Deterenol

Deterenol
Clinical data
Trade names	Betafrine
Other names	Isopropylnorsynephrine, Isopropyloctopamine
Identifiers
	IUPAC name 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenol;
CAS Number	7376-66-1 ;
PubChem CID	23843;
ChemSpider	22290;
UNII	BR971OUC9M;
KEGG	D03700;
ChEMBL	ChEMBL109378;
CompTox Dashboard (EPA)	DTXSID90956502 ;
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)NCC(C1=CC=C(C=C1)O)O;
	InChI InChI=1S/C11H17NO2/c1-8(2)12-7-11(14)9-3-5-10(13)6-4-9/h3-6,8,11-14H,7H2,1-2H3; Key:MPCPSVWSWKWJLO-UHFFFAOYSA-N;

Deterenol (also known as Isopropylnorsynephrine and Isopropyloctopamine; trade name Betafrine) is a synthetic stimulant drug which acts as a beta agonist. It has been found as an ingredient of dietary supplement products, but is banned in most countries due to risk of cardiac arrest.[1][2][3][4][5]

References

Anderson WG (June 1983). "The sympathomimetic activity of N-isopropyloctopamine in vitro". The Journal of Pharmacology and Experimental Therapeutics. 225 (3): 553–8. PMID 6306210.
Mercader J, Wanecq E, Chen J, Carpéné C (September 2011). "Isopropylnorsynephrine is a stronger lipolytic agent in human adipocytes than synephrine and other amines present in Citrus aurantium". Journal of Physiology and Biochemistry. 67 (3): 443–52. doi:10.1007/s13105-011-0078-2. PMID 21336650. S2CID 22449550.
Venhuis B, Keizers P, van Riel A, de Kaste D (June 2014). "A cocktail of synthetic stimulants found in a dietary supplement associated with serious adverse events". Drug Testing and Analysis. 6 (6): 578–81. doi:10.1002/dta.1664. PMID 24802503.
Zhao J, Wang M, Avula B, Khan IA (March 2018). "Detection and quantification of phenethylamines in sports dietary supplements by NMR approach". Journal of Pharmaceutical and Biomedical Analysis. 151: 347–355. doi:10.1016/j.jpba.2018.01.025. PMID 29413984. S2CID 46837518.
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: 1–7. doi:10.1080/15563650.2021.1894333. PMID 33755516.

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[1] Anderson WG (June 1983). "The sympathomimetic activity of N-isopropyloctopamine in vitro". The Journal of Pharmacology and Experimental Therapeutics. 225 (3): 553–8. PMID 6306210.

[2] Mercader J, Wanecq E, Chen J, Carpéné C (September 2011). "Isopropylnorsynephrine is a stronger lipolytic agent in human adipocytes than synephrine and other amines present in Citrus aurantium". Journal of Physiology and Biochemistry. 67 (3): 443–52. doi:10.1007/s13105-011-0078-2. PMID 21336650. S2CID 22449550.

[3] Venhuis B, Keizers P, van Riel A, de Kaste D (June 2014). "A cocktail of synthetic stimulants found in a dietary supplement associated with serious adverse events". Drug Testing and Analysis. 6 (6): 578–81. doi:10.1002/dta.1664. PMID 24802503.

[4] Zhao J, Wang M, Avula B, Khan IA (March 2018). "Detection and quantification of phenethylamines in sports dietary supplements by NMR approach". Journal of Pharmaceutical and Biomedical Analysis. 151: 347–355. doi:10.1016/j.jpba.2018.01.025. PMID 29413984. S2CID 46837518.

[5] 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: 1–7. doi:10.1080/15563650.2021.1894333. PMID 33755516.

Deterenol

See also

References