Antihypotensive medication
Pharmaceutical compound
Metaraminol Clinical data Trade names Aramine, Metaramin, Pressonex, others Other names Metaradrine; Hydroxynorephedrine;m -Hydroxypropadrine;m -Hydroxynorephedrine;meta -Hydroxynorephedrine; 3-Hydroxyphenylisopropanolamine; (1R ,2S )-3,β-Dihydroxy-α-methylphenethylamine; (1R ,2S )-3,β-Dihydroxyamphetamine AHFS /Drugs.com International Drug Names License data Pregnancy Routes of Intramuscular injection ,intravenous administration [ 1] Drug class Norepinephrine releasing agent ;Adrenergic receptor agonist ;Sympathomimetic ;Antihypotensive ATC code Legal status Legal status Pharmacokinetic dataProtein binding 45% Metabolism Liver Identifiers CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) Chemical and physical data Formula C 9 H 13 N O 2 Molar mass −1 3D model (JSmol ) InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
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Metaraminol , also known asmetaradrine and sold under the brand nameAramine among others, is asympathomimetic medication which is used in the prevention and treatment ofhypotension (low blood pressure), particularly as a complication ofanesthesia .[ 1] [ 3] [ 4] intramuscular orintravenous administration .[ 1]
Side effects of metaraminol includereflex bradycardia among others. Metaraminol is anorepinephrine releasing agent and at high doses aα1 -adrenergic receptor agonist with someβ-adrenergic effect.[ 5] [ 6] [ 7] substituted amphetamine and is closely related tophenylpropanolamine ,ephedrine , andoxilofrine .[ 3] [ 4]
Metaraminol was approved for medical use in the United States in September 1954.[ 8] [ 9] [ 10]
A commercially prepared pre-filled syringe of metaraminol for bolus use during anaesthesia, made up as 0.5 mg/mL (2.5 mg in 5 mL). Metaraminol is givenintravenously as either a bolus (often 0.5–1 mg doses) or as an infusion, usually via peripheral intravenous access. Metaraminol is commonly available as 10 mg in 1 mL, that requires dilution prior to administration (often made up to a 0.5 mg/mL solution), however pre-prepared syringes of metaraminol for bolus use for hypotension are also commonly available.[ 11] [ 12]
Metaraminol is also used in the treatment ofpriapism .[ 13] [ 14] [ 15]
The dominantmechanism of action for thevasopressor action of metaraminol is indirect,[ 5] norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects.[ 6] α-adrenergic agonist andβ1 -adrenergic agonist effects.[ 5] α1 -adrenergic effects predominate, such thatreflex bradycardia is a common side effect.
Metaraminol, also known as (1R ,2S )-3,β-dihydroxy-α-methylphenethylamine or as (1R ,2S )-3,β-dihydroxyamphetamine, is asubstituted phenethylamine andamphetamine derivative .[ 3] [ 4] R ,2S )-enantiomer ofmeta -hydroxynorephedrine[ 3] [ 4] phenylpropanolamine ((1RS ,2SR )-β-hydroxyamphetamine; norephedrine),ephedrine ((1R ,2S )-β-hydroxy-N -methylamphetamine),para -hydroxynorephedrineoxilofrine (4,β-dihydroxy-N -methylamphetamine).[ 3] [ 4]
The experimentallog P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07.[ 16] [ 17]
Metaraminol is usedpharmaceutically as thebitartrate salt .[ 3] [ 4]
Metaraminol was approved for medical use in the United States in September 1954.[ 8] [ 9] [ 10] [ 3]
Society and culture [ edit ] Metaraminol is thegeneric name of the medication and itsINN Tooltip International Nonproprietary Name andBAN Tooltip British Approved Name , while itsDCF Tooltip Dénomination Commune Française is métaraminol and itsDCIT Tooltip Denominazione Comune Italiana is metaraminolo.[ 3] [ 4] [ 18] bitartrate salt , its generic name is metaraminol bitartrate and this is itsUSAN Tooltip United States Adopted Name andJAN Tooltip Japanese Accepted Name , while metaraminol tartrate is itsBANM Tooltip British Approved Name .[ 3] [ 4] [ 18] [ 4] [ 18] [ 3] [ 4] [ 18]
^a b c d "Injection : Aramine (Metaraminol Bitartrate)" (PDF) .U.S.Food and Drug Administration (FDA) . Retrieved12 March 2022 .^ "Metaraminol Bitartrate Injection, USP" .DailyMed . Retrieved12 April 2025 .^a b c d e f g h i j Elks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 . Retrieved31 August 2024 . ^a b c d e f g h i j Schweizerischer Apotheker-Verein (2000).Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 . Retrieved31 August 2024 . ^a b c "Metaraminol" .Deranged Physiology . Retrieved19 October 2022 .^a b Harrison DC, Chidsey CA, Braunwald E (September 1963). "Studies on the Mechanism of Action of Metaraminol (Aramine)".Annals of Internal Medicine .59 (3):297– 305.doi :10.7326/0003-4819-59-3-297 .PMID 14065947 . ^ Kee VR (August 2003)."Hemodynamic pharmacology of intravenous vasopressors" Crit Care Nurse .23 (4):79– 82.doi :10.4037/ccn2003.23.4.79 .PMID 12961786 . ^a b "Aaramine: FDA-Approved Drugs" .U.S.Food and Drug Administration (FDA) . Retrieved12 April 2025 .^a b Weil MH, Spink WW (June 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). I. Observations in normotensive subjects".Am J Med Sci .229 (6):661– 669.doi :10.1097/00000441-195506000-00008 .PMID 14376394 . ^a b Weil MH (October 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). II. Observations on its use in the management of shock".The American Journal of the Medical Sciences .230 (4):357– 369.doi :10.1097/00000441-195510000-00001 .PMID 13258566 . ^ "Metaraminol 0.5 mg/ml, Solution for Injection in pre-filled syringe - Summary of Product Characteristics (SmPC) - (emc)" .www.medicines.org.uk . Retrieved19 October 2022 .^ Goodrick N, Wentrup T, Messer G, Gleeson P, Culwick M, Goulding G (21 August 2020)."Pre-filled emergency drugs: The introduction of pre-filled metaraminol and ephedrine syringes into the main operating theatres of a major metropolitan centre" .Australasian Anaesthesia (2013):127– 134. ^ McDonald M, Santucci R (2004)."Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol" .Int Braz J Urol .30 (2):121– 122.doi :10.1590/S1677-55382004000200007 PMID 15703094 . ^ Koga S, Shiraishi K, Saito Y (1990). "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). "[Metaraminol in therapy of various forms of priapism]".Urologe A .27 (4):225– 9.PMID 3140463 . ^ "Metaraminol" .PubChem . Retrieved1 September 2024 .^ "Metaraminol" .ChemSpider . 1 September 2024. Retrieved1 September 2024 .^a b c d "Metaraminol - Drugs.com" .www.drugs.com .
α1
Agonists Antagonists Abanoquil ADRIANA Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g.,brexpiprazole ,clozapine ,olanzapine ,quetiapine ,risperidone )Benoxathian Beta blockers (e.g.,adimolol ,amosulalol ,arotinolol ,carvedilol ,eugenodilol ,labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g.,acetergamine ,ergotamine ,dihydroergotamine ,lisuride ,nicergoline ,terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,imipramine ,trimipramine )Trimazosin Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Urapidil WB-4101 Zolertine
α2
Agonists Antagonists 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g.,asenapine ,brexpiprazole ,clozapine ,lurasidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,zotepine )Azapirones (e.g.,buspirone ,gepirone ,ipsapirone ,tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Yohimbine
β
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )
