Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C18H26NO3 |
| Molecular Weight | 304.4039 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 5 |
| 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 / 5 |
| 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 |
unhealthy, 1 week |
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 |
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 |
Other AEs: Paralytic ileus... |
16 mg multiple, oral Highest studied dose |
unhealthy, 7 weeks |
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 Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
unhealthy, babies |
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 |
unhealthy, 1 week |
| Paralytic ileus | 1 patient | 0.8 mg multiple, oral |
unhealthy, 1 week |
| 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 |
|
| 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 |
|
| 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 |
| Dilated pupils | 1 patient | 16 mg multiple, oral Highest studied dose |
unhealthy, 7 weeks |
| Hypertonia | 1 patient | 16 mg multiple, oral Highest studied dose |
unhealthy, 7 weeks |
| Irritable | 1 patient | 16 mg multiple, oral Highest studied dose |
unhealthy, 7 weeks |
| Abdominal distension | Disc. AE | 0.1 mg 1 times / day multiple, oral Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
unhealthy, babies |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Final answer: ghrelin can suppress insulin secretion in humans, but is it clinically relevant? | 2010-11 |
|
| Xenin-25 potentiates glucose-dependent insulinotropic polypeptide action via a novel cholinergic relay mechanism. | 2010-06-25 |
|
| Effect of ghrelin on glucose-insulin homeostasis: therapeutic implications. | 2010 |
|
| Modulation of heart rate variability during severe hemorrhage at different rates in conscious rats. | 2009-10-05 |
|
| Post-exposure treatment with nasal atropine methyl bromide protects against microinstillation inhalation exposure to sarin in guinea pigs. | 2009-09-15 |
|
| The analgesic effect of crotoxin on neuropathic pain is mediated by central muscarinic receptors and 5-lipoxygenase-derived mediators. | 2008-12 |
|
| Ghrelin infused into the portal vein inhibits glucose-stimulated insulin secretion in Wistar rats. | 2008-07 |
|
| Medullary pathways mediating the parasubthalamic nucleus depressor response. | 2008-04 |
|
| Acute induction of epileptiform discharges by pilocarpine in the in vitro isolated guinea-pig brain requires enhancement of blood-brain barrier permeability. | 2008-01-02 |
|
| Medical countermeasure against respiratory toxicity and acute lung injury following inhalation exposure to chemical warfare nerve agent VX. | 2007-03 |
|
| Cardiovascular responses produced by central injection of hydrogen peroxide in conscious rats. | 2006-12-11 |
|
| Facilitation of cardiac vagal activity by CRF-R1 antagonists during swim stress in rats. | 2006-12 |
|
| Sympathetic and parasympathetic component of bradycardia triggered by stimulation of NTS P2X receptors. | 2006-02 |
|
| Effects of AV3V lesion on pilocarpine-induced pressor response and salivary gland vasodilation. | 2005-09-07 |
|
| Evaluation of pseudo-affective responses to noxious colorectal distension in rats by manometric recordings. | 2005-08 |
|
| The bradycardic and hypotensive responses to serotonin are reduced by activation of GABAA receptors in the nucleus tractus solitarius of awake rats. | 2005-07 |
|
| Effects of angiotensin II on autonomic components of nasopharyngeal stimulation in male conscious rabbits. | 2005-05 |
|
| Pharmacologic evidence for a parasympathetic role in seizure-induced neurocardiac regulatory abnormalities. | 2004-02 |
|
| Central muscarinic receptors signal pilocarpine-induced salivation. | 2003-12 |
|
| Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. | 2003-12 |
|
| Cardioacceleratory responses to hypocretin-1 injections into rostral ventromedial medulla. | 2003-11-21 |
|
| 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. | 2003-11 |
|
| Dual effects of acupuncture on gastric motility in conscious rats. | 2003-10 |
|
| Cardiac effects of hypocretin-1 in nucleus ambiguus. | 2003-06 |
|
| Cardiovascular effects of hypocretin-1 in nucleus of the solitary tract. | 2003-04 |
|
| Bupivacaine inhibits baroreflex control of heart rate in conscious rats. | 2000-01 |
|
| The role of cholinergic systems in the expression of morphine withdrawal. | 1996-06 |
|
| Endogenous gamma-aminobutyric acid (GABA) mediates ethanol inhibition of vagally mediated reflex bradycardia elicited from aortic baroreceptors. | 1994-02 |
|
| L-glutamate stimulation of the zona incerta in the rat decreases heart rate and blood pressure. | 1988-08-16 |
|
| Central interactions between dihydropyridines and cholinergic systems in the control of blood pressure in rat. | 1987-12-01 |
|
| Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin. | 1986-02 |
|
| Apparent reduction in baroreflex sensitivity to adenosine in conscious dogs. | 1985-09 |
|
| Participation of cholinergic pathways in sinoaortic denervated rats. | 1985 |
|
| [Effects of oxybutynin on the cardiovascular system in dogs]. | 1984-10 |
|
| Pharmacological, hemodynamic and autonomic nervous system mechanisms responsible for the blood pressure and heart rate lowering effects of pergolide in rats. | 1984-03 |
|
| Excess tachycardia: heart rate after antimuscarinic agents in conscious dogs. | 1984-02 |
|
| Drugs for Parkinson's disease reduce tremor induced by physostigmine. | 1983-07 |
|
| Urethane inhibits cardiovascular responses mediated by the stimulation of alpha-2 adrenoceptors in the rat. | 1982-11 |
|
| Changes in blood-brain barrier permeability to drugs in decompressed rats. | 1982-09 |
|
| Cardiovascular responses to intracisternal administration of nicotine in rats. | 1981-06 |
|
| Quantification of tremor in rats induced by physostigmine. | 1981 |
|
| Effect of thyrotropin-releasing hormone (TRH) on local cerebral glucose utilization, by the autoradiographic 2-deoxy[14C]glucose method, in conscious and pentobarbitalized rats. | 1980-10 |
|
| Influence of several anesthetic agents on the effect of delta9-tetrahydrocannabinol on the heart rate and blood pressure of the mongrel dog. | 1977-07-01 |
|
| Analysis of cardiac chronotropic responses to diazepam and bromazepam in conscious trained dogs. | 1976-02 |
|
| The difference in the effects of tertiary and quaternary ammonium bases (proserine, serine, methylatropine and atropine) depending on the method of administration. | 1962-03 |
|
| Ganglionic blocking action of atropine and methylatropine. | 1953-12 |
|
| Clinical pertussis treated with methyl atropine nitrate (eumydrin). | 1950-10-07 |
|
| Effects of atropine sulfate, methylatropine nitrate (metropine) and homatropine hydrobromide on adult human eyes. | 1946-09 |
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
Mon Mar 31 21:01:56 GMT 2025
by
admin
on
Mon Mar 31 21:01:56 GMT 2025
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| Record UNII |
80719I460H
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| Record Status |
Validated (UNII)
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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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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
