Lysergol
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| Template:Longitem | C16H18N2O |
| Molar mass | 254.33 g/mol |
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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 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.[1]
The binding of lysergol, as well as of isolysergol, to the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors has been described.[2][3]
In contrast to LSD and other lysergamides, lysergol is non-hallucinogenic in humans and is described as not contributing to the hallucinogenic effects of morning glory seeds.[4][5][6] It was inactive as a hallucinogen at doses of 2 to 8Script error: No such module "String".mg orally, up to more than 100Script error: No such module "String".times the effective dosage of LSD, but did produce light sedative-like effects at the 8Script error: No such module "String".mg dose.[4][6]
Lysergol is not a controlled substance in the United States. 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).
See also
References
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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
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