Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:52 UTC |
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HMDB ID | HMDB0000473 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6-Dimethylaminopurine |
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Description | 6-Dimethylaminopurine, also known as 6,6-dimethyladenine or 6-DMAP, belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 6-Dimethylaminopurine is a puromycin analog that was first identified in the spores of Streptomyces alboniger (PMID: 5019066 ). It has subsequently been identified in several algae species (PMID: 4206669 ). 6-DMAP is widely used in the lab as a cell cycle inhibitor and a cyclin dependent kinase inhibitor. It also induces cell apoptosis. 6-DMAP is widely used for oocyte activation in eukaryotic cloning experiments (PMID: 29467049 ). |
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Structure | InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11) |
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Synonyms | Value | Source |
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6-(Dimethylamino)purine | ChEBI | 6-Dimethyladenine | ChEBI | N,N-Dimethyl-1H-purin-6-amine | ChEBI | N,N-Dimethyl-6-aminopurine | ChEBI | N,N-Dimethyladenine | ChEBI | N(6)-Dimethyladenine | ChEBI | 6,6-Dimethyladenine | HMDB | 6-(Dimethylamino)-purine | HMDB | 6-Dimethylamine purine | HMDB | Dimethyladenine | HMDB | DMAP | HMDB | N,N-Dimethyl-adenine | HMDB | N6,N6-Dimethyl-adenine | HMDB | N6,N6-Dimethyladenine | HMDB | 6-DMAP | HMDB | Dimethylaminopurine | HMDB | N(6),N(6)-Dimethyladenine | HMDB | 6-Dimethylaminopurine | ChEBI |
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Chemical Formula | C7H9N5 |
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Average Molecular Weight | 163.1799 |
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Monoisotopic Molecular Weight | 163.085795313 |
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IUPAC Name | N,N-dimethyl-7H-purin-6-amine |
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Traditional Name | 6-(dimethylamino)-purine |
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CAS Registry Number | 938-55-6 |
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SMILES | CN(C)C1=NC=NC2=C1NC=N2 |
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InChI Identifier | InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11) |
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InChI Key | BVIAOQMSVZHOJM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | 6-alkylaminopurines |
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Alternative Parents | |
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Substituents | - 6-alkylaminopurine
- Dialkylarylamine
- Aminopyrimidine
- Imidolactam
- Pyrimidine
- Heteroaromatic compound
- Imidazole
- Azole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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6-Dimethylaminopurine,1TMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N2 | 1813.1 | Semi standard non polar | 33892256 | 6-Dimethylaminopurine,1TMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N2 | 1735.4 | Standard non polar | 33892256 | 6-Dimethylaminopurine,1TMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C)C=N2 | 2588.0 | Standard polar | 33892256 | 6-Dimethylaminopurine,1TBDMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2 | 2018.3 | Semi standard non polar | 33892256 | 6-Dimethylaminopurine,1TBDMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2 | 1914.0 | Standard non polar | 33892256 | 6-Dimethylaminopurine,1TBDMS,isomer #1 | CN(C)C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2 | 2657.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 6-Dimethylaminopurine GC-MS (Non-derivatized) - 70eV, Positive | splash10-01pc-3900000000-b36f8c9c927f8edaa026 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Dimethylaminopurine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-Dimethylaminopurine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Dimethylaminopurine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0300-2900000000-3190d18e3cc2e66cc97d | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Dimethylaminopurine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-03di-0900000000-aab2d716306424dc0765 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 6-Dimethylaminopurine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-014l-9500000000-91620b9504a7308b12e6 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Positive-QTOF | splash10-03di-0900000000-93fb9b2f222378a415d7 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Positive-QTOF | splash10-03di-0900000000-c6797046cc77d63cba06 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Positive-QTOF | splash10-014i-0900000000-55b592d8f334e4afae80 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Negative-QTOF | splash10-03di-0900000000-266255a5066deb62d134 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Negative-QTOF | splash10-03di-0900000000-716bd3f65c301c7559b1 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Negative-QTOF | splash10-014i-1900000000-e5e0a5fa678fabe408c6 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Negative-QTOF | splash10-03di-0900000000-b97707ac300bd819a7b9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Negative-QTOF | splash10-03di-0900000000-6839a2c33d8f3a09762d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Negative-QTOF | splash10-014j-2900000000-9a0db3b19e645c745622 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 10V, Positive-QTOF | splash10-03di-0900000000-9cc41a9352cce06edd8d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 20V, Positive-QTOF | splash10-03di-0900000000-9cc41a9352cce06edd8d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-Dimethylaminopurine 40V, Positive-QTOF | splash10-0gbc-9100000000-958df0634af1082fff3f | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - Rime H, Neant I, Guerrier P, Ozon R: 6-Dimethylaminopurine (6-DMAP), a reversible inhibitor of the transition to metaphase during the first meiotic cell division of the mouse oocyte. Dev Biol. 1989 May;133(1):169-79. [PubMed:2540051 ]
- Anderiesz C, Fong CY, Bongso A, Trounson AO: Regulation of human and mouse oocyte maturation in vitro with 6-dimethylaminopurine. Hum Reprod. 2000 Feb;15(2):379-88. [PubMed:10655310 ]
- Sarngadharan MG, Pogell BM, Kariya M: Occurrence of new metabolites containing N 6 ,N 6 -dimethyladenine in spores of Streptomyces alboniger. Biochim Biophys Acta. 1972 Apr 12;262(4):405-9. doi: 10.1016/0005-2787(72)90483-2. [PubMed:5019066 ]
- Pakhomova MV: [N6-dimethylaminopurine in DNA of algae species]. Dokl Akad Nauk SSSR. 1974 Feb 11;214(5):1202-5. [PubMed:4206669 ]
- Kochan J, Nowak A, Nizanski W, Prochowska S, Migdal A, Mlodawska W, Partyka A, Witkowski M: Developmental competence of cat (Felis domesticus) oocytes and embryos after parthenogenetic stimulation using different methods. Zygote. 2018 Feb 22:1-8. doi: 10.1017/S0967199418000011. [PubMed:29467049 ]
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