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Norfenefrine

Sympathomimetic drug

Summary

Sympathomimetic drug

Field	Value
Verifiedfields	changed
verifiedrevid	462263073
image	Norfenefrine.png
image_class	skin-invert-image
width	200px
image2	(R)-Norfenefrine molecule ball.png
image_class2	bg-transparent
width2	200px
alt2	Ball-and-stick model of (R)-Norfenefrine
Drugs.com
legal_status	Rx-only
metabolism	m-Hydroxymandelic acid
CAS_number_Ref
CAS_number	536-21-0
CAS_supplemental
15308-34-6 (hydrochloride)
ATC_prefix	C01
ATC_suffix	CA05
PubChem	4538
ChemSpiderID_Ref
ChemSpiderID	4379
UNII_Ref
UNII	D2P3M6SRN5
KEGG_Ref
KEGG	D08286
ChEBI	134779
ChEMBL_Ref
ChEMBL	358040
DrugBank	DB13378
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_Ref
StdInChI	1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2
StdInChIKey_Ref
StdInChIKey	LRCXRAABFLIVAI-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

15308-34-6 (hydrochloride)

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 . 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

(1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology.
Elks, J.. (2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer US.
Macdonald F. (1997). "Dictionary of Pharmacological Agents". CRC Press.
(2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
(December 1977). "m-Octopamine, p-octopamine and phenylethanolamine in rat brain: a sensitive, specific assay and the effects of some drugs". Journal of Neurochemistry.
(November 1989). "Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders". Drugs.
(January 1998). "Midodrine. A review of its therapeutic use in the management of orthostatic hypotension". Drugs Aging.
(March 2007). "Orthostatic hypotension: evaluation and treatment". Cardiovasc Hematol Disord Drug Targets.
(June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". Br J Pharmacol.
"Norfenefrine".
(23 June 2017). "Norfenefrine: Uses, Interactions, Mechanism of Action".
(31 August 2024). "norfenefrine".

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-adrenergic-agonists antihypotensive-agents cardiac-stimulants norepinephrine-dopamine-releasing-agents neurotransmitters peripherally-selective-drugs 3-hydroxyphenyl-compounds phenylethanolamines sympathomimetics taar1-agonists trace-amines

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