Pholedrine

Last updated

Pholedrine
Pholedrine2D.svg
Clinical data
Trade names Paredrinol, Presoitan, Pulsotyl, Veritain, Veritol
Other names4-Hydroxy-N-methylamphetamine; 4-HMA; 4-Hydroxymethamphetamine; para-Hydroxymethamphetamine; PHMA; Hydroxymethamphetamine
Routes of
administration 		Topical (ocular)
Identifiers
  • 4-[2-(Methylamino)propyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.114 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H15NO
Molar mass 165.236 g·mol−1
3D model (JSmol)
  • Oc1ccc(cc1)CC(NC)C
  • InChI=1S/C10H15NO/c1-8(11-2)7-9-3-5-10(12)6-4-9/h3-6,8,11-12H,7H2,1-2H3 X mark.svgN
  • Key:SBUQZKJEOOQSBV-UHFFFAOYSA-N X mark.svgN
   (verify)

Pholedrine, also known as 4-hydroxy-N-methylamphetamine and sold under the brand names Paredrinol, Pulsotyl, and Veritol among others, is a sympathomimetic drug used in topical eye drops to dilate the pupil. [1] [2] [3] It can be used to diagnose Horner's syndrome. [3]

Contents

In 2004, it remained marketed only in Germany. [1] [ needs update ]

Pharmacology

Pharmacodynamics

Pholedrine is described as a sympathomimetic, antihypotensive, and ephedrine-like agent. [4] [1] [5]

Chemistry

Pholedrine, also known as 4-hydroxy-N-methylamphetamine, is a substituted phenethylamine and amphetamine derivative. [4] [1] It is structurally related to methamphetamine (N-methylamphetamine), norpholedrine (4-hydroxyamphetamine), oxilofrine (4,β-dihydroxy-N-methylamphetamine), and tyramine (4-hydroxyphenethylamine).

It is used pharmaceutically as the sulfate salt. [1] [4]

The predicted log P of pholedrine ranges from 1.12 to 1.7. [2] [6] [7]

History

Pholedrine was synthesized by 1951. [4]

Society and culture

Names

Pholedrine is the generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, and DCF Tooltip Dénomination Commune Française, while foledrina is its DCIT Tooltip Denominazione Comune Italiana. [4] [1] [5] The drug has been sold under brand names including Pholedrin Liquidum, Pholedrin-Longo-Isis, Presoitan, Veritain, and Veritol among others. [4] [1]

Other drugs

Pholedrine (4-hydroxymethamphetamine) is also a major metabolite of methamphetamine.

References

  1. 1 2 3 4 5 6 7 Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 969. ISBN   978-3-88763-101-7 . Retrieved 30 August 2024.
  2. 1 2 "Pholedrine". National Library of Medicine. Retrieved 24 June 2023.
  3. 1 2 Bates AT, Chamberlain S, Champion M, Foley L, Hughes E, Jani B, et al. (February 1995). "Pholedrine: a substitute for hydroxyamphetamine as a diagnostic eyedrop test in Horner's syndrome". Journal of Neurology, Neurosurgery, and Psychiatry. 58 (2): 215–217. doi:10.1136/jnnp.58.2.215. PMC   1073320 . PMID   7876854.
  4. 1 2 3 4 5 6 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 794. ISBN   978-1-4757-2085-3 . Retrieved 30 August 2024.
  5. 1 2 Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 219. ISBN   978-94-011-4439-1 . Retrieved 30 August 2024.
  6. ↑ "Metabolite 4-hydroxymethamphetamine". DrugBank Online. Retrieved 30 August 2024.
  7. ↑ "Pholedrine". ChemSpider. 21 July 2022. Retrieved 30 August 2024.
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