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

Details

Stereochemistry EPIMERIC
Molecular Formula C18H26NO3.Br
Molecular Weight 384.308
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLATROPINE BROMIDE

SMILES

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

InChI

InChIKey=XMLNCADGRIEXPK-KUMOIWDRSA-M
InChI=1S/C18H26NO3.BrH/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;1H/q+1;/p-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

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Quantification of tremor in rats induced by physostigmine.
1981
Cardiovascular responses to intracisternal administration of nicotine in rats.
1981 Jun
Changes in blood-brain barrier permeability to drugs in decompressed rats.
1982 Sep
Drugs for Parkinson's disease reduce tremor induced by physostigmine.
1983 Jul
[Effects of oxybutynin on the cardiovascular system in dogs].
1984 Oct
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
The bradycardic and hypotensive responses to serotonin are reduced by activation of GABAA receptors in the nucleus tractus solitarius of awake rats.
2005 Jul
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
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
Acute induction of epileptiform discharges by pilocarpine in the in vitro isolated guinea-pig brain requires enhancement of blood-brain barrier permeability.
2008 Jan 2
Effect of ghrelin on glucose-insulin homeostasis: therapeutic implications.
2010
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 Fri Dec 15 17:06:12 UTC 2023
Edited
by admin
on Fri Dec 15 17:06:12 UTC 2023
Record UNII
63IFT0IX9N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLATROPINE BROMIDE
EP  
Common Name English
ATROPINE METHYL BROMIDE
Common Name English
ATROPINE METHYLBROMIDE [MI]
Common Name English
NSC-61810
Code English
ATROPINE METHYLBROMIDE [JAN]
Common Name English
ATROPINE METHOBROMIDE [MART.]
Common Name English
ATROPINE METHOBROMIDE
MART.  
Common Name English
Atropine methylbromide [WHO-DD]
Common Name English
3.ALPHA.-HYDROXY-8-METHYL-1AH,5AH-TROPANIUM BROMIDE
Common Name English
ATROPINE METHYLBROMIDE
JAN   MI   WHO-DD  
Common Name English
TROPIN
Brand Name English
METHYLATROPINE BROMIDE [EP IMPURITY]
Common Name English
Code System Code Type Description
CAS
2870-71-5
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1187724
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
EVMPD
SUB00623MIG
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
MERCK INDEX
m2136
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID2045103
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
220-700-1
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
SMS_ID
100000085344
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
FDA UNII
63IFT0IX9N
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
MESH
C006649
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
NSC
61810
Created by admin on Fri Dec 15 17:06:12 UTC 2023 , Edited by admin on Fri Dec 15 17:06:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE