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

Details

Stereochemistry RACEMIC
Molecular Formula C9H19N
Molecular Weight 141.2539
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOMETHEPTENE

SMILES

CNC(C)CCC=C(C)C

InChI

InChIKey=XVQUOJBERHHONY-UHFFFAOYSA-N
InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C9H19N
Molecular Weight 141.2539
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02290379 | https://www.ncbi.nlm.nih.gov/pubmed/22288671 | https://clinicaltrials.gov/ct2/show/NCT02706015 | https://www.drugbank.ca/drugs/DB06706

Isometheptene (usually as isometheptene mucate) is a sympathomimetic amine sometimes used in the treatment of migraines and tension headaches due to its vasoconstricting properties. Isometheptene's vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine. These compounds elicit smooth muscle activation leading to vasoconstriction by interacting with cell surface adrenergic receptors.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Neosaldina

Approved Use

Unknown
Primary
Neosaldina

Approved Use

Unknown
Primary
Neosaldina

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
120 mg 1 times / episode multiple, oral
Studied dose
Dose: 120 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 120 mg, 1 times / episode
Co-administed with::
dipyrone(1200 mg)
caffeine(120 mg)
Sources:
unhealthy, 18 to 65 years
n = 76
Health Status: unhealthy
Condition: primary headache
Age Group: 18 to 65 years
Sex: M+F
Population Size: 76
Sources:
Other AEs: Angioneurotic edema, Epigastralgia...
Other AEs:
Angioneurotic edema (grade 1, 1.3%)
Epigastralgia (grade 1, 1.3%)
Sources:
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Other AEs: Dizziness, Numbness...
Other AEs:
Dizziness (17.1%)
Numbness (5.7%)
Shortness of breath (2.8%)
Chills (2.8%)
Nausea (2.8%)
Drowsiness (2.8%)
Sources:
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Other AEs: Abdominal pain, Nausea...
Other AEs:
Abdominal pain (3.1%)
Nausea (3.1%)
Lightheadedness (6.1%)
Sleepiness (3.1%)
Dry mouth (1.5%)
Hot flashes (1.5%)
Palpitations (1.5%)
Enlarged thyroid (1.5%)
Confusion (1.5%)
Sources:
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Other AEs: Nausea, Vertigo...
Other AEs:
Nausea (40%)
Vertigo (8%)
Lump feeling in throat (8%)
Drowsiness (4%)
Tachycardia (4%)
Itching (4%)
Dry mouth (4%)
Weakness of limbs (4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Angioneurotic edema grade 1, 1.3%
120 mg 1 times / episode multiple, oral
Studied dose
Dose: 120 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 120 mg, 1 times / episode
Co-administed with::
dipyrone(1200 mg)
caffeine(120 mg)
Sources:
unhealthy, 18 to 65 years
n = 76
Health Status: unhealthy
Condition: primary headache
Age Group: 18 to 65 years
Sex: M+F
Population Size: 76
Sources:
Epigastralgia grade 1, 1.3%
120 mg 1 times / episode multiple, oral
Studied dose
Dose: 120 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 120 mg, 1 times / episode
Co-administed with::
dipyrone(1200 mg)
caffeine(120 mg)
Sources:
unhealthy, 18 to 65 years
n = 76
Health Status: unhealthy
Condition: primary headache
Age Group: 18 to 65 years
Sex: M+F
Population Size: 76
Sources:
Dizziness 17.1%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Chills 2.8%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Drowsiness 2.8%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Nausea 2.8%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Shortness of breath 2.8%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Numbness 5.7%
780 mg 1 times / episode multiple, oral
Studied dose
Dose: 780 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 780 mg, 1 times / episode
Sources:
unhealthy, mean age 33 years
n = 36
Health Status: unhealthy
Condition: migraine
Age Group: mean age 33 years
Sex: M+F
Population Size: 36
Sources:
Confusion 1.5%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Dry mouth 1.5%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Enlarged thyroid 1.5%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Hot flashes 1.5%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Palpitations 1.5%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Abdominal pain 3.1%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Nausea 3.1%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Sleepiness 3.1%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Lightheadedness 6.1%
65 mg 1 times / hour multiple, oral
Recommended
Dose: 65 mg, 1 times / hour
Route: oral
Route: multiple
Dose: 65 mg, 1 times / hour
Co-administed with::
dichloralphenazone(500 mg per 12 h)
acetaminophen(1625 mg per 12 h)
Sources:
unhealthy, mean age 40.9 years
n = 65
Health Status: unhealthy
Condition: migraine
Age Group: mean age 40.9 years
Sex: M+F
Population Size: 65
Sources:
Drowsiness 4%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Dry mouth 4%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Itching 4%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Tachycardia 4%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Weakness of limbs 4%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Nausea 40%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Lump feeling in throat 8%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
Vertigo 8%
325 mg 1 times / episode multiple, oral
Recommended
Dose: 325 mg, 1 times / episode
Route: oral
Route: multiple
Dose: 325 mg, 1 times / episode
Co-administed with::
acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months)
Sources:
unhealthy, mean age 49 years
n = 25
Health Status: unhealthy
Condition: migraine
Age Group: mean age 49 years
Sex: M+F
Population Size: 25
Sources:
PubMed

