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
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
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 |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/13558159https://www.ncbi.nlm.nih.gov/pubmed/6076581 | https://www.ncbi.nlm.nih.gov/pubmed/2874970 | https://www.ncbi.nlm.nih.gov/pubmed/13558159 | https://www.ncbi.nlm.nih.gov/pubmed/23981808Curator's Comment: description was created based on several sources, including, http://toxcenter.org/stoff-infos/l/levopropylhexedrin.pdf
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13558159https://www.ncbi.nlm.nih.gov/pubmed/6076581 | https://www.ncbi.nlm.nih.gov/pubmed/2874970 | https://www.ncbi.nlm.nih.gov/pubmed/13558159 | https://www.ncbi.nlm.nih.gov/pubmed/23981808
Curator's Comment: description was created based on several sources, including, http://toxcenter.org/stoff-infos/l/levopropylhexedrin.pdf
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.
CNS Activity
Sources: http://toxcenter.org/stoff-infos/l/levopropylhexedrin.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/6076581 | https://www.ncbi.nlm.nih.gov/pubmed/2874970 | https://www.researchgate.net/publication/232245051_Propylhexedrine_A_Vintage_Drug_of_Abuse_Rediscovered | https://www.ncbi.nlm.nih.gov/pubmed/2874970
Curator's Comment: The levorotatory isomer is the more active releaser of nor-epinephrine and dopamine in the central nervous system
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5857 Sources: https://www.drugbank.ca/drugs/DB06714 |
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Target ID: CHEMBL2095203 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Eventin Approved UseAppetite depressant |
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Primary | Benzedrex Approved UseSelf-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other allergies. |
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Primary | Benzedrex Approved UseSelf-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other allergies. |
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Primary | Maliasin Approved UseBarbexoclone (Maliasin®) is an antiepileptic drug, which has been found to be effective in the treatment of epilepsy. Launch Date1983 |
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Curative | Eventin Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6139756/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6139756/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6139756/ |
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
Dose | Population | Adverse 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) Sources: Death (grade 5) |
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) Sources: Death (grade 5) |
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) Sources: Death (grade 5) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
[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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:06:06 GMT 2023
by
admin
on
Fri Dec 15 16:06:06 GMT 2023
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Record UNII |
4R3L4TYV09
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Record Status |
Validated (UNII)
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Record Version |
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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
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Code System | Code | Type | Description | ||
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Levopropylhexedrine
Created by
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PRIMARY | |||
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53690-40-7
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SUPERSEDED | |||
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50453-50-4
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SUPERSEDED | |||
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100000082282
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PRIMARY | |||
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DTXSID801024267
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PRIMARY | |||
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C83883
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PRIMARY | |||
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4R3L4TYV09
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PRIMARY | |||
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m9242
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PRIMARY | Merck Index | ||
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CHEMBL2105014
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PRIMARY | |||
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228-245-0
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PRIMARY | |||
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42870-71-3
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SUPERSEDED | |||
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SUB08487MIG
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PRIMARY | |||
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6192-97-8
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PRIMARY | |||
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4279
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71197
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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RACEMATE -> ENANTIOMER |
Related Record | Type | Details | ||
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ACTIVE MOIETY |