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

Details

Stereochemistry EPIMERIC
Molecular Formula C18H26NO3
Molecular Weight 304.4039
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of METHYLATROPINIUM

SMILES

C[N+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3

InChI

InChIKey=PIPAJLPNWZMYQA-KNCRFDSUSA-N
InChI=1S/C18H26NO3/c1-19(2)14-8-9-15(19)11-16(10-14)22-18(21)17(12-20)13-6-4-3-5-7-13/h3-7,14-17,20H,8-12H2,1-2H3/q+1/t14-,15+,16+,17?

HIDE SMILES / InChI

Molecular Formula C18H25NO3
Molecular Weight 303.396
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

In 1902, the Bayer company introduced first quaternary salt of atropine, methylatropine (nitrate salt), under the name of Eumydrin, as a mydriatic. Because of its highly polar nature it penetrated less readily into the central nervous system than did atropine; hence it was introduced for relieving pyloric spasm in infants. The drug has the same action as atropine and antagonizes muscarinic acetylcholine receptors.

CNS Activity

Curator's Comment: Atropine methyl nitrate is a muscarinic acetylcholine receptor antagonist that does not cross the blood brain barrier.

Originator

Sources: Helgolaender Wissenschaftliche Meeresuntersuchungen (1966), 14, (1-2), 583-90.https://www.ncbi.nlm.nih.gov/pubmed/18799813
Curator's Comment: # Bayer

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Diagnostic
Eumydrin

Approved Use

Unknown

Launch Date

-2.14591681E12
Palliative
Eumydrin

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
0.8 mg multiple, oral (total)
Dose: 0.8 mg
Route: oral
Route: multiple
Dose: 0.8 mg
Sources:
unhealthy, 1 week
n = 1
Health Status: unhealthy
Age Group: 1 week
Population Size: 1
Sources:
Other AEs: Paralytic ileus, Hypotonic urinary bladder...
Other AEs:
Paralytic ileus (1 patient)
Hypotonic urinary bladder (1 patient)
Sources:
0.4 mg 6 times / day multiple, oral
Dose: 0.4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 0.4 mg, 6 times / day
Sources:
unhealthy, 2 month
n = 1
Health Status: unhealthy
Age Group: 2 month
Sex: M
Population Size: 1
Sources:
Other AEs: Dilated pupils, Fever...
Other AEs:
Dilated pupils
Fever
Sources:
2.5 mL 1 times / day multiple, oral
Dose: 2.5 mL, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mL, 1 times / day
Sources:
unhealthy, 37 days
n = 1
Health Status: unhealthy
Age Group: 37 days
Sex: M
Population Size: 1
Sources:
Other AEs: Paralytic ileus...
Other AEs:
Paralytic ileus (grade 5)
Sources:
16 mg multiple, oral (total)
Highest studied dose
Dose: 16 mg
Route: oral
Route: multiple
Dose: 16 mg
Sources:
unhealthy, 7 weeks
n = 1
Health Status: unhealthy
Age Group: 7 weeks
Population Size: 1
Sources:
Other AEs: Irritable, Hypertonia...
Other AEs:
Irritable (1 patient)
Hypertonia (1 patient)
Dilated pupils (1 patient)
Sources:
0.1 mg 1 times / day multiple, oral (starting)
Dose: 0.1 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.1 mg, 1 times / day
Sources:
unhealthy, babies
n = 15
Health Status: unhealthy
Age Group: babies
Population Size: 15
Sources:
Disc. AE: Abdominal distension...
AEs leading to
discontinuation/dose reduction:
Abdominal distension
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypotonic urinary bladder 1 patient
0.8 mg multiple, oral (total)
Dose: 0.8 mg
Route: oral
Route: multiple
Dose: 0.8 mg
Sources:
unhealthy, 1 week
n = 1
Health Status: unhealthy
Age Group: 1 week
Population Size: 1
Sources:
Paralytic ileus 1 patient
0.8 mg multiple, oral (total)
Dose: 0.8 mg
Route: oral
Route: multiple
Dose: 0.8 mg
Sources:
unhealthy, 1 week
n = 1
Health Status: unhealthy
Age Group: 1 week
Population Size: 1
Sources:
Dilated pupils
0.4 mg 6 times / day multiple, oral
Dose: 0.4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 0.4 mg, 6 times / day
Sources:
unhealthy, 2 month
n = 1
Health Status: unhealthy
Age Group: 2 month
Sex: M
Population Size: 1
Sources:
Fever
0.4 mg 6 times / day multiple, oral
Dose: 0.4 mg, 6 times / day
Route: oral
Route: multiple
Dose: 0.4 mg, 6 times / day
Sources:
unhealthy, 2 month
n = 1
Health Status: unhealthy
Age Group: 2 month
Sex: M
Population Size: 1
Sources:
Paralytic ileus grade 5
2.5 mL 1 times / day multiple, oral
Dose: 2.5 mL, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mL, 1 times / day
Sources:
unhealthy, 37 days
n = 1
Health Status: unhealthy
Age Group: 37 days
Sex: M
Population Size: 1
Sources:
Dilated pupils 1 patient
16 mg multiple, oral (total)
Highest studied dose
Dose: 16 mg
Route: oral
Route: multiple
Dose: 16 mg
Sources:
unhealthy, 7 weeks
n = 1
Health Status: unhealthy
Age Group: 7 weeks
Population Size: 1
Sources:
Hypertonia 1 patient
16 mg multiple, oral (total)
Highest studied dose
Dose: 16 mg
Route: oral
Route: multiple
Dose: 16 mg
Sources:
unhealthy, 7 weeks
n = 1
Health Status: unhealthy
Age Group: 7 weeks
Population Size: 1
Sources:
Irritable 1 patient
16 mg multiple, oral (total)
Highest studied dose
Dose: 16 mg
Route: oral
Route: multiple
Dose: 16 mg
Sources:
unhealthy, 7 weeks
n = 1
Health Status: unhealthy
Age Group: 7 weeks
Population Size: 1
Sources:
Abdominal distension Disc. AE
0.1 mg 1 times / day multiple, oral (starting)
Dose: 0.1 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.1 mg, 1 times / day
Sources:
unhealthy, babies
n = 15
Health Status: unhealthy
Age Group: babies
Population Size: 15
Sources:
PubMed

