Metaraminol definition and meaning

Metaraminol

From Wikipedia, the free encyclopedia

Metaraminol
Systematic (IUPAC) name

(1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
Identifiers
CAS number	54-49-9
ATC code	C01CA09
PubChem	5906
DrugBank	APRD00555
Chemical data
Formula	C₉H₁₃N O₂
Mol. mass	167.205 g/mol
Pharmacokinetic data
Bioavailability	n/a
Protein binding	~45%
Metabolism	Hepatic
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	C(AU) C(US)
Legal status	POM (UK)
Routes	Intravenous
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Metaraminol (INN, trade name Aramine) is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia.It is an α₁-adrenergic receptor agonist with some β effect.

Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.^[1]^[2]^[3]

References

^ McDonald M, Santucci R (2004). [Expression error: Missing operand for > "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol."]. Int Braz J Urol 30 (2): 121–2. doi:10.1590/S1677-55382004000200007. PMID 15703094.
^ Koga S, Shiraishi K, Saito Y (1990). [Expression error: Missing operand for > "Post-traumatic priapism treated with metaraminol bitartrate: case report."]. J Trauma 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). [Expression error: Missing operand for > "[Metaraminol in therapy of various forms of priapism]"]. Urologe A 27 (4): 225–9. PMID 3140463.

Adrenergics

Receptor
Ligands

α₁

Agonists: Amidephrine • Anisodamine • Anisodine • Cirazoline • Dopamine • Ephedrine • Epinephrine (Adrenaline) • Etilefrine • Indanidine • Isoprenaline • Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Midodrine • Naphazoline • Norepinephrine (Noradrenaline) • Octopamine • Oxymetazoline • Phenylephrine • Phenylpropanolamine • Pseudoephedrine • Synephrine • Tetrahydrozoline
Antagonists: Alfuzosin • Arotinolol • Carvedilol • Dihydroergotamine • Doxazosin • Ergotamine • Indoramin • L-765,314 • Labetalol • Moxisylyte • Nantenine • Phentolamine • Phenoxybenzamine • Prazosin • Quetiapine • Silodosin • Talipexole • Tamsulosin • Terazosin • Tolazoline • Trimazosin • Urapidil

α₂

Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • Amitraz • Apraclonidine • Brimonidine • Clonidine • Detomidine • Dexmedetomidine • Dihydroergotamine • Dopamine • Ephedrine • Ergotamine • Epinephrine (Adrenaline) • Etilefrine • Guanabenz • Guanfacine • Guanethidine • Guanoxabenz • Levonordefrin • Lofexidine • Medetomidine • Methyldopa • Mivazerol • Naphazoline • Norepinephrine (Noradrenaline) • Phenylpropanolamine • Pseudoephedrine • Rilmenidine • Romifidine • Talipexole • Tetrahydrozoline • Tizanidine • Tolonidine • Xylazine • Xylometazoline
Antagonists: 1-PP • Atipamezole • BRL-44408 • Buspirone • Cirazoline • Efaroxan • Gepirone • Idazoxan • Ipsapirone • Mianserin • Mirtazapine • NAN-190 • Phentolamine • Phenoxybenzamine • Quetiapine • Rauwolscine • SB-269,970 • Setiptiline • Spiroxatrine • Tandospirone • Tolazoline • Yohimbine

