Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:43:11 UTC |
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Updated at | 2021-08-19 23:59:31 UTC |
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NP-MRD ID | NP0002901 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Neostigmine |
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Provided By | BMRB |
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Description | Neostigmine, also known as proserine or synstigmin, belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. It was first documented in 1982 (PMID: 7200780). Based on a literature review a significant number of articles have been published on Neostigmine (PMID: 17984079) (PMID: 8584207) (PMID: 34601981) (PMID: 34599343). |
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Structure | CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1 |
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Synonyms | Value | Source |
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(m-Hydroxyphenyl)trimethylammonium dimethylcarbamate | ChEBI | 3-Trimethylammoniumphenyl N,N-dimethylcarbamate | ChEBI | Eustigmin | ChEBI | Eustigmine | ChEBI | m-Trimethylammoniumphenyldimethylcarbamate | ChEBI | Prostigmine | ChEBI | Vagostigmine | ChEBI | Prostigmin | Kegg | (m-Hydroxyphenyl)trimethylammonium dimethylcarbamic acid | Generator | 3-Trimethylammoniumphenyl N,N-dimethylcarbamic acid | Generator | m-Trimethylammoniumphenyldimethylcarbamic acid | Generator | Proserine | HMDB | Neostigmine bromide | HMDB | Methylsulfate, neostigmine | HMDB | Polstigmine | HMDB | Syntostigmine | HMDB | Bromide, neostigmine | HMDB | Neostigmine methylsulfate | HMDB | Prozerin | HMDB | Synstigmin | HMDB |
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Chemical Formula | C12H19N2O2 |
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Average Mass | 223.2915 Da |
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Monoisotopic Mass | 223.14465 Da |
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IUPAC Name | 3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium |
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Traditional Name | neostigmine |
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CAS Registry Number | Not Available |
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SMILES | CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C |
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InChI Identifier | InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1 |
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InChI Key | ALWKGYPQUAPLQC-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenoxy compounds |
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Direct Parent | Phenoxy compounds |
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Alternative Parents | |
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Substituents | - Phenoxy compound
- Aniline or substituted anilines
- Quaternary ammonium salt
- Carbamic acid ester
- Carbonic acid derivative
- Amine
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic salt
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic cation
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Sobek V: The effect of calcium, neostigmine and 4-aminopyridine upon respiratory arrest and depression of cardiovascular functions after aminoglycosidic antibiotics. Arzneimittelforschung. 1982;32(3):222-4. [PubMed:7200780 ]
- Shen E, Sun X: Endogenous acetylcholine-induced Fos expression in magnocellular neurosecretory neurons in the supraoptic nucleus of the rat hypothalamus. Neurosci Lett. 1995 Aug 11;195(3):191-4. doi: 10.1016/0304-3940(95)11816-f. [PubMed:8584207 ]
- Hile GB, Healy KJ, Almassalkhi LR: Rocuronium Reversal in the Emergency Department: Retrospective Evaluation of Hemodynamic Instability Following Administration of Sugammadex Versus Neostigmine With Glycopyrrolate. J Pharm Pract. 2021 Oct 2:8971900211048747. doi: 10.1177/08971900211048747. [PubMed:34601981 ]
- Deng J, Balouch M, Albrink M, Camporesi EM: Sugammadex Reduces PACU Recovery Time after Abdominal Surgery Compared with Neostigmine. South Med J. 2021 Oct;114(10):644-648. doi: 10.14423/SMJ.0000000000001304. [PubMed:34599343 ]
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