Norfenefrine Explained

Verifiedfields:	changed
Verifiedrevid:	462263073
Alt2:	Ball-and-stick model of (R)-Norfenefrine
Legal Status:	Rx-only
Metabolism:	m-Hydroxymandelic acid^[1] ^[2]
Cas Number:	536-21-0
Cas Supplemental:	15308-34-6 (hydrochloride)
Atc Prefix:	C01
Atc Suffix:	CA05
Pubchem:	4538
Chemspiderid:	4379
Unii:	D2P3M6SRN5
Kegg:	D08286
Chembl:	358040
Synonyms:	Norfenephrine; Norphenephrine; Norphenylephrine; meta-Norsynephrine; meta-Octopamine; 3-Octopamine; Adrianol; 3,β-Dihydroxyphenethylamine; 3,β-Dihydroxy-β-phenylethylamine
Iupac Name:	3-(2-Amino-1-hydroxyethyl)phenol
C:	8
H:	11
N:	1
O:	2
Smiles:	OC(c1cc(O)ccc1)CN
Stdinchi:	1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2
Stdinchikey:	LRCXRAABFLIVAI-UHFFFAOYSA-N

Norfenefrine, also known as meta-octopamine or norphenylephrine and sold under the brand name Novadral among others, is a sympathomimetic medication which is used in the treatment of hypotension (low blood pressure).^{[3] [4] [5]} Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.^[6]

Medical uses

Norfenefrine is used in the treatment of hypotension (low blood pressure). It is said to be similarly effective or less effective than midodrine.^{[7] [8] [9]}

Pharmacology

Pharmacodynamics

Norfenefrine is described as an α-adrenergic receptor agonist and sympathomimetic agent. It is said to act predominantly as an α₁-adrenergic receptor agonist.^[10]

Chemistry

Norfenefrine, also known as 3,β-dihydroxyphenethylamine, is a substituted phenethylamine derivative. It is an analogue of norepinephrine (3,4,β-trihydroxyphenethylamine), of meta-tyramine (3-hydroxyphenethylamine), of phenylephrine ((R)-β,3-dihydroxy-N-methylphenethylamine), of etilefrine (3,β-dihydroxy-N-ethylphenethylamine), and of metaterol (3,β-dihydroxy-N-isopropylphenethylamine), as well as of metaraminol ((1R,2S)-3,β-dihydroxy-α-methylphenethylamine).

Norfenefrine is used medically as the hydrochloride salt.

The predicted log P of norfenefrine is -0.28 to -0.95.^{[11] [12] [13]}

Society and culture

Names

Norfenefrine is the generic name of the drug and its . Synonyms of norfenefrine include hydroxyphenylethanolamine, nor-phenylephrine, and m-norsynephrine, among others. Brand names of norfenefrine include Novadral, A.S. COR, Coritat, Energona, Hypolind, Norfenefrin Ziethen, and Norfenefrin-Ratiopharm, among others.

Availability

Norfenefrine is marketed in Europe, Japan, and Mexico.

Notes and References

1. Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ . The physiological disposition of p-octopamine in man . Naunyn-Schmiedeberg's Archives of Pharmacology . 283 . 1 . 93–106 . 1974 . 4277715 . 10.1007/bf00500148 . 35523412 .
2. D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, Leon A . Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages . Neuroscience Letters . 469 . 3 . 348–351 . January 2010 . 20026245 . 10.1016/j.neulet.2009.12.025 . 12797090 .
3. Book: Elks, J. . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer US . 2014 . 978-1-4757-2085-3 . 22 July 2024 . 61.
4. Book: Macdonald F . Dictionary of Pharmacological Agents . 24 April 2012 . 1997 . CRC Press . 978-0-412-46630-4 . 104 .
5. Book: Index Nominum 2000: International Drug Directory . 24 April 2012 . 2000 . Taylor & Francis . 978-3-88763-075-1 . 750 .
6. Danielson TJ, Boulton AA, Robertson HA . m-Octopamine, p-octopamine and phenylethanolamine in rat brain: a sensitive, specific assay and the effects of some drugs . Journal of Neurochemistry . 29 . 6 . 1131–1135 . December 1977 . 340613 . 10.1111/j.1471-4159.1977.tb06519.x . 26137006 .
7. McTavish D, Goa KL . Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders . Drugs . 38 . 5 . 757–777 . November 1989 . 2480881 . 10.2165/00003495-198938050-00004 .
8. McClellan KJ, Wiseman LR, Wilde MI . Midodrine. A review of its therapeutic use in the management of orthostatic hypotension . Drugs Aging . 12 . 1 . 76–86 . January 1998 . 9467688 . 10.2165/00002512-199812010-00007 .
9. Maule S, Papotti G, Naso D, Magnino C, Testa E, Veglio F . Orthostatic hypotension: evaluation and treatment . Cardiovasc Hematol Disord Drug Targets . 7 . 1 . 63–70 . March 2007 . 17346129 . 10.2174/187152907780059029 .
10. Docherty JR . Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA) . Br J Pharmacol . 154 . 3 . 606–622 . June 2008 . 18500382 . 2439527 . 10.1038/bjp.2008.124 .
11. Web site: Norfenefrine . PubChem . 31 August 2024.
12. Web site: Norfenefrine: Uses, Interactions, Mechanism of Action . DrugBank Online . 23 June 2017 . 31 August 2024.
13. Web site: norfenefrine . ChemSpider . 31 August 2024 . 31 August 2024.