Chemistry:Lysergol

Lysergol

Names
IUPAC name (6-Methyl-9,10-didehydroergolin-8β-yl)methanol
Systematic IUPAC name [(6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol
Identifiers
CAS Number	1413-67-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:60528 Y
ChEMBL	ChEMBL39947 Y
ChemSpider	14267 Y
IUPHAR/BPS	123
PubChem CID	14987
UNII	NTR684Z1AZ Y
InChI InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1 Y Key: BIXJFIJYBLJTMK-MEBBXXQBSA-N Y
SMILES OC[C@@H]3/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
Properties
Chemical formula	C16H18N2O
Molar mass	254.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. Lysergol is not a controlled substance in the USA. Its possession and sale is also legal under the U.S. Federal Analog Act because it does not have a known pharmacological action or a precursor relationship to LSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines (e.g., nicergoline).

Lysergol can be synthesised using a tandem reaction to construct the piperidine skeleton and a rhodium-catalyzed [3 + 2] annulation in the late-stage indole formation.

See also

• Lysergic acid
• Ipomoea tricolor

External links

• Hoffman, A. Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico Bulletin on Narcotics 1971 1 3
• Mixing the kykeon -- P. Webster, D. M. Perrine & C.A.P. Ruck
• TiHKAL (A & A Shulgin) #26
• Erowid's LSA Vault