PubMed

TitleDatePubMed
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.
2001 Apr
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.
2001 Jul
Migraine: diagnosis, management, and new treatment options.
2002 Feb
Fixed drug combinations for the acute treatment of migraine : place in therapy.
2005
Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery.
2006 Dec
Time to pain freedom and onset of pain relief with rizatriptan 10 mg and prescription usual-care oral medications in the acute treatment of migraine headaches: a multicenter, prospective, open-label, two-attack, crossover study.
2006 Jun
Intracerebral hemorrhage in postpartum cerebral angiopathy associated with the use of isometheptene.
2006 Nov
Acute migraine: Current treatment and emerging therapies.
2007 Jun
Current and prospective pharmacological targets in relation to antimigraine action.
2008 Oct
Life threatening intracerebral hemorrhage with isometheptene mucate, dichlorophenazine and acetaminophen combination therapy.
2009 Nov
Rizatriptan for the acute treatment of migraine: Consistency, preference, satisfaction, and quality of life.
2009 Nov 3
Epidemiological analysis of doping offences in the professional tennis circuit.
2010 Dec 15
Patents

Patents

Sample Use Guides

Single dose 1 to 2 tablets/days, Daily Maximum Dose: 8 tablets (4 x 2 dragees). One tablet contains 30 mg of Isometheptene Mucate.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:00 UTC 2023
Edited
by admin
on Fri Dec 15 15:23:00 UTC 2023
Record UNII
Y7L24THH6T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOMETHEPTENE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ISOMETHEPTENE [MART.]
Common Name English
isometheptene [INN]
Common Name English
N,1,5-TRIMETHYL-4-HEXENYLAMINE
Systematic Name English
ISOMETHEPTENE [MI]
Common Name English
6-METHYLAMINO-2-METHYLHEPTENE
Systematic Name English
OCTIN
Brand Name English
4-HEXENYLAMINE, N,1,5-TRIMETHYL-
Systematic Name English
ISONYL
Brand Name English
2-METHYL-6-METHYLAMINO-2-HEPTENE
Systematic Name English
N,6-DIMETHYL-5-HEPTEN-2-AMINE
Systematic Name English
OCTANIL
Brand Name English
5-HEPTEN-2-AMINE, N,6-DIMETHYL-
Systematic Name English
Isometheptene [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 520
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
WHO-ATC A03AX10
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
WHO-VATC QA03AX10
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
Code System Code Type Description
INN
576
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
RXCUI
27946
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY RxNorm
PUBCHEM
22297
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
NCI_THESAURUS
C75929
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-959-6
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
CAS
65783-53-1
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
SUPERSEDED
DRUG BANK
DB06706
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
MERCK INDEX
m6501
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY Merck Index
EVMPD
SUB08324MIG
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL1697841
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
SMS_ID
100000082812
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
MESH
C008192
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023172
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
CAS
503-01-5
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
FDA UNII
Y7L24THH6T
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
DRUG CENTRAL
1496
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
WIKIPEDIA
Isometheptene
Created by admin on Fri Dec 15 15:23:00 UTC 2023 , Edited by admin on Fri Dec 15 15:23:00 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY