxicology 38 (2): 465–474. 2019. doi:10.1007/s11419-019-00511-z. ISSN 1860-8965.
- ↑ "The 2006 WADA Prohibited List: Summary of Revisions". 2006 Canadian Centre for Ethics in Sport Advisory Notice. http://www.cces.ca/pdfs/CCES-ADV-2006ListUpdate-E.pdf.
- ↑ 7.0 7.1 7.2 "The Supplement Adulterant β-Methylphenethylamine Increases Blood Pressure by Acting at Peripheral Norepinephrine Transporters". J Pharmacol Exp Ther 369 (3): 328–336. June 2019. doi:10.1124/jpet.118.255976. PMID 30898867.
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