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
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?
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19523969http://www.sigmaaldrich.com/catalog/product/sigma/sml0732?lang=es®ion=ES
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
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 mg multiple, oral (total) |
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) Sources: Hypotonic urinary bladder (1 patient) |
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... |
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... |
16 mg multiple, oral (total) Highest studied dose |
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) Sources: Hypertonia (1 patient) Dilated pupils (1 patient) |
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
AE | Significance | Dose | Population |
---|---|---|---|
Hypotonic urinary bladder | 1 patient | 0.8 mg multiple, oral (total) |
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) |
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 |
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 |
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 |
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
Title | Date | PubMed |
---|---|---|
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 |
|
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 |
|
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 |
|
Participation of cholinergic pathways in sinoaortic denervated rats. | 1985 |
|
Apparent reduction in baroreflex sensitivity to adenosine in conscious dogs. | 1985 Sep |
|
Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin. | 1986 Feb |
|
The role of cholinergic systems in the expression of morphine withdrawal. | 1996 Jun |
|
Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. | 2003 Dec |
|
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 |
|
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 |
|
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 |
|
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 |
|
Modulation of heart rate variability during severe hemorrhage at different rates in conscious rats. | 2009 Oct 5 |
|
Post-exposure treatment with nasal atropine methyl bromide protects against microinstillation inhalation exposure to sarin in guinea pigs. | 2009 Sep 15 |
|
Effect of ghrelin on glucose-insulin homeostasis: therapeutic implications. | 2010 |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21032188
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:51:55 GMT 2023
by
admin
on
Sat Dec 16 01:51:55 GMT 2023
|
Record UNII |
80719I460H
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
A03BB02
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
||
|
WHO-VATC |
QA03BB02
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
80719I460H
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
DTXSID5046932
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
100000176330
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
C006649
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
31610-87-4
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
DB13833
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
4660
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 2023
|
PRIMARY | |||
|
METHYLATROPINE
Created by
admin on Sat Dec 16 01:51:56 GMT 2023 , Edited by admin on Sat Dec 16 01:51:56 GMT 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 |