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

Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO
Molecular Weight 165.2322
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOLEDRINE

SMILES

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

InChI

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

HIDE SMILES / InChI

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
Interactions of amphetamine analogs with human liver CYP2D6.
1997 Jun 1
Urinary excretion of the main metabolites of methamphetamine, including p-hydroxymethamphetamine-sulfate and p-hydroxymethamphetamine-glucuronide, in humans and rats.
2006 Feb-Mar
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:38:03 GMT 2023
Edited
by admin
on Fri Dec 15 16:38:03 GMT 2023
Record UNII
AY28O44JGD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOLEDRINE
INN   MI   WHO-DD  
INN  
Official Name English
PRESSITAN
Brand Name English
PHOLEDRINE [MI]
Common Name English
(±)-1-(4-HYDROXYPHENYL)-N-METHYL-2-AMINOPROPANE
Systematic Name English
KNOLL-H75
Code English
P-HYDROXY-N,.ALPHA.-DIMETHYLPHENETHYLAMINE
Common Name English
ISODRIN (SYMPATHOMIMETIC)
Common Name English
P-HYDROXYMETHAMPHETAMINE, (±)-
Common Name English
4-HYDROXY-N-METHYLAMPHETAMINE
Systematic Name English
PHENOL, 4-(2-(METHYLAMINO)PROPYL)-
Systematic Name English
Pholedrine [WHO-DD]
Common Name English
.BETA.-(P-HYDROXYPHENYL)ISOPROPYLMETHYLAMINE
Common Name English
PHENOL, P-(2-(METHYLAMINO)PROPYL)-
Common Name English
4-HYDROXYMETHAMPHETAMINE
Common Name English
ISODRINE
Common Name English
P-HYDROXY-N-METHYLAMPHETAMINE
Common Name English
PULSOTYL
Brand Name English
RACEMIC PHOLEDRINE
Common Name English
(±)-PHOLEDRINE
Common Name English
VERITOL
Common Name English
.ALPHA.-(P-HYDROXYPHENYL)-.BETA.-METHYLAMINOPROPANE
Common Name English
P-(2-METHYLAMINOPROPYL)PHENOL
Common Name English
OH-MA
Common Name English
pholedrine [INN]
Common Name English
4-(2-(METHYLAMINO)PROPYL)PHENOL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
Code System Code Type Description
EVMPD
SUB09796MIG
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
WIKIPEDIA
PHOLEDRINE
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
MESH
C005877
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
FDA UNII
AY28O44JGD
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
MERCK INDEX
m8712
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY Merck Index
INN
4190
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
PUBCHEM
4655
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
SMS_ID
100000082448
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
NCI_THESAURUS
C73067
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
CAS
370-14-9
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-725-0
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
RXCUI
33432
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2008672
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID70861908
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
DRUG CENTRAL
3463
Created by admin on Fri Dec 15 16:38:03 GMT 2023 , Edited by admin on Fri Dec 15 16:38:03 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
MAJOR
Related Record Type Details
ACTIVE MOIETY