Phenpromethamine

Sympathomimetic nasal decongestant (Phenethylamine group)
  • none
Legal statusLegal status
  • DE: Anlage I (Authorized scientific use only)
Identifiers
  • N-methyl-2-phenylpropan-1-amine
CAS Number
  • 93-88-9
PubChem CID
  • 22276
ChemSpider
  • 21277725
UNII
  • 7D4542I59V
ECHA InfoCard100.257.912 Edit this at WikidataChemical and physical dataFormulaC10H15NMolar mass149.237 g·mol−13D model (JSmol)
  • Interactive image
  • CC(CNC)C1=CC=CC=C1
InChI
  • 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 name Vonedrine), also known as N,β-dimethylphenethylamine, 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]

See also

References

  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. 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. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ "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.
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AdamantanesAdenosine antagonistsAlkylaminesAmpakinesArylcyclohexylaminesBenzazepinesCathinonesCholinergicsConvulsantsEugeroicsOxazolinesPhenethylamines
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DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
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See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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Phenethylamines


Stimulants: Phenylethanolamine

Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous


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