Lysergic Acid Hydroxyethylamide

Lysergic acid hydroxyethylamide (LSH), sometimes referred to as "organic LSD", occurs in the fresh seeds of morning glories, Hawaiian baby woodrose, and similar plants. It is not stable and tends to decomposes into lysergic acid amide and acetaldehyde over time. It is believed by some to be the primary alkaloid responsible for the psychedelic effects of fresh seeds. At one time it was believed that lysergic acid amide, also found in such seeds, was responsible for the psychedelic effects of the seeds, but lysergic acid amide has since been classified as a sedative with only mild psychoactivity, and isn't potent enough to cause the psychoactivity experienced from the levels of seeds commonly ingested for psychedelic effects.


LSH is believed by some to have psychedelic properties similar to LSD. Animal tests also suggest that it has actions similar to LSD.[1]

Tests in man have not been documented.

The seeds of morning glories, Hawaiian baby woodrose, and similar plants are often ingested for their psychedelic effects. Such seeds contain a large amount of lysergic acid amide, and when fresh also contain large amounts of LSH. It's often been noted that fresh seeds have the most psychedelic effects, while old seeds are mostly sedating. The LSH in the seeds decomposes to lysergic acid amide over time. Lysergic acid amide is classified as a sedative. Sedatives typically reduce the effects of psychedelics. It's been noted that there are currently no known published psychedelic effects caused by lysergic acid amide, only sedation. Therefor something other than lysergic acid amide must be the source of the psychedelic effects of such seeds. Of all the various alkaloids present in these seeds LSH is the most closely related to LSD in it's chemical structure. While some of the other alkaloids in these seeds have been documented to have psychedelic effects at high doses, they do not occur in large enough quantities to have much of an effect at the seed doses ingested for psychedelic effects. These facts seem to point to LSH as being the main active psychedelic compound.

Adduct of LSA and Acetaldehyde

LSA Acetaldehyde LSH
LSA.png Acetaldehyde.png LSH.png

LSH is an adduct of lysergic acid amide and acetaldehyde.

LSH is not stable and is said to decompose back into lysergic acid amide and acetaldehyde under certain conditions. LSA can be prepared by decomposing the related adducts ergotoxine or ergotinine in alcoholic potassium hydroxide.[2] It's theoretically possible that LSH can also be decomposed to LSA in alcoholic potassium hydroxide.

Adducts of LSA (Anecdotal)


Note: this data is believed to be completely accurate, stemming from work originally published by Albert Hofmann, and later further refined by other individuals from various online forums (references are unfortunately not available).

As with LSD, one of the most stable forms of lysergic acid hydroxyethylamide is it's tartrate form.

Lysergic acid hydroxyethylamide freebase is notoriously unstable. In the freebase form, it decomposes in the presence of UV light and oxygen. In water it will rapidly hydrolyze into acetaldehyde and the potent sedative lysergic acid amide.

Lysergic acid hydroxyethylamide in freebase form can be dissolved in solutions where the pH is 3-4, such as white wine or sherry wine without hydrolyzing into acetaldehyde and lysergic acid amide. Dissolving lysergic acid hydroxyethylamide in white wine or sherry wine produces lysergic acid hydroxyethylamide tartrate which is one of the most stable forms of lysergic acid hydroxyethylamide. The wine will also protect it from oxygen exposure to a certain degree, and if the wine is kept in an amber bottle, UV light exposure will be greatly reduced.

Lysergic acid hydroxyethylamide tartrate is more heat stable than lysergic acid amide tartrate is. Lysergic acid amide tartrate will decompose and become inactive when boiled in water for only a few minutes. Lysergic acid hydroxyethylamide tartrate can withstand being boiled in water for several minutes with almost no decomposition occurring.


The intravenous LD50 is approximately 150mg/kg for mice and 0.75 mg/kg for rabbits. Before death, the mice showed periodic convulsions of a clonic type, erection of the hairs and excitability.[1]

Animal Tests

At doses of 50-100 mg/kg it cause mice stand upright and press on each other's noses and chatter their teeth.[1]

In rabbits, injection into the ear vein in doses of 0.1-1mg/kg caused dilatation of the pupil, excitability or convulsions of a clinic type. The rabbit ears became pale and cold with intense vasoconstirction.[1]

The respiration of rabbits and cats was depressed by small doses. Cats seemed to be less resistant than rabbits. In cats, 0.01mg/kg caused broncho-constriction and contractions of the nictitating membrane of long duration.[1]

Because of marked alteration in behavior in animal tests it was concluded to possibly have LSD-like psychedelic activity in animals.[1]

Chemical Properties

Synonyms: LSH; LAH; lysergic acid alpha-hydroxyethylamide; Lysergic acid methyl carbinolamide; N-(alpha-Hydroxyethyl)lysergamide; D-lysergic acid methyl carbinolamide; D-Lysergic acid α-hydroxyethylamide
PubChem Compound ID: 134553
CAS Number: 3343-15-5
Molecular Weight: 311.37824 [g/mol]
Molecular Formula: C18H21N3O2
XLogP3: 1.9
IUPAC Name: (6aR,9R)-N-(1-hydroxyethyl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
InChI: InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10?,12-,16-/m1/s1
Canonical SMILES: CC(NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C)O
Isomeric SMILES: CC(NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C)O
Solubility: LSH maleate is soluble in aqueous solutions.[1]
Boiling Point: Unknown
Software Predicted Boiling Point: 620.2±55.0 °C1

See Also

Some Pharmacological Actions of D-lysergic acid methyl carbinaolamide; Glasser, A; Nature. 1961 Jan 28;189:313-4. PubMed PMID: 13705953
2. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine
Sydney Smith and Geoffrey Millward Timmis J. Chem. Soc., 1932, Pages 763-766. DOI: 10.1039/JR9320000763
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License