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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H21N
Molecular Weight 155.2804
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOPROPYLHEXEDRINE

SMILES

CN[C@@H](C)CC1CCCCC1

InChI

InChIKey=JCRIVQIOJSSCQD-VIFPVBQESA-N
InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3/t9-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H21N
Molecular Weight 155.2804
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Propylhexedrine Hydrochloride is an α-adrenergic sympathomimetic amine that acts as a local vasoconstrictor. It is the active ingredient in some over-the-counter nasal decongestants, typically by intravenous or oral delivery of the nasal decongestant. Propylhexedrine is known under the brand name Benzedrex. Propylhexedrine has also seen use in Europe as an appetite suppressant under the trade name Obesin and in the anticonvulsant preparation barbexaclone its S-isomer PROPYLHEXEDRINE HYDROCHLORIDE, (-)- (levopropylhexedrine or L-propylhexedrine) is bonded with phenobarbital for the purpose of offsetting the barbiturate-induced sedation. Levopropylhexedrine is also used as an anorectic under the brand name Eventin.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eventin

Approved Use

Appetite depressant
Primary
Benzedrex

Approved Use

Self-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other allergies.
Primary
Benzedrex

Approved Use

Self-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other allergies.
Primary
Maliasin

Approved Use

Barbexoclone (Maliasin®) is an antiepileptic drug, which has been found to be effective in the treatment of epilepsy.

Launch Date

1983
Curative
Eventin

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 μg/mL
66 mg/kg 1 times / day steady-state, oral
dose: 66 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PHENOBARBITAL
PROPYLHEXEDRINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.3 μg × h/mL
66 mg/kg 1 times / day steady-state, oral
dose: 66 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PHENOBARBITAL
PROPYLHEXEDRINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
66 mg/kg 1 times / day steady-state, oral
dose: 66 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PHENOBARBITAL
PROPYLHEXEDRINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 17 years
n = 1
Health Status: unknown
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 19 years
n = 1
Health Status: unknown
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 19 years
n = 1
Health Status: unknown
Age Group: 19 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 22 years
n = 1
Health Status: unknown
Age Group: 22 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death, Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 23 years
n = 1
Health Status: unknown
Age Group: 23 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 24 years
n = 1
Health Status: unknown
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 25 years
n = 1
Health Status: unknown
Age Group: 25 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
180 mg 1 times / day steady, oral
Studied dose
Dose: 180 mg, 1 times / day
Route: oral
Route: steady
Dose: 180 mg, 1 times / day
Sources:
healthy, 25-37 years
n = 7
Health Status: healthy
Age Group: 25-37 years
Sex: M
Population Size: 7
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 26 years
n = 1
Health Status: unknown
Age Group: 26 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 27 years
n = 1
Health Status: unknown
Age Group: 27 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death, Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 28 years
n = 1
Health Status: unknown
Age Group: 28 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 29 years
n = 1
Health Status: unknown
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Death, Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Death (grade 5)
Sources:
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 34 years
n = 1
Health Status: unknown
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 17 years
n = 1
Health Status: unknown
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 19 years
n = 1
Health Status: unknown
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 19 years
n = 1
Health Status: unknown
Age Group: 19 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 22 years
n = 1
Health Status: unknown
Age Group: 22 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 22 years
n = 1
Health Status: unknown
Age Group: 22 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 23 years
n = 1
Health Status: unknown
Age Group: 23 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 24 years
n = 1
Health Status: unknown
Age Group: 24 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 25 years
n = 1
Health Status: unknown
Age Group: 25 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 26 years
n = 1
Health Status: unknown
Age Group: 26 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 27 years
n = 1
Health Status: unknown
Age Group: 27 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 27 years
n = 1
Health Status: unknown
Age Group: 27 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 28 years
n = 1
Health Status: unknown
Age Group: 28 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 29 years
n = 1
Health Status: unknown
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 29 years
n = 1
Health Status: unknown
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Death grade 5
Disc. AE
250 mg single, intravenous
Abused dose
Dose: 250 mg
Route: intravenous
Route: single
Dose: 250 mg
Sources:
unknown, 34 years
n = 1
Health Status: unknown
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Therapeutic experiences with the appetite depressant eventin].
1958 Apr 5
A comparison of the anticonvulsant properties of l-propylhexedrine, phenobarbital and a salt-like complex of l-propylhexedrine and phenobarbital in mice and rats.
1967 Dec
[L-thyroxine propylhexedrine in the treatment of obesity. Crossed double blind study].
1974 May-Jun
Intravenous abuse of propylhexedrine.
1977 Jan
Intravenous prophylhexedrine (Benzedrex®) abuse and sudden death.
1979 Jul
Propylhexdrine.
1986 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:06:06 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:06 GMT 2023
Record UNII
4R3L4TYV09
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOPROPYLHEXEDRINE
INN   WHO-DD  
INN  
Official Name English
levopropylhexedrine [INN]
Common Name English
L-PROPYLHEXEDRINE
Common Name English
L-1-CYCLOHEXYL-2-METHYLAMINOPROPANE
Common Name English
Levopropylhexedrine [WHO-DD]
Common Name English
EVENTIN
Brand Name English
PROPYLHEXEDRINE L-FORM [MI]
Common Name English
(-)-N,.ALPHA.-DIMETHYLCYCLOHEXANEETHYLAMINE
Systematic Name English
PROPYLHEXEDRINE, (S)-
Common Name English
(-)-PROPYLHEXEDRINE
Common Name English
CYCLOHEXANEETHANAMINE, N,.ALPHA.-DIMETHYL-, (.ALPHA.S)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
Code System Code Type Description
WIKIPEDIA
Levopropylhexedrine
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
CAS
53690-40-7
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
SUPERSEDED
CAS
50453-50-4
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
SUPERSEDED
SMS_ID
100000082282
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID801024267
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
NCI_THESAURUS
C83883
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
FDA UNII
4R3L4TYV09
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
MERCK INDEX
m9242
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2105014
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
228-245-0
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
CAS
42870-71-3
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
SUPERSEDED
EVMPD
SUB08487MIG
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
CAS
6192-97-8
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
INN
4279
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
PUBCHEM
71197
Created by admin on Fri Dec 15 16:06:06 GMT 2023 , Edited by admin on Fri Dec 15 16:06:06 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
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ACTIVE MOIETY