chemistry

Lysergic acid

Lysergic acid is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Lysergic acid rather than just read about it. In short: Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea species (morning glories, ololiuhqui, tlitliltzin). Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs, e.g. lysergic acid diethyl…

Key takeaways

Lysergic acid belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Lysergic acid to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Lysergic acid from memory before moving on to harder problems.

Reference excerpt

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea species (morning glories, ololiuhqui, tlitliltzin). Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs, e.g. lysergic acid diethylamide (LSD). Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. The name "lysergic acid" comes from the fact that it is a carboxylic acid, and it was first made by hydrolysis of various ergot alkaloids.

Pharmacology Lysergic acid failed to produce LSD-like electroencephalogram (EEG) changes in rabbits.

Chemistry

Synthesis

Laboratory Lysergic acid is generally produced by hydrolysis of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis, for example by Robert Burns Woodward's team in 1956. An enantioselective total synthesis based on a palladium-catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno. Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at 2 mmHg or 270 Pa) forms anhydrous lysergic acid.

Biosynthesis The biosynthetic route is based on the alkylation of the amino acid tryptophan with dimethylallyl diphosphate (isoprene derived from 3R-mevalonic acid) giving 4-dimethylallyl-L-tryptophan which is N-methylated with S-adenosyl-L-methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic isomerization yields D-(+)-lysergic acid. The biosynthetic pathway has been reconsituted in transgenic baker's yeast.

Illicit production Lysergic acid manufactured by clandestine chemists (also known as cooks) to use in the illictic synthesis of LSD is produced using Ergotamine tartrate or Ergometrinine.

Isomers Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at carbon atom 8 close to the carboxyl group is called isolysergic acid. Inversion at carbon 5 close to the nitrogen atom leads to L-lysergic acid and L-isolysergic acid, respectively.

Society and culture

Legal status

Canada Lysergic acid is a controlled substance in Canada.

United States In the United States, lysergic acid and lysergic acid amide (LSA; ergine) are Schedule III substances.

See also Ergine Lysergamides Paspalic acid

References

Illustrations

Worked examples

Example 1 — a first encounter with Lysergic acid

Start with the simplest possible case. Write down what Lysergic acid claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Lysergic acid before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Lysergic acid ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Lysergic acid

In research: Lysergic acid appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Lysergic acid in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Lysergic acid is common in secondary-school and first-year university syllabi. It links to neighbouring topics Beta-Amino acids, Ergolines, Total synthesis, so understanding it makes those chapters shorter.
In everyday life: Look for Lysergic acid outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Lysergic acid in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Lysergic acid means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Lysergic acid out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Lysergic acid in simple terms?

Why does Lysergic acid matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Lysergic acid?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Lysergic acid.