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We show that reductive amination, forming secondary amines from aldehydes or ketones and amines, generates a previously hidden class of metabolites we term alkamines. Multiplexed synthesis of 8,475 alkamines combined with MS\/MS searches across 1.7 billion spectra identified 1,626 candidates across multiple species and organs. Of these, 56 were confirmed in biological samples, including 27 steroid- and 12 drug-derived alkamines matching prescription patterns. Notably, 77% of synthesized alkamines are absent from PubChem. This combinatorial logic likely explains why alkamines have evaded detection and suggests drug metabolism frameworks substantially underestimate drug-derived metabolite diversity. Reductive amination is an overlooked route modifying steroids, bile acids, and xenobiotics.<\/jats:p>","DOI":"10.64898\/2026.05.13.724743","type":"posted-content","created":{"date-parts":[[2026,5,16]],"date-time":"2026-05-16T01:30:14Z","timestamp":1778895014000},"source":"Crossref","is-referenced-by-count":1,"title":["Alkamines reveal a hidden layer of steroid and drug metabolism"],"prefix":"10.64898","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-0115-1997","authenticated-orcid":false,"given":"Julius","family":"Agongo","sequence":"first","affiliation":[{"name":"Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California; San Diego, La Jolla, CA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7422-4782","authenticated-orcid":false,"given":"Subhaskar R","family":"Panga","sequence":"additional","affiliation":[{"name":"Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California; San Diego, La Jolla, CA, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shipei","family":"Xing","sequence":"additional","affiliation":[{"name":"Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California; 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