Norfenefrine

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−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 ; 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).^[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]

^ 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.
^ 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.
^ Cite error: The named reference Docherty2008 was invoked but never defined (see the help page).
^ 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.
^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 104. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.
^ 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.

[HengstmannKonenKonen1974-1] 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.

[D'AndreaNorderaPizzolato2010-2] 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.

[Docherty2008-3] Cite error: The named reference Docherty2008 was invoked but never defined (see the help page).

[Elks2014-4] 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.

[Macdonald1997-5] Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 104. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.

[IndexNominum2000-6] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.

[pmid340613-7] 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.

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