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Phenpromethamine

From Wikipedia, the free encyclopedia
Sympathomimetic nasal decongestant (Phenethylamine group)

Pharmaceutical compound
Phenpromethamine
Clinical data
Trade namesVonedrine
Other namesN,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 classNorepinephrine–dopamine releasing agent
ATC code
  • None
Legal status
Legal status
Identifiers
  • N-methyl-2-phenylpropan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.257.912Edit this at Wikidata
Chemical and physical data
FormulaC10H15N
Molar mass149.237 g·mol−1
3D model (JSmol)
  • CC(CNC)C1=CC=CC=C1
  • InChI=1S/C10H15N/c1-9(8-11-2)10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3
  • Key:AUFSOOYCQYDGES-UHFFFAOYSA-N
  (verify)

Phenpromethamine (former brand nameVonedrine), also known asN,β-dimethylphenethylamine (MPPA,BMMPEA,β-Me-NMPEA,β,N-MePEA), is asympathomimeticnasal decongestant of thephenethylamine group.[1][2][3][4] It was previously marketed as anasal inhaler from 1943 through 1960 but is no longer available.[4][3][5] The medication is astimulant and is banned by theWorld Anti-Doping Agency.[6][3] It has been detected indietary supplements starting in the 2010s.[5][4]

The drug is amonoamine releasing agent (MRA) similarly toβ-phenethylamine,amphetamine, and other phenethylamines.[7] It is theN-methylderivative ofβ-methylphenethylamine (BMPEA) and the β-methyl derivative ofN-methylphenethylamine (NMPEA).[7] Phenpromethamine is known to act as anorepinephrine–dopamine releasing agent (NDRA), withEC50Tooltip half-maximal effective concentration values of 154 nM fornorepinephrine and 574 nM fordopamine in rat brainsynaptosomes, whereasserotonin was not reported.[7]

See also

[edit]

References

[edit]
  1. ^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.Bibcode:1943JAChS..65..674W.doi:10.1021/ja01244a049.ISSN 0002-7863.
  2. ^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.
  3. ^abcDocherty 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.
  4. ^abcCohen 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.
  5. ^abTsumura 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.
  6. ^"The 2006 WADA Prohibited List: Summary of Revisions"(PDF).2006 Canadian Centre for Ethics in Sport Advisory Notice. Archived fromthe original(PDF) on 11 April 2007.
  7. ^abcSchindler 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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