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]