Thiamine monophosphate
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| verifiedrevid = 470606219
| ImageFile=Thiamine monophosphate.svg
| ImageSize=250px
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|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10307
| InChI = 1/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H
| InChIKey = GUGWNSHJDUEHNJ-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GUGWNSHJDUEHNJ-UHFFFAOYSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 71F2V60NN0
| CASNo= 10023-48-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 10761
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9533
| SMILES = Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)O.[Cl-]
| MeSHName=Thiamine+Monophosphate
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|Section2={{Chembox Properties
| Formula=C12H18N4O4PS+
| MolarMass=345.336 g/mol
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Thiamine monophosphate, also known as ThMP and TMP, is a phosphate ester of thiamine.{{cite journal | vauthors = Mancinelli R, Ceccanti M, Guiducci MS, Sasso GF, Sebastiani G, Attilia ML, Allen JP | title = Simultaneous liquid chromatographic assessment of thiamine, thiamine monophosphate and thiamine diphosphate in human erythrocytes: a study on alcoholics | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 789 | issue = 2 | pages = 355–363 | date = June 2003 | pmid = 12742126 | doi = 10.1016/S1570-0232(03)00139-9 }}
It is an intermediate from the hydrolysis of thiamine diphosphate to free thiamine by alkaline phosphatase.{{cite journal | vauthors = Lonsdale D | title = Thiamin | journal = Advances in Food and Nutrition Research | volume = 83 | pages = 1–56 | date = 2018 | pmid = 29477220 | doi = 10.1016/bs.afnr.2017.11.001 | publisher = Elsevier | isbn = 978-0-12-811803-0 }}{{cite book | vauthors = Lonsdale D, Marrs C | chapter = Chapter 3 - Mitochondria, Thiamine, and Autonomic Dysfunction |date= January 2017 | veditors = Lonsdale D, Marrs C | title = Thiamine Deficiency Disease, Dysautonomia, and High Calorie Malnutrition |pages=59–103 |publisher=Academic Press |doi=10.1016/b978-0-12-810387-6.00003-4 |isbn=978-0-12-810387-6 }}{{cite journal | vauthors = Gangolf M, Czerniecki J, Radermecker M, Detry O, Nisolle M, Jouan C, Martin D, Chantraine F, Lakaye B, Wins P, Grisar T, Bettendorff L | title = Thiamine status in humans and content of phosphorylated thiamine derivatives in biopsies and cultured cells | journal = PLOS ONE | volume = 5 | issue = 10 | pages = e13616 | date = October 2010 | pmid = 21049048 | pmc = 2963613 | doi = 10.1371/journal.pone.0013616 | doi-access = free | bibcode = 2010PLoSO...513616G | veditors = German M }} The conversion of ThMP to thiamine cannot be facilitated by acid hydrolysis.{{cite journal | vauthors = Burch HB, Bessey OA, Love RH, Lowry OH | title = The determination of thiamine and thiamine phosphates in small quantities of blood and blood cells | journal = The Journal of Biological Chemistry | volume = 198 | issue = 1 | pages = 477–490 | date = September 1952 | pmid = 12999762 | doi = 10.1016/s0021-9258(18)55601-5 | doi-access = free }} ThMP is also enzymatically synthesized by thiamine-phosphate pyrophosphorylase, which combines thiazole in its monophosphate form and pyrimidine as a pyrophosphate.{{cite journal | vauthors = Leder IG | title = The enzymatic synthesis of thiamine monophosphate | journal = The Journal of Biological Chemistry | volume = 236 | issue = 11 | pages = 3066–3071 | date = November 1961 | pmid = 14463407 | doi = 10.1016/s0021-9258(19)76430-8 | doi-access = free }}
Physiological presence
In whole human blood, both ThMP and free thiamine are present in lower concentrations as compared to TPP, but they are found in low amounts in plasma. ThMP is the only phosphorylated thiamine derivative found in human cerebral spinal fluid.{{cite journal | vauthors = Rindi G, Patrini C, Poloni M | title = Monophosphate, the only phosphoric ester of thiamin in the cerebro-spinal fluid | journal = Experientia | volume = 37 | issue = 9 | pages = 975–976 | date = September 1981 | pmid = 7297660 | doi = 10.1007/BF01971788 }}
In rats, approximately 64% of the total thiamine in plasma exists in its the monophosphate form.{{cite journal | vauthors = Rindi G, De Giuseppe L, Sciorelli G | title = Thiamine monophosphate, a normal constituent of rat plasma | journal = The Journal of Nutrition | volume = 94 | issue = 4 | pages = 447–454 | date = April 1968 | pmid = 4297480 | doi = 10.1093/jn/94.4.447 }} After injection of ThMP into the femoral vein of rats, it was quickly transported to the cerebral tissue without chemical modification, but the average transport rate was 5-10 times slower than that of thiamine.{{cite journal | vauthors = Reggiani C, Patrini C, Rindi G | title = Nervous tissue thiamine metabolism in vivo. I. Transport of thiamine and thiamine monophosphate from plasma to different brain regions of the rat | journal = Brain Research | volume = 293 | issue = 2 | pages = 319–327 | date = February 1984 | pmid = 6697223 | doi = 10.1016/0006-8993(84)91239-3 }}