Editing Alkaloid (section)

== Properties ==
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as [[nicotine]]<ref>{{GSEn|081823|Никотин}}</ref> or [[coniine]],<ref name="BSE: koniin"/> are typically volatile, colorless, oily liquids.<ref name="ref222">[[#Grinkevich|Grinkevich]], p. 131</ref> Some alkaloids are colored, like [[berberine]] (yellow) and [[sanguinarine]] (orange).<ref name="ref222" />

Most alkaloids are weak bases, but some, such as [[theobromine]] and [[theophylline]], are [[amphoteric]].<ref name="ref225">{{Cite book |last=Spiller |first=Gene A. |url=https://books.google.com/books?id=Rgs_rVOceZwC&pg=PA140 |title=Caffeine |date=2019-04-23 |publisher=CRC Press |isbn=978-1-4200-5013-4 |pages=140 |language=en}}</ref> Many alkaloids dissolve poorly in water but readily dissolve in [[organic solvent]]s, such as [[diethyl ether]], [[chloroform]] or [[1,2-dichloroethane]]. [[Caffeine]],<ref>{{cite web|title=Caffeine|url=http://www.drugbank.ca/drugs/DB00201|work=DrugBank|access-date=12 February 2013}}</ref> [[cocaine]],<ref>{{cite web|title=Cocaine|url=http://www.drugbank.ca/drugs/DB00907|work=DrugBank|access-date=12 February 2013}}</ref> [[codeine]]<ref>{{cite web|title=Codeine|url=http://www.drugbank.ca/drugs/DB00318|work=DrugBank|access-date=12 February 2013}}</ref> and [[nicotine]]<ref>{{cite web|title=Nicotine|url=http://www.drugbank.ca/drugs/DB00184|work=DrugBank|access-date=12 February 2013}}</ref> are slightly soluble in water (with a solubility of ≥1g/L), whereas others, including [[morphine]]<ref>{{cite web|title=Morphine|url=http://www.drugbank.ca/drugs/DB00295|work=DrugBank|access-date=12 February 2013}}</ref> and [[yohimbine]]<ref>{{cite web|title=Yohimbine |url=http://www.drugbank.ca/drugs/DB01392 |work=DrugBank |access-date=12 February 2013 |url-status=dead |archive-url=https://web.archive.org/web/20130130101146/http://www.drugbank.ca/drugs/DB01392 |archive-date=30 January 2013 }}</ref> are very slightly water-soluble (0.1–1 g/L). Alkaloids and acids form salts of various strengths. These salts are usually freely soluble in water and [[ethanol]] and poorly soluble in most organic solvents. Exceptions include [[Hyoscine hydrobromide|scopolamine]] hydrobromide, which is soluble in organic solvents, and the water-soluble quinine sulfate.<ref name="ref222" />

Most alkaloids have a bitter taste or are poisonous when ingested. Alkaloid production in plants appeared to have evolved in response to feeding by herbivorous animals; however, some animals have evolved the ability to detoxify alkaloids.<ref>[[#Fattorusso|Fattorusso]], p. 53</ref> Some alkaloids can produce developmental defects in the offspring of animals that consume but cannot detoxify the alkaloids. One example is the alkaloid [[cyclopamine]], produced in the leaves of [[Veratrum californicum|corn lily]]. During the 1950s, up to 25% of lambs born by sheep that had grazed on corn lily had serious facial deformations. These ranged from deformed jaws to [[cyclopia]]. After decades of research, in the 1980s, the compound responsible for these deformities was identified as the alkaloid 11-deoxyjervine, later renamed to cyclopamine.<ref>{{cite book|page=362|url=https://books.google.com/books?id=nixyqfGIGHcC&pg=PA362|title=Poisonous plants and related toxins, Volume 2001|author1=Thomas Acamovic |author2=Colin S. Stewart |author3=T. W. Pennycott |publisher=CABI|year= 2004|isbn=978-0-85199-614-1}}</ref>