Lysergic Acid Hydroxyethylamide
LSH.png

Lysergic acid hydroxyethylamide (LSH) occurs in the fresh seeds of morning glories and similar plants. It is not stable and tends to decomposes into lysergic acid amide and acetaldehyde over time.


Psychoactivity

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

Tests in man have not been documented.

Its decomposition product lysergic acid amide is classified as a sedative.


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)


Toxicity

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
InChIKey: WYTJZJPVCDWOOI-WPJLSRQMSA-N
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]


See Also


Bibliography
1. Glasser, A;
Some Pharmacological Actions of D-lysergic acid methyl carbinaolamide; 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
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