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 |
---|---|---|
Central interactions between dihydropyridines and cholinergic systems in the control of blood pressure in rat. | 1987 Dec 1 |
|
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 |
|
Bupivacaine inhibits baroreflex control of heart rate in conscious rats. | 2000 Jan |
|
Cardiovascular effects of hypocretin-1 in nucleus of the solitary tract. | 2003 Apr |
|
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 |
|
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 |
|
The analgesic effect of crotoxin on neuropathic pain is mediated by central muscarinic receptors and 5-lipoxygenase-derived mediators. | 2008 Dec |
|
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 |
|
Ghrelin infused into the portal vein inhibits glucose-stimulated insulin secretion in Wistar rats. | 2008 Jul |
|
Final answer: ghrelin can suppress insulin secretion in humans, but is it clinically relevant? | 2010 Nov |
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
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Record UNII |
80719I460H
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
A03BB02
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WHO-VATC |
QA03BB02
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80719I460H
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DTXSID5046932
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100000176330
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C006649
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31610-87-4
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DB13833
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4660
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METHYLATROPINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |