Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-25 22:32:00 UTC |
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Update Date | 2016-11-09 01:18:08 UTC |
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Accession Number | CHEM025664 |
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Identification |
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Common Name | Acetylcholine |
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Class | Small Molecule |
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Description | Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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ACh | ChEBI | Azetylcholin | ChEBI | Choline acetate | ChEBI | O-Acetylcholine | ChEBI | Choline acetic acid | Generator | Acetylcholine iodide | HMDB | Acetylcholine perchlorate | HMDB | Acetylcholine sulfate (1:1) | HMDB | Bromoacetylcholine | HMDB | Cusi, acetilcolina | HMDB | Iodide, acetylcholine | HMDB | 2-(Acetyloxy)-N,N,N-trimethylethanaminium | HMDB | Acetilcolina cusi | HMDB | Acetylcholine fluoride | HMDB | Acetylcholine L tartrate | HMDB | Acetylcholine picrate | HMDB | Chloroacetylcholine | HMDB | Miochol | HMDB | Perchlorate, acetylcholine | HMDB | Acetylcholine L-tartrate | HMDB | Acetylcholine picrate (1:1) | HMDB | Hydroxide, acetylcholine | HMDB | Acetylcholine bromide | HMDB | Acetylcholine chloride | HMDB | Acetylcholine hydroxide | HMDB | Bromide, acetylcholine | HMDB | Fluoride, acetylcholine | HMDB | L-Tartrate, acetylcholine | HMDB | Acetyl choline ion | HMDB | Acetylcholine cation | HMDB | Acetylcholinium: acetyl-choline | HMDB | Choline acetate (ester) | HMDB | Bournonville brand OF acetylcholine chloride | HMDB | Iolab brand OF acetylcholine chloride | HMDB | Alcon brand OF acetylcholine chloride | HMDB | Ciba vision brand OF acetylcholine chloride | HMDB | Acetylcholine | MeSH, HMDB |
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Chemical Formula | C7H16NO2 |
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Average Molecular Mass | 146.207 g/mol |
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Monoisotopic Mass | 146.118 g/mol |
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CAS Registry Number | 51-84-3 |
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IUPAC Name | [2-(acetyloxy)ethyl]trimethylazanium |
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Traditional Name | acetylcholine |
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SMILES | CC(=O)OCC[N+](C)(C)C |
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InChI Identifier | InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1 |
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InChI Key | OIPILFWXSMYKGL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Quaternary ammonium salts |
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Direct Parent | Acyl cholines |
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Alternative Parents | |
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Substituents | - Acyl choline
- Tetraalkylammonium salt
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Carbonyl group
- Amine
- Organic cation
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4r-9100000000-bf8d3f373f038db1a310 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000j-9600000000-ec60451904fda7dde556 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000l-9000000000-2ea4c086c3ab458a1d7c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-98d5a70eed75a0945da4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0002-1900000000-2da10e016ac539b6e981 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-9000000000-7efaaa08a6c43d816358 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-000i-9000000000-eb7d66198d7674cbbd2a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-000l-9000000000-41b87d773c58129802e9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9000000000-9e8e66250f2cf34a2046 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0002-0900000000-f7fe18f2371596dc7333 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-000j-9800000000-b0f987ebcb0179a2c5ab | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-9000000000-1be58612df9c1eef1282 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0002-1900000000-2da10e016ac539b6e981 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-9000000000-7efaaa08a6c43d816358 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-9000000000-eb7d66198d7674cbbd2a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000l-9000000000-41b87d773c58129802e9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-9ac44e29bdfbddf1b90d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-f7fe18f2371596dc7333 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000j-9800000000-b0f987ebcb0179a2c5ab | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-000j-9400000000-8a3a0b77e93715b85ed4 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB03128 |
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HMDB ID | HMDB0000895 |
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FooDB ID | FDB012191 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00054040 |
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BiGG ID | 38868 |
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BioCyc ID | ACETYLCHOLINE |
