Lysergic acid hydroxyethylamide information

Lysergic acid hydroxyethylamide

Clinical data
Other names	D-lysergic acid methyl carbinolamide
Legal status
Legal status	Illegal in France[1]
Identifiers
IUPAC name 9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
CAS Number	3343-15-5 Y
PubChem CID	134553
ChemSpider	27470958 N
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 N Key:WYTJZJPVCDWOOI-KANYHAFZSA-N N
NY (what is this?)  (verify)

D-Lysergic acid α-hydroxyethylamide (LSH, LAH), also known as D-lysergic acid methyl carbinolamide, is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea (Heavenly Blue Morning Glory), the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa (Hawaiian Baby Woodrose). Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh the seeds are. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH.