Pholedrine

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]

Pholedrine

Clinical data
Trade names	Paredrinol, Presoitan, Pulsotyl, Veritain, Veritol
Other names	4-Hydroxy-N-methylamphetamine; 4-HMA; 4-Hydroxymethamphetamine; para-Hydroxymethamphetamine; PHMA; Hydroxymethamphetamine
Routes of administration	Topical (ocular)
Identifiers
IUPAC name 4-[2-(Methylamino)propyl]phenol
CAS Number	370-14-9 Y
PubChem CID	4655
DrugBank	DBMET00735
ChemSpider	4494 Y
UNII	AY28O44JGD
KEGG	D08370 Y
ChEBI	CHEBI:134798
ChEMBL	ChEMBL2008672
CompTox Dashboard (EPA)	DTXSID70861908
ECHA InfoCard	100.006.114
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc1ccc(cc1)CC(NC)C
InChI 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)

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.