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 ;
	(verify)

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.^[5]^[6]^[7]

^ Erowid Morning Glory Basics, Erowid.org, retrieved 2012-02-03
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
^ Smith S, Timmis GM (1932). "98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine". Journal of the Chemical Society (Resumed): 763. doi:10.1039/jr9320000763.
^ Perrine DM (2000). "Mixing the Kykeon" (PDF). ELEUSIS: Journal of Psychoactive Plants and Compounds. New Series 4: 9. Archived from the original (PDF) on 2019-07-20. Retrieved 2008-05-05.
^ Alexander Shulgin, "#26. LSD-25", TiHKAL, Erowid.org, retrieved 2012-02-03
^ Hofmann A (2009). LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science (4th ed.). MAPS.org. ISBN 978-0979862229.

[1] Erowid Morning Glory Basics, Erowid.org, retrieved 2012-02-03

[2] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[3] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[4] Smith S, Timmis GM (1932). "98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine". Journal of the Chemical Society (Resumed): 763. doi:10.1039/jr9320000763.

[5] Perrine DM (2000). "Mixing the Kykeon" (PDF). ELEUSIS: Journal of Psychoactive Plants and Compounds. New Series 4: 9. Archived from the original (PDF) on 2019-07-20. Retrieved 2008-05-05.

[erowid3-6] Alexander Shulgin, "#26. LSD-25", TiHKAL, Erowid.org, retrieved 2012-02-03

[LSD_my_problem_child4-7] Hofmann A (2009). LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science (4th ed.). MAPS.org. ISBN 978-0979862229.

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Clinical data


Other names	LSA; d-Lysergic acid amide; d-Lysergamide; Ergine; LA-111
Pregnancy category	X^[1]
Routes of administration	Oral, intramuscular injection
ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)^[2] DE: NpSG (Industrial and scientific use only) UK: Class A US: Schedule III Illegal in France^[3]
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name (8β)-9,10-didehydro-6-methyl- ergoline-8-carboxamide
CAS Number	478-94-4^Y
PubChem CID	442072
ChemSpider	390611^Y
UNII	073830XH10
ChEBI	CHEBI:4819^Y
ChEMBL	ChEMBL227213^Y
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^[4]
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^Y Key:GENAHGKEFJLNJB-QMTHXVAHSA-N^Y
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