| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 05:51:45 UTC |
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| Updated at | 2022-09-02 05:51:45 UTC |
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| NP-MRD ID | NP0149900 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | n-{[3-(aminomethyl)phenyl]methyl}ethanimidamide |
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| Description | N-[3-(aminomethyl)benzyl]acetamidine, also known as 1400 W or W1400, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. N-[3-(aminomethyl)benzyl]acetamidine is a very strong basic compound (based on its pKa). n-{[3-(aminomethyl)phenyl]methyl}ethanimidamide is found in Crotalaria pallida. n-{[3-(aminomethyl)phenyl]methyl}ethanimidamide was first documented in 2001 (PMID: 11459438). An aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group (PMID: 25619924) (PMID: 26362773) (PMID: 26526764). |
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| Structure | InChI=1S/C10H15N3/c1-8(12)13-7-10-4-2-3-9(5-10)6-11/h2-5H,6-7,11H2,1H3,(H2,12,13) |
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| Synonyms | | Value | Source |
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| 1400 W | ChEBI | | 1400W | ChEBI | | W1400 | ChEBI | | 1400W CPD | MeSH |
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| Chemical Formula | C10H15N3 |
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| Average Mass | 177.2462 Da |
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| Monoisotopic Mass | 177.12660 Da |
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| IUPAC Name | N-{[3-(aminomethyl)phenyl]methyl}ethanimidamide |
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| Traditional Name | N-{[3-(aminomethyl)phenyl]methyl}ethanimidamide |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=N)NCC1=CC=CC(CN)=C1 |
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| InChI Identifier | InChI=1S/C10H15N3/c1-8(12)13-7-10-4-2-3-9(5-10)6-11/h2-5H,6-7,11H2,1H3,(H2,12,13) |
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| InChI Key | RODUKNYOEVZQPR-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. |
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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 | Phenylmethylamines |
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| Direct Parent | Phenylmethylamines |
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| Alternative Parents | |
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| Substituents | - Benzylamine
- Phenylmethylamine
- Aralkylamine
- Amidine
- Carboxylic acid amidine
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organopnictogen compound
- Organonitrogen compound
- Primary aliphatic amine
- Primary amine
- Organic nitrogen compound
- Amine
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Menchen LA, Colon AL, Moro MA, Leza JC, Lizasoain I, Menchen P, Alvarez E, Lorenzo P: N-(3-(aminomethyl)benzyl)acetamidine, an inducible nitric oxide synthase inhibitor, decreases colonic inflammation induced by trinitrobenzene sulphonic acid in rats. Life Sci. 2001 Jun 15;69(4):479-91. doi: 10.1016/s0024-3205(01)01139-0. [PubMed:11459438 ]
- Overso Hansen P, Kringelholt S, Simonsen U, Bek T: Hypoxia-induced relaxation of porcine retinal arterioles in vitro depends on inducible NO synthase and EP4 receptor stimulation in the perivascular retina. Acta Ophthalmol. 2015 Aug;93(5):457-63. doi: 10.1111/aos.12669. Epub 2015 Jan 25. [PubMed:25619924 ]
- Gautam M, Kumar R, Prasoon P, Ray SB: Antinociceptive effect of 1400 W, an inhibitor of inducible nitric oxide synthase, following hind paw incision in rats. Nitric Oxide. 2015 Nov 15;50:98-104. doi: 10.1016/j.niox.2015.09.003. Epub 2015 Sep 8. [PubMed:26362773 ]
- Guo C, Atochina-Vasserman E, Abramova H, George B, Manoj V, Scott P, Gow A: Role of NOS2 in pulmonary injury and repair in response to bleomycin. Free Radic Biol Med. 2016 Feb;91:293-301. doi: 10.1016/j.freeradbiomed.2015.10.417. Epub 2015 Oct 23. [PubMed:26526764 ]
- LOTUS database [Link]
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