Pholedrine

Pholedrine
Clinical data
Trade namesParedrinol, 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 InfoCard100.006.114 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 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 ☒N
  • Key:SBUQZKJEOOQSBV-UHFFFAOYSA-N ☒N
  (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]

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

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 INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and DCFTooltip Dénomination Commune Française, while foledrina is its DCITTooltip 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. ^ a b c d e f g Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 969. ISBN 978-3-88763-101-7. Retrieved 30 August 2024.
  2. ^ a b "Pholedrine". National Library of Medicine. Retrieved 24 June 2023.
  3. ^ a b 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. ^ a b c d e f 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. ^ a b 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.