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As distinct acute pain, neuropathic pain is chronic, and it severely influences quality of life. <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010Dimethyl\u2010<jats:sc>d<\/jats:sc>\u2010<jats:italic>erythro<\/jats:italic>\u2010sphingosine (DMS), a neuropathic pain inducer, is metabolited de novo from sphingosine. In a recent study, metabolomics showed an increased concentration level of DMS in the spinal cord in mice with neuropathic pain. Nerve growth factor (NGF) is one of the peripheral nervous system targeted pain factors that interact with tropomyosin receptor kinase A (trkA). On the basis of this information, we were interested in the possibility that DMS may induce neuropathic pain\u2010like behavior through an increase of NGF activity. In this study, we showed that DMS can enhance the binding of NGF to trkA, followed by neurite outgrowth of epidermal nerve fibers and phosphorylation of trkA. In addition, a stereoisomer, <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethyl\u2010<jats:sc>l<\/jats:sc>\u2010<jats:italic>erythro<\/jats:italic>\u2010sphingosine, did not any show such biological activities. The results suggest that DMS can enhance the binding of NGF to trkA and that its stereochemistry is an essential factor for exhibiting its activity.<\/jats:p>","DOI":"10.1002\/chir.23433","type":"journal-article","created":{"date-parts":[[2022,3,17]],"date-time":"2022-03-17T06:06:36Z","timestamp":1647497196000},"page":"807-812","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Evaluation of chiral <i>N<\/i>,<i>N<\/i>\u2010dimethyl\u2010sphingosine for the interaction between nerve growth factor and tropomyosin receptor kinase A"],"prefix":"10.1002","volume":"34","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9115-6478","authenticated-orcid":false,"given":"Yuta","family":"Murai","sequence":"first","affiliation":[{"name":"Graduate School of Life Science Hokkaido University  Sapporo Japan"},{"name":"Faculty of Advanced Life Science Hokkaido University  Sapporo 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