Lysergic acid hydroxyethylamide

LSH
Clinical data
Other names	LAH; LSH; Lysergic acid N-(α-hydroxyethyl)amide; ᴅ-Lysergic acid methyl carbinolamide; N-(1-Hydroxyethyl)lysergamide; N(HOE)-LA; Lysergic acid-α-hydroxyethylamide
Legal status
Legal status	Illegal in France;
Identifiers
	IUPAC name 9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide;
CAS Number	3343-15-5 ;
PubChem CID	134553;
ChemSpider	27470958 ;
CompTox Dashboard (EPA)	DTXSID10955057 ;
ECHA InfoCard	100.020.079
Chemical and physical data
Formula	C18H21N3O2
Molar mass	311.385 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H](NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C)O;
	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+/m0/s1 ; Key:WYTJZJPVCDWOOI-KANYHAFZSA-N ;
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Lysergic acid hydroxyethylamide (LSH or LAH), also known as lysergic acid N-(α-hydroxyethyl)amide, is an ergoamide and an ergoline. It is perhaps the main constituent of the parasitic fungus, Claviceps paspali; and found in trace amounts in Claviceps purpurea. C. paspali and C. purpurea are ergot-spreading fungi. Periglandula, Clavicipitacepus fungi, are permanently symbiotically connected to an estimated 450 species of Convolvulaceae and thus generate LAH in some of them (42 generate ergolines, by Eckart Eich's review). The most well-known ones are Ipomoea tricolor (“morning glory”), Turbina corymbosa (coaxihuitl), and Argyreia nervosa (Hawaiian baby woodrose). LAH is structurally similar to ergonovine, which is also known as lysergic acid hydroxymethylethylamide.

The more well-known analog, lysergic acid amide (syn. ergine), is more prominent in analytical results because LAH easily decomposes to ergine. Ergine is only present because of the decomposition of LAH (and lysergic acid hydroxymethylethylamide and ergopeptines or their ergopeptam precursors); it is not generated. Indeed, a 2016 analysis found that fresher I. tricolor seeds contained more LAH than the other two batches analyzed (another interesting finding is that penniclavine was the predominant ergoline.)