Ergine

Ergine
Clinical data
Other names	LSA; d-Lysergic acid amide; d-Lysergamide; Ergine; LA-111
Pregnancy; category	X;
Routes of; administration	Oral, intramuscular injection
ATC code	none;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: NpSG (Industrial and scientific use only); UK: Class A; US: Schedule III; Illegal in France;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	IUPAC name (8β)-9,10-didehydro-6-methyl-; ergoline-8-carboxamide;
CAS Number	478-94-4 ;
PubChem CID	442072;
ChemSpider	390611 ;
UNII	073830XH10;
ChEBI	CHEBI:4819 ;
ChEMBL	ChEMBL227213 ;
CompTox Dashboard (EPA)	DTXSID20893673 ;
ECHA InfoCard	100.006.841
Chemical and physical data
Formula	C16H17N3O
Molar mass	267.332 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	135 °C (275 °F) Decomposes
	SMILES O=C(N)[C@@H]1C=C2C3=CC=CC4=C3C(C[C@@]2([H])N(C1)C)=CN4;
	InChI InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1 ; Key:GENAHGKEFJLNJB-QMTHXVAHSA-N ;
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Ergine, also known as d-lysergic acid amide (LSA) and d-lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae and some species of fungi. The psychedelic properties in the seeds of ololiuhqui, Hawaiian baby woodrose and morning glories have been linked to ergine and/or isoergine, its epimer, as it is an alkaloid present in the seeds.

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