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 |
In 1902, the Bayer company introduced first quaternary salt of atropine, methylatropine (nitrate salt), under the name of Eumydrin, as a mydriatic. Because of its highly polar nature it penetrated less readily into the central nervous system than did atropine; hence it was introduced for relieving pyloric spasm in infants. The drug has the same action as atropine and antagonizes muscarinic acetylcholine receptors.
CNS Activity
Sources: http://www.sigmaaldrich.com/catalog/product/sigma/sml0732?lang=es®ion=EShttps://www.ncbi.nlm.nih.gov/pubmed/19523969
Curator's Comment: Atropine methyl nitrate is a muscarinic acetylcholine receptor antagonist that does not cross the blood brain barrier.
Originator
Sources: Helgolaender Wissenschaftliche Meeresuntersuchungen (1966), 14, (1-2), 583-90.https://www.ncbi.nlm.nih.gov/pubmed/18799813
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Apparent reduction in baroreflex sensitivity to adenosine in conscious dogs. | 1985 Sep |
|
| 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 |
|
| Central muscarinic receptors signal pilocarpine-induced salivation. | 2003 Dec |
|
| Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. | 2003 Dec |
|
| 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 |
|
| 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 |
|
| 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 |
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.
for children: to begin with 1 to 2 drops daily and gradually increase the dose if necessary until the vomiting becomes less severe.
Route of Administration:
Topical
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 08:08:19 UTC 2023
by
admin
on
Thu Jul 06 08:08:19 UTC 2023
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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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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
