Details
Stereochemistry | EPIMERIC |
Molecular Formula | C18H26NO3.NO3 |
Molecular Weight | 366.4088 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+]([O-])=O.C[N+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3
InChI
InChIKey=NEDVJZNVOSNSHF-KUMOIWDRSA-N
InChI=1S/C18H26NO3.NO3/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;2-1(3)4/h3-7,14-17,20H,8-12H2,1-2H3;/q+1;-1/t14-,15+,16+,17?;
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 |
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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 |
|
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 |
|
Excess tachycardia: heart rate after antimuscarinic agents in conscious dogs. | 1984 Feb |
|
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 |
|
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 |
|
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 |
|
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 |
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The bradycardic and hypotensive responses to serotonin are reduced by activation of GABAA receptors in the nucleus tractus solitarius of awake rats. | 2005 Jul |
|
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 |
|
The analgesic effect of crotoxin on neuropathic pain is mediated by central muscarinic receptors and 5-lipoxygenase-derived mediators. | 2008 Dec |
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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 |
|
Modulation of heart rate variability during severe hemorrhage at different rates in conscious rats. | 2009 Oct 5 |
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
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SUB12156MIG
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436
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m2136
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C174866
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759122
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DTXSID0045543
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200-156-1
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100000079567
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C006649
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52-88-0
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Q48D9J47K2
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CHEMBL1187724
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ACTIVE MOIETY
SUBSTANCE RECORD