PubMed

TitleDatePubMed
The difference in the effects of tertiary and quaternary ammonium bases (proserine, serine, methylatropine and atropine) depending on the method of administration.
1962 Mar
Analysis of cardiac chronotropic responses to diazepam and bromazepam in conscious trained dogs.
1976 Feb
Influence of several anesthetic agents on the effect of delta9-tetrahydrocannabinol on the heart rate and blood pressure of the mongrel dog.
1977 Jul 1
Effect of thyrotropin-releasing hormone (TRH) on local cerebral glucose utilization, by the autoradiographic 2-deoxy[14C]glucose method, in conscious and pentobarbitalized rats.
1980 Oct
Quantification of tremor in rats induced by physostigmine.
1981
Cardiovascular responses to intracisternal administration of nicotine in rats.
1981 Jun
Urethane inhibits cardiovascular responses mediated by the stimulation of alpha-2 adrenoceptors in the rat.
1982 Nov
Drugs for Parkinson's disease reduce tremor induced by physostigmine.
1983 Jul
Pharmacological, hemodynamic and autonomic nervous system mechanisms responsible for the blood pressure and heart rate lowering effects of pergolide in rats.
1984 Mar
[Effects of oxybutynin on the cardiovascular system in dogs].
1984 Oct
Apparent reduction in baroreflex sensitivity to adenosine in conscious dogs.
1985 Sep
L-glutamate stimulation of the zona incerta in the rat decreases heart rate and blood pressure.
1988 Aug 16
Endogenous gamma-aminobutyric acid (GABA) mediates ethanol inhibition of vagally mediated reflex bradycardia elicited from aortic baroreceptors.
1994 Feb
The role of cholinergic systems in the expression of morphine withdrawal.
1996 Jun
Central muscarinic receptors signal pilocarpine-induced salivation.
2003 Dec
Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate.
2003 Dec
Cardioacceleratory responses to hypocretin-1 injections into rostral ventromedial medulla.
2003 Nov 21
Dual effects of acupuncture on gastric motility in conscious rats.
2003 Oct
The bradycardic and hypotensive responses to serotonin are reduced by activation of GABAA receptors in the nucleus tractus solitarius of awake rats.
2005 Jul
Effects of angiotensin II on autonomic components of nasopharyngeal stimulation in male conscious rabbits.
2005 May
Effects of AV3V lesion on pilocarpine-induced pressor response and salivary gland vasodilation.
2005 Sep 7
Sympathetic and parasympathetic component of bradycardia triggered by stimulation of NTS P2X receptors.
2006 Feb
Medical countermeasure against respiratory toxicity and acute lung injury following inhalation exposure to chemical warfare nerve agent VX.
2007 Mar
Medullary pathways mediating the parasubthalamic nucleus depressor response.
2008 Apr
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: A drop of this solution placed on the surface of the tongue is rapidly absorbed and the treatment and absorption are not interfered with by the vomiting.
for children: to begin with 1 to 2 drops daily and gradually increase the dose if necessary until the vomiting becomes less severe.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 08:08:19 UTC 2023
Edited
by admin
on Thu Jul 06 08:08:19 UTC 2023
Record UNII
80719I460H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLATROPINIUM
Common Name English
8-AZONIABICYCLO(3.2.1)OCTANE, 3-(3-HYDROXY-1-OXO-2- PHENYLPROPOXY)-8,8-DIMETHYL-, (3-ENDO)-
Common Name English
METHYLATROPINE
WHO-DD  
Common Name English
8-AZONIABICYCLO(3.2.1)OCTANE, 3-(3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-8,8-DIMETHYL-, (3-ENDO)-
Common Name English
METHYLATROPINIUM ION
Common Name English
N-METHYLATROPINIUM
Code English
METHYLATROPINIUM CATION
Common Name English
(±)-N-METHYLATROPINE
Common Name English
HOMATROPINE METHYLBROMIDE IMPURITY E [EP IMPURITY]
Common Name English
Methylatropine [WHO-DD]
Common Name English
N-METHYLATROPINE
Common Name English
Classification Tree Code System Code
WHO-ATC A03BB02
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
WHO-VATC QA03BB02
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
Code System Code Type Description
FDA UNII
80719I460H
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046932
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
SMS_ID
100000176330
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
MESH
C006649
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
CAS
31610-87-4
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
DRUG BANK
DB13833
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
DRUG CENTRAL
4660
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
WIKIPEDIA
METHYLATROPINE
Created by admin on Thu Jul 06 08:08:19 UTC 2023 , Edited by admin on Thu Jul 06 08:08:19 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY