Metaraminol

Metaraminol
Clinical data
Trade namesAramine, 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.comInternational Drug Names
License data
Pregnancy
category
  • AU: C
Routes of
administration		Intramuscular injection, intravenous administration[1][2]
Drug classNorepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding45%[2]
MetabolismLiver[2]
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
FormulaC9H13NO2
Molar mass167.208 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 checkY
  • Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N checkY
  (verify)

Metaraminol, also known as metaradrine and sold under the brand names Aramine and Pressonex 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][4][5] It is given by intramuscular or intravenous administration.[1][2]

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.[6][7][8] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.[4][5]

Metaraminol was first described and introduced for medical use by 1955.[9][10]

  1. ^ a b c https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf
  2. ^ a b c d Cite error: The named reference DrugBank was invoked but never defined (see the help page).
  3. ^ "Injection : Aramine (Metaraminol Bitartrate)" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 12 March 2022.
  4. ^ a b Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid14065947 was invoked but never defined (see the help page).
  8. ^ 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.
  9. ^ Cite error: The named reference WeilSpink1955 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Weil1955 was invoked but never defined (see the help page).