β₁	Agonists: Denopamine • Dobutamine • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) Antagonists: Acebutolol • Alprenolol • Amosulalol • Arotinolol • Atenolol • Bupranolol • Carvedilol • Celiprolol • Betaxolol • Bisoprolol • Dichloroisoprenaline • Esmolol • Labetalol • Metipranolol • Metoprolol • Nadolol • Nebivolol • Oxprenolol • Penbutolol • Pindolol • Practolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol • Xamoterol
β₂	Agonists: Arformoterol • Bambuterol • Bitolterol • Carbuterol • Clenbuterol • Dopamine • Dopexamine • Epinephrine (Adrenaline) • Etilefrine • Fenoterol • Formoterol • Hexoprenaline • Indacaterol • Levonordefrin • Levosalbutamol • Methyldopa • Norepinephrine (Noradrenaline) • Orciprenaline • Pirbuterol • Procaterol • Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Terbutaline • Tulobuterol Antagonists: Alprenolol • Amosulalol • Arotinolol • Bupranolol • Butaxamine • Carvedilol • Dichloroisoprenaline • ICI 118551 • Labetalol • Metipranolol • Nadolol • Oxprenolol • Penbutolol • Pindolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol
β₃	Agonists: Amibegron • Arotinolol • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Labetalol • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) • Solabegron Antagonists: Carvedilol • SR 59230A
β_?	Agonists: Arbutamine • BAAM • Befunolol • Broxaterol • Buphenine • Cimaterol • Ephedrine • Higenamine • Isoetarine • Isoxsuprine • Mabuterol • Methoxyphenamine • Oxyfedrine • Phenylpropanolamine • Prenalterol • Pseudoephedrine • Ractopamine • Tretoquinol • Zilpaterol • Zinterol

Reuptake
Inhibitors

Plasmalemmal

NET Inhibitors

Norepinephrine Reuptake Inhibitors: Atomoxetine (Tomoxetine) • Ciclazindol • Mazindol • Nisoxetine • Reboxetine • Tandamine • Tapentadol • Viloxazine; Norepinephrine-Dopamine Reuptake Inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • LR-5182 • Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-Norepinephrine Reuptake Inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Sibutramine • Tramadol • 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 • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline • Setiptiline; Others: Cocaine • Nefazodone • Nefopam • Ziprasidone

TRPC6 Activators

Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing
Agents

Morpholines: Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion, Amfepramone) • D-Deprenyl • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ephedrine (EPH) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Indanorex • L-Deprenyl (Selegiline) • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Mephentermine • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Ortetamine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA) • Paredrine (Norpholedrine, Oxamphetamine) • Phenethylamine (PEA) • Pholedrine • Phenpentermine • Phenpromethamine • Phentermine • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) • Parafluorophenylpiperazine (pFPP; Fluoperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 2-Benzylpiperidine (2-BP) • 4-Benzylpiperidine (4-BP) • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanylaminopropane (IAP) • Isometheptene • Methylhexanamine • Naphthylaminopropane (NAP) • Octodrine • Phthalimidopropiophenone • Propylhexedrine (PHX) • Tuaminoheptane (Tuamine)

Enzyme
Inhibitors

Anabolism

PAH Inhibitors	3,4-Dihydroxystyrene
TH Inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone
AAAD Inhibitors	Benserazide • Carbidopa
DBH Inhibitors	Disulfiram • Nepicastat • Tropolone
PNMT Inhibitors	CGS-19281A • SKF-64139 • SKF-7698

Catabolism

MAO Inhibitors

Nonselective: Benmoxin • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Metralindole • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: D-Deprenyl • L-Deprenyl (Selegiline) • Ladostigil • Lazabemide • Pargyline • Rasagiline
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT Inhibitors

Entacapone • Tolcapone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine • L-DOPS (Droxidopa)
Cofactors	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⁺)
Others	Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Release Blockers: Bretylium • Guanethidine

v • d • e Phenethylamines
Phenethylamines	Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • DMPEA • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2 Stimulants: 2-OH-PEA • α-Et-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA) Entactogens: Lophophine • MDPEA • MDMPEA
Amphetamines	Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • Psi-DOM • TMA • TeMA Stimulants: 4-MA • 4-MMA • 4-MTA • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • D-Deprenyl • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • L-Deprenyl (Selegiline) • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine Entactogens: MDA • MDEA ("Eve") • MDHMA (FLEA) • MDMA ("Ecstasy", "Adam") • MDOH • MMDA • MMDMA
Phentermines	Stimulants: Chlorphentermine • Clortermine • Mephentermine • Phenpentermine • Phentermine Entactogens: MDPH • MDMPH
Cathinones	Stimulants: Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone Entactogens: Ethylone • Methylone
Butanamines	Entactogens: BDB (J) • BOH (Hydroxy-J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • MBDB (Methyl-J; "Eden")
Catecholamines (and relatives..)	6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • Octopamine • Tyramine
Miscellaneous	Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Etilefrine • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Methoxamine • Methoxyphenamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol

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