Phenpromethamine
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| Trade names | Vonedrine |
| Other names | N,β-Dimethylphenethylamine; β,N-Dimethylphenethylamine; N,β-Dimethylbenzeneethanamine; Phenylpropylmethylamine; N-Methyl-2-phenylpropan-1-amine; MPPA; BMMPEA; β-Me-NMPEA; β,N-MePEA |
| Routes of administration | Nasal inhaler |
| Drug class | Norepinephrine–dopamine releasing agent |
| ATC code |
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| ECHA InfoCard | 100.257.912 |
| Chemical and physical data | |
| Formula | C10H15N |
| Molar mass | 149.237 g·mol−1 |
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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
[edit]- β,N,N-Trimethylphenethylamine
- Methamphetamine (α-methylphenethylamine)
- Phenacylamine (β-ketophenethylamine)
- Phenylethanolamine (β-hydroxyphenethylamine)
- β-Methylamphetamine
References
[edit]- ^ Weston AW, Ruddy AW, Suter CM (1943). "The Condensation of Unsaturated Amines with Aromatic Compounds. The Preparation of β-Substituted Phenethylamines". Journal of the American Chemical Society. 65 (4): 674–677. doi:10.1021/ja01244a049. ISSN 0002-7863.
- ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 971–. ISBN 978-1-4757-2085-3.
- ^ a b c Docherty JR (June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". British Journal of Pharmacology. 154 (3): 606–22. doi:10.1038/bjp.2008.124. PMC 2439527. PMID 18500382.
- ^ a b c Cohen PA, Travis JC, Vanhee C, Ohana D, Venhuis BJ (March 2021). "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. doi:10.1080/15563650.2021.1894333. PMID 33755516. S2CID 232338883.
- ^ a b Tsumura Y, Kiguchi A, Komatsuzaki S, Ieuji K (2019). "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. doi:10.1007/s11419-019-00511-z. ISSN 1860-8965. S2CID 212828763.
- ^ "The 2006 WADA Prohibited List: Summary of Revisions" (PDF). 2006 Canadian Centre for Ethics in Sport Advisory Notice. Archived from the original (PDF) on 11 April 2007.
- ^ a b c Schindler CW, Thorndike EB, Rice KC, Partilla JS, Baumann MH (June 2019). "The Supplement Adulterant β-Methylphenethylamine Increases Blood Pressure by Acting at Peripheral Norepinephrine Transporters". J Pharmacol Exp Ther. 369 (3): 328–336. doi:10.1124/jpet.118.255976. PMC 6533570. PMID 30898867.
External links
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