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 Betaphrine) is a 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]

^ 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. 59 (11): 975–981. doi:10.1080/15563650.2021.1894333. PMID 33755516.

[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. 59 (11): 975–981. doi:10.1080/15563650.2021.1894333. PMID 33755516.

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