U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO.ClH
Molecular Weight 201.693
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOLEDRINE HYDROCHLORIDE

SMILES

Cl.CNC(C)CC1=CC=C(O)C=C1

InChI

InChIKey=APSKAFWNZDJCNR-UHFFFAOYSA-N
InChI=1S/C10H15NO.ClH/c1-8(11-2)7-9-3-5-10(12)6-4-9;/h3-6,8,11-12H,7H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H15NO
Molecular Weight 165.2322
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Pholedrine is a hydroxymethylamphetamine. It is a sympathimimetric drug of low toxicity, which is of great value in conditions of hypotonia, collapse, and circulatory depression. Pholedrine was reported on in 1937 by several investigators, who described its vasopressor action in animals as more potent than that of ephedrine. The drug is grouped with hydroxyamphetamine because of its similarity in structure and hemodynamic pattern. Pholedrine, in small doses, potentiates epinephrine, but in large doses blocks its pressor effect. Pholedrine applied as eye-drops produces mydriasis that is greatly attenuated by guanethidine pretreatment and diminished in patients with postganglionic sympathetic nerve lesions. It might be used to diagnose Horner's syndrome.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.7 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLEDRINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Urinary excretion of the main metabolites of methamphetamine, including p-hydroxymethamphetamine-sulfate and p-hydroxymethamphetamine-glucuronide, in humans and rats.
2006-05-17
Direct determination of p-hydroxymethamphetamine glucuronide in human urine by high-performance liquid chromatography.
2006-04
LC-MS/MS analysis of pholedrine in a fatal intoxication case.
2003-04-23
Interactions of amphetamine analogs with human liver CYP2D6.
1997-06-01
Simultaneous determination of methamphetamine and its metabolites in monkey urine by gas chromatography/mass spectrometry with selected ion monitoring.
1989-03-01
Substance Class Chemical
Created
by admin
on Wed Apr 02 13:26:33 GMT 2025
Edited
by admin
on Wed Apr 02 13:26:33 GMT 2025
Record UNII
W5PL3LUP2K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOLEDRINE HYDROCHLORIDE
Common Name English
PAREDRINOL HYDROCHLORIDE
Preferred Name English
PHENOL, 4-(2-(METHYLAMINO)PROPYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
4-HYDROXYMETHAMPHETAMINE (HYDROCHLORIDE)
Common Name English
PHENOL, 4-(2-(METHYLAMINO)PROPYL)-, HYDROCHLORIDE
Systematic Name English
PHENOL, P-(2-(METHYLAMINO)PROPYL)-, HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
W5PL3LUP2K
Created by admin on Wed Apr 02 13:26:33 GMT 2025 , Edited by admin on Wed Apr 02 13:26:33 GMT 2025
PRIMARY
PUBCHEM
129704879
Created by admin on Wed Apr 02 13:26:33 GMT 2025 , Edited by admin on Wed Apr 02 13:26:33 GMT 2025
PRIMARY
CAS
877-86-1
Created by admin on Wed Apr 02 13:26:33 GMT 2025 , Edited by admin on Wed Apr 02 13:26:33 GMT 2025
PRIMARY