Norfenefrine

Norfenefrine
Clinical data
Other names	Norfenephrine; Norphenephrine; Norphenylephrine; meta-Norsynephrine; meta-Octopamine; 3-Octopamine
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;
ChemSpider	4379 ;
UNII	D2P3M6SRN5;
KEGG	D08286 ;
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 ;
	(what is this?)

Norfenefrine (INN; also known as meta-octopamine, 3-octopamine, and 3,β-dihydroxyphenethylamine) is an adrenergic agent used as a sympathomimetic drug which is marketed in Europe, Japan, and Mexico.^[3]^[4] 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.^[5]

Some brand names for it include Coritat, Energona, Hypolind, and Novadral.

References[]

^ Hengstmann, J. H.; Konen, W; Konen, C; Eichelbaum, M; Dengler, H. J. (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, Giovanni; Nordera, Gianpietro; Pizzolato, Gilberto; Bolner, Andrea; Colavito, Davide; Flaibani, Raffaella; Leon, Alberta (2010). "Trace amine metabolism in Parkinson's disease: Low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–51. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. S2CID 12797090.
^ 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): 1131–5. doi:10.1111/j.1471-4159.1977.tb06519.x. PMID 340613. S2CID 26137006.

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[pmid4277715-1] Hengstmann, J. H.; Konen, W; Konen, C; Eichelbaum, M; Dengler, H. J. (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] ’Andrea, Giovanni; Nordera, Gianpietro; Pizzolato, Gilberto; Bolner, Andrea; Colavito, Davide; Flaibani, Raffaella; Leon, Alberta (2010). "Trace amine metabolism in Parkinson's disease: Low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–51. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. S2CID 12797090.

[Macdonald1997-3] 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-4] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.

[pmid340613-5] 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): 1131–5. doi:10.1111/j.1471-4159.1977.tb06519.x. PMID 340613. S2CID 26137006.

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v t Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 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-iP 2C-N 2C-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-28 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: BOH 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 (also D-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
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

Clinical data


Other names	Norfenephrine Norphenephrine Norphenylephrine meta-Norsynephrine meta-Octopamine 3-Octopamine
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^N 15308-34-6 (hydrochloride)
PubChem CID	4538
ChemSpider	4379^Y
UNII	D2P3M6SRN5
KEGG	D08286^Y
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?)

Norfenefrine

See also[]

References[]