Norfenefrine

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][6] 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.^[7]

Norfenefrine

Clinical data
Other names	Norfenephrine; Norphenephrine; Norphenylephrine; meta-Norsynephrine; meta-Octopamine; 3-Octopamine; Adrianol; 3,β-Dihydroxyphenethylamine; 3,β-Dihydroxy-β-phenylethylamine
AHFS/Drugs.com	International Drug Names
ATC code	C01CA05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	m-Hydroxymandelic acid[1][2]
Identifiers
IUPAC name 3-(2-Amino-1-hydroxyethyl)phenol
CAS Number	536-21-0 Y 15308-34-6 (hydrochloride)
PubChem CID	4538
DrugBank	DB13378
ChemSpider	4379 Y
UNII	D2P3M6SRN5
KEGG	D08286 Y
ChEBI	CHEBI:134779
ChEMBL	ChEMBL358040 Y
CompTox Dashboard (EPA)	DTXSID3048314
ECHA InfoCard	100.007.844
Chemical and physical data
Formula	C8H11NO2
Molar mass	153.181 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC(c1cc(O)ccc1)CN
InChI InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2 Y Key:LRCXRAABFLIVAI-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Medical uses

Norfenefrine is used in the treatment of hypotension (low blood pressure).^[3] It is said to be similarly effective or less effective than midodrine.^[8][9][10]

Pharmacology

Pharmacodynamics

Norfenefrine is described as an α-adrenergic receptor agonist and sympathomimetic agent.^[4][6] It is said to act predominantly as an α₁-adrenergic receptor agonist.^[3]

Chemistry

Norfenefrine, also known as 3,β-dihydroxyphenethylamine, is a substituted phenethylamine derivative.^[4][6] 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).^[4]

Norfenefrine is used medically as the hydrochloride salt.^[4][6]

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 INNTooltip International Nonproprietary Name.^[4][6] Synonyms of norfenefrine include hydroxyphenylethanolamine, nor-phenylephrine, and m-norsynephrine, among others.^[4][6] Brand names of norfenefrine include Novadral, A.S. COR, Coritat, Energona, Hypolind, Norfenefrin Ziethen, and Norfenefrin-Ratiopharm, among others.^[6]

Availability

Norfenefrine is marketed in Europe, Japan, and Mexico.^[6]

References

1. Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ (1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology. 283 (1): 93–106. doi:10.1007/bf00500148. PMID 4277715. S2CID 35523412.
2. D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, Leon A (January 2010). "Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–351. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. S2CID 12797090.
3. Docherty JR (June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". Br J Pharmacol. 154 (3): 606–622. doi:10.1038/bjp.2008.124. PMC 2439527. PMID 18500382.
4. Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 61. ISBN 978-1-4757-2085-3. Retrieved 22 July 2024.
5. Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 104. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
6. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.
7. Danielson TJ, Boulton AA, Robertson HA (December 1977). "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. doi:10.1111/j.1471-4159.1977.tb06519.x. PMID 340613. S2CID 26137006.
8. McTavish D, Goa KL (November 1989). "Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders". Drugs. 38 (5): 757–777. doi:10.2165/00003495-198938050-00004. PMID 2480881.
9. McClellan KJ, Wiseman LR, Wilde MI (January 1998). "Midodrine. A review of its therapeutic use in the management of orthostatic hypotension". Drugs Aging. 12 (1): 76–86. doi:10.2165/00002512-199812010-00007. PMID 9467688.
10. Maule S, Papotti G, Naso D, Magnino C, Testa E, Veglio F (March 2007). "Orthostatic hypotension: evaluation and treatment". Cardiovasc Hematol Disord Drug Targets. 7 (1): 63–70. doi:10.2174/187152907780059029. PMID 17346129.
11. "Norfenefrine". PubChem. Retrieved 31 August 2024.
12. "Norfenefrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 31 August 2024.
13. "norfenefrine". ChemSpider. 31 August 2024. Retrieved 31 August 2024.