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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

Methylatropine (methylatroponium) is a belladonna derivative. In 1902 the Bayer Company introduced atropine methonitrate, a quaternary ammonium salt of atropine (Eumydrin), as a mydriatic for dilation of the pupil during ophthalmic examination. Due to its highly polar nature it penetrates less readily into the central nervous system than atropine and was therefore introduced for relieving pyloric spasms in infants. Atropine methyl nitrate is a muscarinic acetylcholine receptor antagonist that does not cross the blood-brain barrier. Atropine methyl nitrate has been used for its peripheral muscarinic effects (targeting the bladder, respiratory tract, and to block parasympathetic signaling to the heart, among others) and to separate central from peripheral nervous system effects, or to protect against peripheral side effects when using muscarinics that do cross the blood brain barrier.

CNS Activity

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

Originator

Sources: https://www.ncbi.nlm.nih.gov/pubmed/18799813Helgolaender Wissenschaftliche Meeresuntersuchungen (1966), 14, (1-2), 583-90.
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
Effects of atropine sulfate, methylatropine nitrate (metropine) and homatropine hydrobromide on adult human eyes.
1946 Sep
Clinical pertussis treated with methyl atropine nitrate (eumydrin).
1950 Oct 7
Ganglionic blocking action of atropine and methylatropine.
1953 Dec
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
Urethane inhibits cardiovascular responses mediated by the stimulation of alpha-2 adrenoceptors in the rat.
1982 Nov
Apparent reduction in baroreflex sensitivity to adenosine in conscious dogs.
1985 Sep
Bupivacaine inhibits baroreflex control of heart rate in conscious rats.
2000 Jan
Inhibition of [18F]FP-TZTP binding by loading doses of muscarinic agonists P-TZTP or FP-TZTP in vivo is not due to agonist-induced reduction in cerebral blood flow.
2003 Nov
Pharmacologic evidence for a parasympathetic role in seizure-induced neurocardiac regulatory abnormalities.
2004 Feb
Effects of angiotensin II on autonomic components of nasopharyngeal stimulation in male conscious rabbits.
2005 May
Facilitation of cardiac vagal activity by CRF-R1 antagonists during swim stress in rats.
2006 Dec
Cardiovascular responses produced by central injection of hydrogen peroxide in conscious rats.
2006 Dec 11
Sympathetic and parasympathetic component of bradycardia triggered by stimulation of NTS P2X receptors.
2006 Feb
The analgesic effect of crotoxin on neuropathic pain is mediated by central muscarinic receptors and 5-lipoxygenase-derived mediators.
2008 Dec
Ghrelin infused into the portal vein inhibits glucose-stimulated insulin secretion in Wistar rats.
2008 Jul
Xenin-25 potentiates glucose-dependent insulinotropic polypeptide action via a novel cholinergic relay mechanism.
2010 Jun 25
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.
Pyloric stenosis: The first dose was usually 0.5-1 ml (0.05-0.1 mgm. per dose), increasing by 0.5 ml at each feed till a dose of 2-3 ml, six times daily, was reached, i.e. 1.2-1.8 mgm. in twenty-four hours.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:51:55 UTC 2023
Edited
by admin
on Sat Dec 16 01:51:55 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 Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
WHO-VATC QA03BB02
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
Code System Code Type Description
FDA UNII
80719I460H
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046932
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
SMS_ID
100000176330
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
MESH
C006649
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
CAS
31610-87-4
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
DRUG BANK
DB13833
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
DRUG CENTRAL
4660
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 UTC 2023
PRIMARY
WIKIPEDIA
METHYLATROPINE
Created by admin on Sat Dec 16 01:51:56 UTC 2023 , Edited by admin on Sat Dec 16 01:51:56 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