Metaraminol

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Metaraminol
Metaraminol Structural Formulae.png
Clinical data
Trade names Aramine, Metaramin, Pressonex, others
Other namesMetaradrine; 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
category
  • AU:C
Routes of
administration 		Intramuscular injection, intravenous administration [1]
Drug class Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 45%
Metabolism Liver
Identifiers
  • (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C9H13NO2
Molar mass 167.208 g·mol−1
3D model (JSmol)
  • O[C@H](c1cc(O)ccc1)[C@@H](N)C
  • 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 Yes check.svgY
  • Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N Yes check.svgY
   (verify)

Metaraminol, also known as metaradrine and sold under the brand name Aramine among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia. [1] [3] [4] It is given by intramuscular or intravenous administration. [1]

Contents

Side effects of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a α1-adrenergic receptor agonist with some β-adrenergic effect. [5] [6] [7] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine. [3] [4]

Metaraminol was approved for medical use in the United States in September 1954. [8] [9] [10]

Medical uses

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 prefilledsyringe.jpg
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 given intravenously 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 of priapism. [13] [14] [15]

Pharmacology

Pharmacodynamics

The dominant mechanism of action for the vasopressor action of metaraminol is indirect, [5] with metaraminol displacing norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects. [6] Metaraminol at higher doses may have direct α-adrenergic agonist and β1-adrenergic agonist effects. [5] However at doses common in clinical practice, the indirect α1-adrenergic effects predominate, such that reflex bradycardia is a common side effect.

Chemistry

Metaraminol, also known as (1R,2S)-3,β-dihydroxy-α-methylphenethylamine or as (1R,2S)-3,β-dihydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. [3] [4] It is the (1R,2S)-enantiomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine). [3] [4] The drug is closely related to phenylpropanolamine ((1RS,2SR)-β-hydroxyamphetamine; norephedrine), ephedrine ((1R,2S)-β-hydroxy-N-methylamphetamine), para-hydroxynorephedrine (4,β-dihydroxyamphetamine), and oxilofrine (4,β-dihydroxy-N-methylamphetamine). [3] [4]

The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07. [16] [17]

Metaraminol is used pharmaceutically as the bitartrate salt. [3] [4]

History

Metaraminol was approved for medical use in the United States in September 1954. [8] [9] [10] [3]

Society and culture

Names

Metaraminol is the generic name of the medication and its INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name, while its DCF Tooltip Dénomination Commune Française is métaraminol and its DCIT Tooltip Denominazione Comune Italiana is metaraminolo. [3] [4] [18] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USAN Tooltip United States Adopted Name and JAN Tooltip Japanese Accepted Name, while metaraminol tartrate is its BANM Tooltip British Approved Name. [3] [4] [18] A synonym of metaraminol is metaradrine. [4] [18] Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others. [3] [4] [18]

References

  1. 1 2 3 4 "Injection : Aramine (Metaraminol Bitartrate)" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 12 March 2022.
  2. ↑ "Metaraminol Bitartrate Injection, USP". DailyMed. Retrieved 12 April 2025.
  3. 1 2 3 4 5 6 7 8 9 10 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 62. ISBN   978-1-4757-2085-3 . Retrieved 31 August 2024.
  4. 1 2 3 4 5 6 7 8 9 10 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 660. ISBN   978-3-88763-075-1 . Retrieved 31 August 2024.
  5. 1 2 3 "Metaraminol". Deranged Physiology. Retrieved 19 October 2022.
  6. 1 2 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.
  7. ↑ 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.
  8. 1 2 "Aaramine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 12 April 2025.
  9. 1 2 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.
  10. 1 2 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.
  11. ↑ "Metaraminol 0.5 mg/ml, Solution for Injection in pre-filled syringe - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 19 October 2022.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ "Metaraminol". PubChem. Retrieved 1 September 2024.
  17. ↑ "Metaraminol". ChemSpider. 1 September 2024. Retrieved 1 September 2024.
  18. 1 2 3 4 "Metaraminol - Drugs.com". www.drugs.com.
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