Phenpromethamine

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;
	(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]

^ 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.

[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.

[Elks2014-2] 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.

[pmid18500382-3] 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.

[CohenTravis2021-4] 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.

[TsumuraKiguchi2019-5] 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.

[canadian_publication-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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