P-Hydroxyamfetamine

Hydroxyamfetamine
INN: hydroxyamfetamine
Clinical data

Trade names	Hydroxyamfetamine, Paredrine
Synonyms	hydroxyamphetamine (USAN US)
Routes of administration	Eye drops
ATC code	None
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 4-(2-aminopropyl)phenol
CAS Number	1518-86-1^Y
PubChem CID	3651
ChemSpider	3525^Y
ChEMBL	CHEMBL1546^Y
Chemical and physical data
Formula	C₉H₁₃NO
Molar mass	151.206 g/mol
3D model (JSmol)	Interactive image
SMILES Oc1ccc(cc1)CC(N)C
InChI InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3^Y Key:GIKNHHRFLCDOEU-UHFFFAOYSA-N^Y

4-Hydroxyamphetamine (4HA), also known as hydroxyamfetamine, hydroxyamphetamine, oxamphetamine, norpholedrine, para-hydroxyamphetamine, and α-methyltyramine, is a drug that stimulates the sympathetic nervous system.

It is used medically in eye drops to dilate the pupil (a process called mydriasis), so that the back of the eye can be examined. It is also a major metabolite of amphetamine and certain substituted amphetamines.

4-Hydroxyamphetamine is used in eye drops to dilate the pupil (a process called mydriasis) so that the back of the eye can be examined. This is a diagnostic test for Horner's Syndrome. Patients with Horner’s syndrome exhibit anisocoria brought about by lesions on the nerves that connect to the nasociliary branch of the ophthalmic nerve. Application of 4-hydroxyamphetamine to the eye can indicate whether the lesion is preganglionic or postganglionic based on the pupil’s response. If the pupil dilates, the lesion is preganglionic. If the pupil does not dilate, the lesion is postganglionic.

4-hydroxyamphetamine has some limitations to its use as a diagnostic tool. If it is intended as an immediate follow up to another mydriatic drug (cocaine or apraclonidine), then the patient must wait anywhere from a day to a week before 4-hydroxyamphetamine can be administered. It also has the tendency to falsely localize lesions. False localization can arise in cases of acute onset; in cases where a postganglionic lesion is present, but the nerve still responds to residual norepinephrine; or in cases in which unrelated nerve damage masks the presence of a preganglionic lesion.

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