Pholedrine

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title: "Pholedrine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["abandoned-drugs", "antihypotensive-agents", "human-drug-metabolites", "methamphetamines", "norepinephrine-dopamine-releasing-agents", "ophthalmology-drugs", "4-hydroxyphenyl-compounds", "recreational-drug-metabolites", "sympathomimetics"] description: "Chemical compound" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Pholedrine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 455126459 | IUPAC_name = 4-[2-(Methylamino)propyl]phenol | image = Pholedrine2D.svg | image_class = skin-invert-image | width = 225px

| tradename = Paredrinol, Presoitan, Pulsotyl, Veritain, Veritol | pregnancy_category = | legal_status = | routes_of_administration = Topical (ocular)

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 370-14-9 | PubChem = 4655 | UNII_Ref = | UNII = AY28O44JGD | KEGG_Ref = | KEGG = D08370 | ChEBI = 134798 | ChEMBL = 2008672 | ChemSpiderID_Ref = | ChemSpiderID = 4494 | DrugBank = DBMET00735 | synonyms = 4-Hydroxy-N-methylamphetamine; 4-HMA; 4-Hydroxymethamphetamine; para-Hydroxymethamphetamine; PHMA; Hydroxymethamphetamine

| C=10 | H=15 | N=1 | O=1 | SMILES = Oc1ccc(cc1)CC(NC)C | StdInChI_Ref = | StdInChI = 1S/C10H15NO/c1-8(11-2)7-9-3-5-10(12)6-4-9/h3-6,8,11-12H,7H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = SBUQZKJEOOQSBV-UHFFFAOYSA-N

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. It can be used to diagnose Horner's syndrome.

In 2004, it remained marketed only in Germany.

Pharmacology

Pharmacodynamics

Pholedrine is described as a sympathomimetic, antihypotensive, and ephedrine-like agent.

Chemistry

Pholedrine, also known as 4-hydroxy-N-methylamphetamine, is a substituted phenethylamine and amphetamine derivative. 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.

The predicted log P of pholedrine ranges from 1.12 to 1.7.

History

Pholedrine was synthesized by 1951.

Society and culture

Names

Pholedrine is the generic name of the drug and its , , and , while foledrina is its . The drug has been sold under brand names including Pholedrin Liquidum, Pholedrin-Longo-Isis, Presoitan, Veritain, and Veritol among others.

Other drugs

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

References

References

1. Schweizerischer Apotheker-Verein. (2004). "Index Nominum: International Drug Directory". Medpharm Scientific Publishers.
2. "Pholedrine". National Library of Medicine.
3. (February 1995). "Pholedrine: a substitute for hydroxyamphetamine as a diagnostic eyedrop test in Horner's syndrome". Journal of Neurology, Neurosurgery, and Psychiatry.
4. "Metabolite 4-hydroxymethamphetamine".
5. (21 July 2022). "Pholedrine".
6. (2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer US.
7. (2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Netherlands.

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