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METLIN ID | 57 |
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PDB ID | Not Available |
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Wikipedia Link | Acetylcholine |
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Chemspider ID | 182 |
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ChEBI ID | 15355 |
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PubChem Compound ID | 187 |
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Kegg Compound ID | C01996 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14764638 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15014918 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15231705 | 4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15361288 | 5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18050502 | 6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18407448 | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19255787 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20963497 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21130809 | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21246223 | 11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21545631 | 12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21601579 | 13. Szutowicz, Andrzej. Acetylcholine synthesis in synaptosomes. Postepy Biochemii (1979), 25(1), 59-84. | 14. Nguyen VT, Ndoye A, Hall LL, Zia S, Arredondo J, Chernyavsky AI, Kist DA, Zelickson BD, Lawry MA, Grando SA: Programmed cell death of keratinocytes culminates in apoptotic secretion of a humectant upon secretagogue action of acetylcholine. J Cell Sci. 2001 Mar;114(Pt 6):1189-204. | 15. Chia S, Megson IL, Ludlam CA, Fox KA, Newby DE: Preserved endothelial vasomotion and fibrinolytic function in patients with acute stent thrombosis or in-stent restenosis. Thromb Res. 2003;111(6):343-9. | 16. Grando SA, Kist DA, Qi M, Dahl MV: Human keratinocytes synthesize, secrete, and degrade acetylcholine. J Invest Dermatol. 1993 Jul;101(1):32-6. | 17. Beilin B, Bessler H, Papismedov L, Weinstock M, Shavit Y: Continuous physostigmine combined with morphine-based patient-controlled analgesia in the postoperative period. Acta Anaesthesiol Scand. 2005 Jan;49(1):78-84. | 18. Tao J, Jin YF, Yang Z, Wang LC, Gao XR, Lui L, Ma H: Reduced arterial elasticity is associated with endothelial dysfunction in persons of advancing age: comparative study of noninvasive pulse wave analysis and laser Doppler blood flow measurement. Am J Hypertens. 2004 Aug;17(8):654-9. | 19. Jiang JL, Jiang DJ, Tang YH, Li NS, Deng HW, Li YJ: Effect of simvastatin on endothelium-dependent vaso-relaxation and endogenous nitric oxide synthase inhibitor. Acta Pharmacol Sin. 2004 Jul;25(7):893-901. | 20. Haug KH, Bogen IL, Osmundsen H, Walaas I, Fonnum F: Effects on cholinergic markers in rat brain and blood after short and prolonged administration of donepezil. Neurochem Res. 2005 Dec;30(12):1511-20. | 21. Katoh H, Shimada T, Inoue S, Takahashi N, Shimizu H, Ohta Y, Nakamura K, Murakami Y, Ishibashi Y, Matsumori A: Reduced high serum hepatocyte growth factor levels after successful cardioversion in patients with atrial fibrillation. Clin Exp Pharmacol Physiol. 2004 Mar;31(3):145-51. | 22. Main C, Blennerhassett P, Collins SM: Human recombinant interleukin 1 beta suppresses acetylcholine release from rat myenteric plexus. Gastroenterology. 1993 Jun;104(6):1648-54. | 23. Ikarashi Y, Harigaya Y, Tomidokoro Y, Kanai M, Ikeda M, Matsubara E, Kawarabayashi T, Kuribara H, Younkin SG, Maruyama Y, Shoji M: Decreased level of brain acetylcholine and memory disturbance in APPsw mice. Neurobiol Aging. 2004 Apr;25(4):483-90. | 24. Katz SD, Krum H: Acetylcholine-mediated vasodilation in the forearm circulation of patients with heart failure: indirect evidence for the role of endothelium-derived hyperpolarizing factor. Am J Cardiol. 2001 May 1;87(9):1089-92. | 25. Hanna ST, Cao K, Wang R: Interaction of acetylcholine with Kir6.1 channels heterologously expressed in human embryonic kidney cells. Eur J Pharmacol. 2005 May 16;515(1-3):34-42. | 26. Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK: Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. Epub 2005 Nov 7. | 27. Shirahata M, Balbir A, Otsubo T, Fitzgerald RS: Role of acetylcholine in neurotransmission of the carotid body. Respir Physiol Neurobiol. 2007 Jul 1;157(1):93-105. Epub 2007 Jan 11. | 28. Hasselmo ME: The role of acetylcholine in learning and memory. Curr Opin Neurobiol. 2006 Dec;16(6):710-5. Epub 2006 Sep 29. | 29. Beane M, Marrocco RT: Norepinephrine and acetylcholine mediation of the components of reflexive attention: implications for attention deficit disorders. Prog Neurobiol. 2004 Oct;74(3):167-81. | 30. Mezzelani A, Landini M, Facchiano F, Raggi ME, Villa L, Molteni M, De Santis B, Brera C, Caroli AM, Milanesi L, Marabotti A: Environment, dysbiosis, immunity and sex-specific susceptibility: a translational hypothesis for regressive autism pathogenesis. Nutr Neurosci. 2015 May;18(4):145-61. doi: 10.1179/1476830513Y.0000000108. Epub 2014 Jan 21. | 31. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. | 32. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. |
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