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Norfenefrine

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From Wikipedia, the free encyclopedia

Sympathomimetic drug

Pharmaceutical compound

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)
PubChemCID	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)

Norfenefrine, also known asmeta-octopamine ornorphenylephrine and sold under the brand nameNovadral among others, is asympathomimetic medication which is used in the treatment ofhypotension (low blood pressure).^[3]^[4]^[5]^[6] Along with itsstructural isomer p-octopamine and thetyramines, norfenefrine is anaturally occurring endogenous trace amine and plays a role as a minorneurotransmitter in thebrain.^[7]

Medical uses

[edit]

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

Pharmacology

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Pharmacodynamics

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Norfenefrine is described as anα-adrenergic receptor agonist andsympathomimetic agent.^[4]^[6] It is said to act predominantly as anα₁-adrenergic receptor agonist.^[3]

Chemistry

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Norfenefrine, also known as 3,β-dihydroxyphenethylamine, is asubstituted phenethylamine derivative.^[4]^[6] It is ananalogue ofnorepinephrine (3,4,β-trihydroxyphenethylamine), ofmeta-tyramine (3-hydroxyphenethylamine), ofphenylephrine ((R)-β,3-dihydroxy-N-methylphenethylamine), ofetilefrine (3,β-dihydroxy-N-ethylphenethylamine), and ofmetaterol (3,β-dihydroxy-N-isopropylphenethylamine), as well as ofmetaraminol ((1R,2S)-3,β-dihydroxy-α-methylphenethylamine).^[4]

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

The predictedlog P of norfenefrine is -0.28 to -0.95.^[11]^[12]^[13]

Society and culture

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Names

[edit]

Norfenefrine is thegeneric name of the drug and its INNTooltip International Nonproprietary Name.^[4]^[6] Synonyms of norfenefrine includehydroxyphenylethanolamine,nor-phenylephrine, andm-norsynephrine, among others.^[4]^[6] Brand names of norfenefrine includeNovadral,A.S. COR,Coritat,Energona,Hypolind,Norfenefrin Ziethen, andNorfenefrin-Ratiopharm, among others.^[6]

Availability

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Norfenefrine is marketed inEurope,Japan, andMexico.^[6]

References

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^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.
^^a ^b ^cDocherty 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.
^^a ^b ^c ^d ^e ^f ^gElks, J. (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 61.ISBN 978-1-4757-2085-3. Retrieved22 July 2024.
^Macdonald F (1997).Dictionary of Pharmacological Agents. CRC Press. p. 104.ISBN 978-0-412-46630-4. Retrieved24 April 2012.
^^a ^b ^c ^d ^e ^f ^g ^hIndex Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750.ISBN 978-3-88763-075-1. Retrieved24 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.
^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.
^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.
^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.
^"Norfenefrine".PubChem. Retrieved31 August 2024.
^"Norfenefrine: Uses, Interactions, Mechanism of Action".DrugBank Online. 23 June 2017. Retrieved31 August 2024.
^"norfenefrine".ChemSpider. 31 August 2024. Retrieved31 August 2024.

Cardiac stimulants excluding cardiac glycosides (C01C)

Adrenergic and
dopaminergic agents

Adrenergic agonists

α	Denopamine Metaraminol Methoxamine Midodrine Norfenefrine Oxedrine Phenylephrine
β	Arbutamine Dobutamine Isoprenaline Prenalterol
mixed	Amezinium metilsulfate Droxidopa Epinephrine # Etilefrine Norepinephrine

Dopamine agonists

Fenoldopam

Both

Unknown/ungrouped

Phosphodiesterase inhibitors (PDE3I)

Other cardiac stimulants

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Neurotransmitters

Amino acid-derived

Major excitatory /
inhibitory systems

Glutamate system	Agmatine Aspartic acid (aspartate) Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine
GABA system	GABA GABOB GHB
Glycine system	α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine
GHB system	GHB T-HCA (GHC)

Biogenic amines

Monoamines	6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT)
Trace amines	3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine
Others	Histamine

Neuropeptides

Seehere instead.

Lipid-derived

Endocannabinoids

Neurosteroids

Seehere instead.

Nucleobase-derived

Nucleosides

Adenosine system	ADP AMP ATP

Vitamin-derived

Miscellaneous

Cholinergic system	Acetylcholine

Gasotransmitters	Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO)

Candidates	Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also:Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Trace amine-associated receptor modulators

TAAR1Tooltip Trace amine-associated receptor 1

EPPTB (RO-5212773)

TAAR5Tooltip Trace amine-associated receptor 5

Agonists	N,N-Dimethylethylamine Trimethylamine
Inverse agonists	3-Iodothyronamine

Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages.See also:Receptor/signaling modulators

v t e Phenethylamines
Phenethylamines	Psychedelics:25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants:Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens:Lophophine MDPEA MDMPEA Others:Biscaline BOH Buscaline DMPEA
Amphetamines	Psychedelics:3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants:2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine,Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine,Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine,Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens:4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others:3,4-DCA Amiflamine DiFMDA Selegiline (alsoD-Deprenyl)
Phentermines	Stimulants:Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens:MDPH MDMPH Others:Cericlamine
Cathinones	Stimulants:3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens:3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone
Phenylisobutylamines	Entactogens:4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants:Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants:α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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