Lysergic Acid Diethylamide

For this month's post on  a chiral compound, I chose Lysergic Acid Diethylamide, or more as it is more commonly known, LSD. This chemical was specifically compelling because it's chirality is the source of its activity. To start, here is the chemical structure of LSD:

LSD is an ergot derivative. Ergot, a fungus that often grows on Rye, was thought to simply be a part of the Rye grain until the 1850s. Individuals that were infected after consuming Ergot poisoning experience a variety of symptoms. Interestingly enough, if one is infected multiple times, different symptoms are experienced each time. The most common symptom of Ergot consumption is called 'ergotism.' Victims claim to have immense bodily pain, confusions, muscle spasms, and hallucinations. An alternate form of ergotism, called gangrenous ergotism also exists. In this form, parts of the extremities are lost. This is the cause of gangrene, due to the restriction of blood to those parts of the body.

The real science behind how LSD a derivative of this fungus is extremely interesting. The chiral centers of LSD are responsible for it's reactivity. The two cyclic coordinated Nitrogens are the site of LSD's reactive centers. LSD's chiral centers exist as R-R. Without this stereo-chemistry, the hallucinogen qualities are almost completely gone. It is more than twenty times more psychologically active than its enatiomer. This is due to the binding affinity of R-R LSD to a receptor.

http://www.maps.org/research/lsd/swisslsd/IB_LSD.pdf
http://www.botany.hawaii.edu/faculty/wong/BOT135/LECT12.HTM

Pfaff, R. C.; Huang, X.; Marona-Lewicka, D.; Oberlender, R.; and Nichols, D. E.; Lysergamides Revisited, in Hallucinogens: An Update, 1994 , Editors: Geraline C. Lin & Richard A. Glennon, NIDA Research Monograph No. 146, National Institute on Drug Abuse, pp 52-73; Brimblecombe, R.W.; Pinder, R.M.; Hallucinogenic Agents , 1975 , Wright-Scientechnica, Bristol, UK