Lysergol

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Lysergol
Lysergol.svg
Names
Preferred IUPAC name
[(6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.113 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: BIXJFIJYBLJTMK-MEBBXXQBSA-N Yes check.svgY
  • OC[C@@H]3/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
Properties
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).
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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 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).

Contents

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]

See also

Related Research Articles

Controlled Substances Act United States drug-regulating law

The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States Congress as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970 and signed into law by President Richard Nixon. The Act also served as the national implementing legislation for the Single Convention on Narcotic Drugs.

Convolvulaceae Family of flowering plants

Convolvulaceae, known commonly as the bindweed or morning glory family, is a family of about 60 genera and more than 1,650 species of mostly herbaceous vines, but also trees, shrubs and herbs, and also including the sweet potato and a few other food tubers.

Morning glory Common name for more than 1,000 species of flowering plants in the family Convolvulaceae

Morning glory is the common name for over 1,000 species of flowering plants in the family Convolvulaceae, whose current taxonomy and systematics are in flux. Morning glory species belong to many genera, some of which are:

Ergine Chemical compound

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 the dominant alkaloid present in the seeds.

Ergoline Chemical compound

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

Lysergic acid Precursor for a range of ergoline alkaloids produced by the ergot fungus

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Turbina corymbosa (ololiuhqui), Argyreia nervosa, and Ipomoea tricolor.

<i>Ipomoea</i> Genus of flowering plants

Ipomoea is the largest genus in the flowering plant family Convolvulaceae, with over 600 species. It is a large and diverse group, with common names including morning glory, water convolvulus or kangkung, sweet potato, bindweed, moonflower, etc.

<i>Ipomoea tricolor</i> Species of plant

Ipomoea tricolor, the Mexican morning glory or just morning glory, is a species of flowering plant in the family Convolvulaceae, native to the New World tropics, and widely cultivated and naturalised elsewhere. It is an herbaceous annual or perennial twining liana growing to 2–4 m (7–13 ft) tall. The leaves are spirally arranged, 3–7 cm (1–3 in) long with a 1.5–6 cm long petiole. The flowers are trumpet-shaped, 4–9 cm (2–4 in) in diameter, most commonly blue with a white to golden yellow centre.

<i>Argyreia nervosa</i> Species of plant

Argyreia nervosa is a perennial climbing vine native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa, and the Caribbean. Though it can be invasive, it is often prized for its aesthetic and medicinal value. Common names include Hawaiian baby woodrose, adhoguda अधोगुडा or vidhara विधारा (Sanskrit), elephant creeper and woolly morning glory. Its seeds are known for their powerful entheogenic properties, greater or similar to those of Ipomoea species, with users reporting significant psychedelic and spiritual experiences. The two botanical varieties are A. n. var. nervosa described here, and A. n. var. speciosa, which are used in Ayurvedic medicine for their medicinal value.

<i>Ipomoea aquatica</i> Species of plant

Ipomoea aquatica, most widely known as kangkong or water spinach, is a semi-aquatic, tropical plant grown as a vegetable for its tender shoots. I. aquatica is generally believed to have been first domesticated in Southeast Asia. It is widely cultivated in Southeast Asia, East Asia, and South Asia. It grows abundantly near waterways and requires little to no care.

<i>Ipomoea alba</i> Species of plant

Ipomoea alba, sometimes called the tropical white morning-glory or moonflower or moon vine, is a species of night-blooming morning glory, native to tropical and subtropical regions of North and South America, from Argentina to northern Mexico, Arizona, Florida and the West Indies. Though formerly classified as genus Calonyction, species aculeatum, it is now properly assigned to genus Ipomoea, subgenus Quamoclit, section Calonyction.

<i>Ipomoea purpurea</i> Species of plant

Ipomoea purpurea, the common morning-glory, tall morning-glory, or purple morning glory, is a species in the genus Ipomoea, native to Mexico and Central America.

Lysergic acid hydroxyethylamide Chemical compound

D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is an alkaloid of the ergoline family, believed to be present in small amounts in various species in the Convolvulaceae, as well as some species of fungi.

<i>Ipomoea quamoclit</i> Species of plant in the family Convolvulaceae

Ipomoea quamoclit, commonly known as cypress vine, cypress vine morning glory, cardinal creeper, cardinal vine, star glory, star of Bethlehem or hummingbird vine, is a species of vine in the family Convolvulaceae native to tropical regions of the New World and naturalized elsewhere in the tropics.

<i>Ipomoea violacea</i> Species of flowering plant

Ipomoea violacea is a perennial species of Ipomoea that occurs throughout the world with the exception of the European continent. It is most commonly called beach moonflower or sea moonflower as the flowers open at night.

<i>Ipomoea pes-caprae</i> Species of flowering plant

Ipomoea pes-caprae, also known as bayhops, bay-hops, beach morning glory or goat's foot, is a common pantropical creeping vine belonging to the family Convolvulaceae. It grows on the upper parts of beaches and endures salted air. It is one of the most common and most widely distributed salt tolerant plants and provides one of the best known examples of oceanic dispersal. Its seeds float and are unaffected by salt water.

<i>Ipomoea cairica</i> Species of vine

Ipomoea cairica is a vining, herbaceous, perennial plant with palmate leaves and large, showy white to lavender flowers. A species of morning glory, it has many common names, including mile-a-minute vine, Messina creeper, Cairo morning glory, coast morning glory and railroad creeper. The species name cairica translates to "from Cairo", the city where this species was first collected.

<i>Ipomoea tuberculata</i> Species of flowering plant

Ipomoea tuberculata is a flowering plant species in the bindweed family (Convolvulaceae). It belongs to the morning glory genus, Ipomoea.

<i>Ipomoea lobata</i> Species of flowering plant

Ipomoea lobata, the fire vine, firecracker vine or Spanish flag, is a species of flowering plant in the family Convolvulaceae, native to Mexico and Brazil.

<i>Ipomoea indica</i> Species of flowering plant

Ipomoea indica is a species of flowering plant in the family Convolvulaceae, known by several common names, including blue morning glory, oceanblue morning glory, koali awa, and blue dawn flower. It bears heart-shaped or 3-lobed leaves and purple or blue funnel-shaped flowers 6–8 cm (2–3 in) in diameter, from spring to autumn. The flowers produced by the plant are hermaphroditic. This plant has gained the Royal Horticultural Society's Award of Garden Merit.

References

  1. Yuan, Haosen; Guo, Zhixian; Luo, Tuoping (2017). "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Organic Letters. doi:10.1021/acs.orglett.6b03779. ISSN   1523-7060.