Phenpromethamine

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]

Phenpromethamine

Clinical data
Trade names	Vonedrine
Other names	N,β-Dimethylphenethylamine; N,β-Dimethylbenzeneethanamine; Phenylpropylmethylamine
ATC code	none
Legal status
Legal status	DE: Anlage I (Authorized scientific use only)
Identifiers
IUPAC name N-methyl-2-phenylpropan-1-amine
CAS Number	93-88-9
PubChem CID	22276
ChemSpider	21277725
UNII	7D4542I59V
CompTox Dashboard (EPA)	DTXSID20861690
ECHA InfoCard	100.257.912
Chemical and physical data
Formula	C10H15N
Molar mass	149.237 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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
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See also

• β-Methylphenethylamine
• Methamphetamine
• N-Methylphenethylamine

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. 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. 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. 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.