ノルフェネフリン
- 関
- norfenefrine hydrochloride
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/10/01 23:07:32」(JST)
[Wiki en表示]
Norfenefrine
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Systematic (IUPAC) name |
3-(2-amino-1-hydroxyethyl)phenol |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
℞ Prescription only |
Identifiers |
CAS number |
536-21-0 N
15308-34-6 (hydrochloride) |
ATC code |
C01CA05 |
PubChem |
CID 4538 |
ChemSpider |
4379 Y |
UNII |
D2P3M6SRN5 Y |
KEGG |
D08286 Y |
ChEMBL |
CHEMBL358040 Y |
Synonyms |
Norfenephrine
Norphenephrine
Norphenylephrine
meta-Norsynephrine
meta-Octopamine
3-Octopamine |
Chemical data |
Formula |
C8H11NO2 |
Mol. mass |
153.178 g/mol |
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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
|
N (what is this?) (verify)
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Norfenefrine (INN; brand names Coritat, Energona, Hypolind, and Novadral), also known as m-octopamine (or 3-octopamine) and 3,β-dihydroxyphenethylamine, is an adrenergic agent used as a sympathomimetic drug which is marketed in Europe, Japan, and Mexico.[1][2] 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.[3]
See also
- Octopamine
- m-Tyramine
- Phenylephrine
- Metaraminol
References
- ^ F.. Macdonald (1997). = DeX7jgInYFMC&pg = PA104 Dictionary of Pharmacological Agents. CRC Press. p. 104. ISBN 978-0-412-46630-4. http://books.google.com/books?id = DeX7jgInYFMC&pg = PA104. Retrieved 24 April 2012.
- ^ = 5GpcTQD_L2oC&pg = PA750 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. http://books.google.com/books?id = 5GpcTQD_L2oC&pg = PA750. 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. PMID 340613.
Cardiac stimulants excluding cardiac glycosides (C01C)
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Adrenergic and
dopaminergic agents |
Adrenergic agonists |
α |
- Metaraminol
- Phenylephrine
- Methoxamine
- Norfenefrine
- Oxedrine
- Midodrine
- Mephentermine
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β |
- Dobutamine
- Arbutamine
- Isoprenaline
- Prenalterol
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mixed |
- Amezinium metilsulfate
- Epinephrine #
- Norepinephrine
- Etilefrine
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|
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Dopamine agonists |
|
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Both |
- Dopamine #
- Dopexamine
- Ibopamine
- Octopamine
|
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Unknown/ungrouped |
- Dimetofrine
- Gepefrine
- Cafedrine
- Theodrenaline
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|
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Phosphodiesterase inhibitors (PDE3I) |
- Amrinone
- Milrinone
- Enoximone
- Bucladesine
|
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Other cardiac stimulants |
- Angiotensinamide
- Xamoterol
- Levosimendan
- Pimobendan
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco/cong/tumr, sysi/epon, injr
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proc, drug (C1A/1B/1C/1D), blte
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Neurotransmitters
|
|
Amino acids |
- Alanine
- Aspartate
- Cycloserine
- DMG
- GABA
- Glutamate
- Glycine
- Hypotaurine
- Kynurenic acid (Transtorine)
- NAAG (Spaglumic acid)
- NMG (Sarcosine)
- Serine
- Taurine
- TMG (Betaine)
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Endocannabinoids |
- 2-AG
- 2-AGE (Noladin ether)
- AEA (Anandamide)
- NADA
- OAE (Virodhamine)
- Oleamide
- PEA (Palmitoylethanolamide)
- RVD-Hpα
- Hp (Hemopressin)
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Gasotransmitters |
- Carbon monoxide
- Hydrogen sulfide
- Nitric oxide
- Nitrous oxide
|
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Monoamines |
Dopamine
- Epinephrine (Adrenaline)
- Melatonin
- NAS (Normelatonin)
- Norepinephrine (Noradrenaline)
- Serotonin (5-HT)
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Purines |
|
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Trace amines |
- 3-ITA
- 5-MeO-DMT
- Bufotenin
- DMT
- m-Octopamine
- p-Octopamine
- m-Tyramine
- p-Tyramine
- NMT
- Phenethylamine
- Synephrine
- Thyronamine
- Tryptamine
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Others |
- 1,4-BD
- Acetylcholine
- GBL
- GHB
- Histamine
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See also Template:Neuropeptides
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anat(h/r/t/c/b/l/s/a)/phys(r)/devp/prot/nttr/nttm/ntrp
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noco/auto/cong/tumr, sysi/epon, injr
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Adrenergics
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Receptor ligands
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α1
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- Agonists: 5-FNE
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Cirazoline
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Levonordefrin
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- CI-926
- Corynanthine
- Dapiprazole
- DL-017
- Domesticine
- Doxazosin
- Eugenodilol
- Fenspiride
- GYKI-12,743
- GYKI-16,084
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- Mephendioxan
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Nicergoline
- Niguldipine
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- RS-97,078
- SGB-1,534
- Silodosin
- SL-89.0591
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tibalosin
- Tiodazosin
- Tipentosin
- Tolazoline
- Trimazosin
- Upidosin
- Urapidil
- Zolertine
- Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
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α2
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- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Esproquin
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Levonordefrin
- Lofexidine
- Medetomidine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
