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 |
|
| Analysis of cardiac chronotropic responses to diazepam and bromazepam in conscious trained dogs. | 1976 Feb |
|
| 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 |
|
| Quantification of tremor in rats induced by physostigmine. | 1981 |
|
| Cardiovascular responses to intracisternal administration of nicotine in rats. | 1981 Jun |
|
| Urethane inhibits cardiovascular responses mediated by the stimulation of alpha-2 adrenoceptors in the rat. | 1982 Nov |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Central muscarinic receptors signal pilocarpine-induced salivation. | 2003 Dec |
|
| Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. | 2003 Dec |
|
| Cardiac effects of hypocretin-1 in nucleus ambiguus. | 2003 Jun |
|
| 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 |
|
| Pharmacologic evidence for a parasympathetic role in seizure-induced neurocardiac regulatory abnormalities. | 2004 Feb |
|
| Evaluation of pseudo-affective responses to noxious colorectal distension in rats by manometric recordings. | 2005 Aug |
|
| The bradycardic and hypotensive responses to serotonin are reduced by activation of GABAA receptors in the nucleus tractus solitarius of awake rats. | 2005 Jul |
|
| Effects of angiotensin II on autonomic components of nasopharyngeal stimulation in male conscious rabbits. | 2005 May |
|
| Effects of AV3V lesion on pilocarpine-induced pressor response and salivary gland vasodilation. | 2005 Sep 7 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Final answer: ghrelin can suppress insulin secretion in humans, but is it clinically relevant? | 2010 Nov |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:51:55 UTC 2023
by
admin
on
Sat Dec 16 01:51:55 UTC 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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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
