Chemistry and Structure
LSD is an ergoline derivative. It is commonly synthesised by reacting diethylamine with an activated form of lysergic acid. Activating reagents include phosphoryl chloride and peptide coupling reagents. Lysergic acid is made by alkaline hydrolysis of lysergamides like ergotamine, a substance derived from the ergot fungus on rye, or from ergine (lysergic acid amide, LSA), a compound that is found in morning glory (Ipomoea tricolor) and Hawaiian baby woodrose (Argyreia nervosa) seeds.
LSD is a chiral compound with two stereocenters at the carbon atoms C-5 and C-8, so that theoretically four different optical isomers of LSD could exist. LSD, also called (+)--LSD, has the absolute configuration (5R,8R). The C-5 isomers of lysergamides do not exist in nature and are not formed during the synthesis from -lysergic acid. Retrosynthetically, the C-5 stereocenter could be analysed as having the same configuration of the alpha carbon of the naturally occurring amino acid L-tryptophan, the precursor to all biosynthetic ergoline compounds.
However, LSD and iso-LSD, the two C-8 isomers, rapidly interconvert in the presence of bases, as the alpha proton is acidic and can be deprotonated and reprotonated. Non-psychoactive iso-LSD which has formed during the synthesis can be separated by chromatography and can be isomerized to LSD.
A totally pure salt of LSD will emit small flashes of white light when shaken in the dark. LSD is strongly fluorescent and will glow bluish-white under UV light.
Read more about this topic: Lysergic Acid Diethylamide
Famous quotes containing the words chemistry and/or structure:
“...some sort of false logic has crept into our schools, for the people whom I have seen doing housework or cooking know nothing of botany or chemistry, and the people who know botany and chemistry do not cook or sweep. The conclusion seems to be, if one knows chemistry she must not cook or do housework.”
—Ellen Henrietta Swallow Richards (1842–1911)
“There is no such thing as a language, not if a language is anything like what many philosophers and linguists have supposed. There is therefore no such thing to be learned, mastered, or born with. We must give up the idea of a clearly defined shared structure which language-users acquire and then apply to cases.”
—Donald Davidson (b. 1917)