Antagonists: 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- GYKI-12,743
- GYKI-16,084
- Idazoxan
- Mianserin
- Mirtazapine
- MK-912
- NAN-190
- Olanzapine
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269,970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
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β
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Reuptake inhibitors
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NET
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- Selective norepinephrine reuptake inhibitors: Amedalin
- Atomoxetine (Tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine
- Bupropion (Amfebutamone)
- Fencamine
- Fencamfamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- JNJ-7925476
- JZ-IV-10
- Methylnaphthidate
- Naphyrone
- NS-2359
- PRC200-SS
- SEP-225,289
- SEP-227,162
- Tesofensine; Tricyclic antidepressants: Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- melitracen
- Nortriptyline
- Protriptyline
- Trimipramine; Tetracyclic antidepressants: Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline; Others: Cocaine
- CP-39,332
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
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VMAT
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme inhibitors
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Anabolism
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PAH
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TH
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- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
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AAAD
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- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
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DBH
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- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
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PNMT
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- CGS-19281A
- SKF-64139
- SKF-7698
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Catabolism
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MAO
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- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids (Harmine,
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective:
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also [[D-Deprenyl]])
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
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COMT
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- Entacapone
- Nitecapone
- Tolcapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
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Cofactors
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- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
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Others
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- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
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List of adrenergic drugs
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TAAR Ligands
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TAAR1 |
Agonists
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Selective: O-Phenyl-3-iodotyramine • RO5166017; Non-selective: 3-Iodothyronamine • 3-Methoxytyramine • 5-MeO-DMT • Amphetamine • Apomorphine • Bromocriptine • Bufotenin • DMT • DOI • Dopamine • LSD • m-Octopamine • m-Tyramine • MDMA • Methamphetamine • N-Methylphenethylamine • N-Methyltryptamine • N-Methyltyramine • Nomifensine • Norepinephrine • p-Octopamine • p-Tyramine • Phenethylamine • Serotonin • Synephrine • Tryptamine; Unknown: RG7351
* Note that many other phenethylamines, tryptamines, ergolines, and thyronamines are either known to or are likely to act as non-selective TAAR1 agonists as well.
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Antagonists
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Selective: EPPTB (RO5212773)
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English Journal
- A multichannel electrophoresis microchip platform for rapid chiral selector screening.
- Gao Y, Luo Y, Qin J, Lin B.SourceDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, P. R. China.
- Electrophoresis.Electrophoresis.2008 May;29(9):1918-23.
- This study presents a four-channel electrophoresis chip platform, featuring double-cross hydrostatic sample injection, for rapid chiral selector screening. This platform needs only five electrodes to drive microchip electrophoresis in four separate channels for screening four chiral selectors at a t
- PMID 18384040
- A new copper(I)-tetrahydrosalen-catalyzed asymmetric Henry reaction and its extension to the synthesis of (S)-norphenylephrine.
- Xiong Y, Wang F, Huang X, Wen Y, Feng X.SourceKey Laboratory of Green Chemistry and Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2007;13(3):829-33.
- A new chiral hydrogenated salen catalyst has been developed for the asymmetric Henry reaction which produces the expected products in moderate to high yields (up to 98 %) with excellent enantioselectivities (up to 96 % ee). A variety of aromatic, heteroaromatic, enal, and aliphatic aldehydes were fo
- PMID 17068834
Japanese Journal
- 心筋障害と血中酸素分圧との関連におけるSympathomimetic Aminesの作用
- 沢辺 隆司,府川 和永,佐藤 進
- 藥學雜誌 101(2), 161-168, 1981-02-25
- … The decrease in Po_2 due to dl-norfenefrine, which causes very little cardiac lesion and acts on the α-receptor, was not significant. …
- NAID 110003650127
Related Links
- InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2 Yes Y Key:LRCXRAABFLIVAI-UHFFFAOYSA-N Yes Y. N (what is this?) (verify). Norfenefrine (INN; brand names Coritat, Energona, Hypolind, and Novadral), also known ...
Related Pictures
★リンクテーブル★
[★]
- 英
- norfenefrine、norfenefrine hydrochloride
- 関
- 塩酸ノルフェネフリン
[★]
- 関
- norfenefrine