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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
Identifiers
IUPAC name 3-(2-Amino-1-hydroxyethyl)phenol
CAS Number	536-21-0 15308-34-6 (hydrochloride)
PubChem CID	4538
DrugBank	DB13378
ChemSpider	4379
UNII	D2P3M6SRN5
KEGG	D08286
ChEBI	CHEBI:134779
ChEMBL	ChEMBL358040
CompTox Dashboard (EPA)	DTXSID3048314
ECHA InfoCard	100.007.844
Chemical and physical data
Formula	C8H11NO2
Molar mass	153.181 g·mol
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 Key:LRCXRAABFLIVAI-UHFFFAOYSA-N
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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). 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.

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.

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.

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.

Society and culture

Names

Norfenefrine is the generic name of the drug and its INNTooltip International Nonproprietary Name. 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.

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.

• Alpha-adrenergic agonists
• Antihypotensive agents
• Cardiac stimulants
• Norepinephrine-dopamine releasing agents
• Neurotransmitters
• Peripherally selective drugs
• 3-Hydroxyphenyl compounds
• Phenylethanolamines
• Sympathomimetics
• TAAR1 agonists
• Trace amines