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Pholedrine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.006.114Edit 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 as4-hydroxy-N-methylamphetamine and sold under the brand namesParedrinol,Pulsotyl, andVeritol among others, is asympathomimeticdrug used intopicaleye drops todilate the pupil.[1][2][3] It can be used to diagnoseHorner's syndrome.[3]

In 2004, it remained marketed only inGermany.[1]

Pharmacology

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Pharmacodynamics

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Pholedrine is described as asympathomimetic,antihypotensive, andephedrine-like agent.[4][1][5]

Chemistry

[edit]

Pholedrine, also known as 4-hydroxy-N-methylamphetamine, is asubstituted phenethylamine andamphetaminederivative.[4][1] It isstructurally related tomethamphetamine (N-methylamphetamine),norpholedrine (4-hydroxyamphetamine),oxilofrine (4,β-dihydroxy-N-methylamphetamine), andtyramine (4-hydroxyphenethylamine).

It is usedpharmaceutically as thesulfatesalt.[1][4]

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

History

[edit]

Pholedrine wassynthesized by 1951.[4]

Society and culture

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Names

[edit]

Pholedrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,BANTooltip British Approved Name, andDCFTooltip Dénomination Commune Française, whilefoledrina is itsDCITTooltip Denominazione Comune Italiana.[4][1][5] The drug has been sold under brand names includingPholedrin Liquidum,Pholedrin-Longo-Isis,Presoitan,Veritain, andVeritol among others.[4][1]

Other drugs

[edit]

Pholedrine (4-hydroxymethamphetamine) is also a majormetabolite ofmethamphetamine.

References

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  1. ^abcdefgSchweizerischer Apotheker-Verein (2004).Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 969.ISBN 978-3-88763-101-7. Retrieved30 August 2024.
  2. ^ab"Pholedrine". National Library of Medicine. Retrieved24 June 2023.
  3. ^abBates 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. ^abcdefElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 794.ISBN 978-1-4757-2085-3. Retrieved30 August 2024.
  5. ^abMorton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 219.ISBN 978-94-011-4439-1. Retrieved30 August 2024.
  6. ^"Metabolite 4-hydroxymethamphetamine".DrugBank Online. Retrieved30 August 2024.
  7. ^"Pholedrine".ChemSpider. 21 July 2022. Retrieved30 August 2024.
Enantiomers
Neuropharmacology
Biomolecular targets
Inhibited transporters
Health
History and culture
Law
Ethnicity and nationality
Anticholinergics/antimuscarinics
Sympathomimetics
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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