| D-Lysergic acid | | Chemical name | 6-Methyl-9,10-didehydro-
ergoline-8-carboxylic acid
or
7-methyl-4,6,6a,7,8,9-
hexahydro-indolo[4,3-fg]
quinoline-9-carboxylic acid | | Chemical formula | C16H16N2O2 | | Molecular mass | 268.31 g/mol | | Melting point | 238 - 240 °C | | pI | ? | | Properties | Prisms from methanol, dec 242°. | | CAS number | 82-58-6, 478-95-5,
6915-32-8, 23953-76-6,
68985-97-7, 68985-98-8 | | SMILES | O=[C@](O)[C@H]1CN(C)
[C@](C2=C1)([H])CC3=C
NC4=C3C2=CC=C4 |
 | 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 some plants. Amides of lysergic acid, commonly called lysergamides, are widely used as pharmaceuticals and as psychedelic drugs (LSD). Lysergic acid is usually produced by hydrolysis of lysergamides, but can also be synthesized in the laboratory by a complex total synthesis. Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at 2 mmHg) forms anhydrous lysergic acid. Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at carbon atom 8 close to the carboxy group is called isolysergic acid. Inversion at carbon 5 close to the nitrogen atom leads to L-lysergic acid and L-isolysergic acid, respectively. Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances [1]. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...
The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...
The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...
The isoelectric point sucks (pI) is the pH at which a molecule carries no net electrical charge. ...
A property is an intrinsic or extrinsic quality of an object—where an object may be of any differing nature, depending on the context and field — be it computing, philosophy, etc. ...
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ...
Image File history File links Download high-resolution version (867x1060, 5 KB) Description: Chemical structure of lysergic acid. ...
Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ...
Species About 50, including: Claviceps africanum Claviceps fusiformis Claviceps paspali Claviceps purpurea Ergot is the common name of a fungus in the genus Claviceps. ...
Amide functional group In chemistry, an amide is one of two kinds of compounds: - the organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group (pictured to the right); or - a particular kind of nitrogen anion. ...
Oral medication A medication is a licenced drug taken to cure or reduce symptoms of an illness or medical condition. ...
Certain drugs can affect the subjective qualities of perception, thought or emotion, resulting in altered interpretations of sensory input, alternate states of consciousness, or hallucinations. ...
For other uses, see LSD (disambiguation). ...
Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ...
A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available (petrochemical) precursors. ...
The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ...
A stereocenter in organic chemistry generally refers to a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to it. ...
In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ...
A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ...
General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ...
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances Opened for signature December 20, 1988[1] at Vienna Entered into force November 11, 1990[2] Conditions for entry into force 20 ratifications Parties 170[3] The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and...
See also
Chemical structure of ergine Ergine, also known as d-lysergic acid amide, LSA, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi. ...
Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ...
For other uses, see LSD (disambiguation). ...
| Ergolines edit | | | Lysergic acid derivatives | | Bromocriptine, Cabergoline, Ergine, Ergonovine, Ergotamine, Lysergic acid, Lysergol, d-Lysergic acid hydroxyethylamide, Lisuride, Methergine, Methysergide, Pergolide Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ...
Bromocriptine is an ergoline derivative dopamine agonist that is used in the treatment of pituitary tumors and Parkinsons disease. ...
// Introduction and Phrmacology Cabergoline (brand names Dostinex® and Cabaser®), an ergot-derivative, is a potent dopamine receptor agonist on D2-Receptors. ...
Chemical structure of ergine Ergine, also known as d-lysergic acid amide, LSA, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi. ...
Ergonovine, also known as ergometrine, d-lysergic acid beta-propanolamide, is one of primary ergot alkaloids and an alkaloid of many species of morning glory, too. ...
Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ...
Chemical structure of lysergol Lysergol, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi. ...
Chemical structure of d-lysergic acid α-hydroxyethylamide D-lysergic acid α-hydroxyethylamide, also known as d-lysergic acid methyl carbinolamide, is a psychedelic alkaloid of the ergoline family, and occurs in various species of vines of the Convolvulaceae and some species of fungi. ...
Lisuride (brand name in Germany Dopergin) is an antiparkinson drug of the iso-ergoline class, chemically related to the dopaminergic ergoline parkinson drugs. ...
Methergine is a blood vessel constrictor most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. ...
Methysergide (UML-491) is a prescription drug used for prophylaxis of migraine headaches and is sold under the brand names Sansert® and Deseril® in 2mg dosages. ...
Pergolide is an ergoline-based dopamine receptor agonist used for the treatment of Parkinsons disease. ...
| | Hallucinogenic lysergamides | | AL-LAD, ALD-52, BU-LAD, CYP-LAD, DAL, DAM-57, Ergonovine, ETH-LAD, LAE-32, LSD, LPD-824, LSM-775, Methylergonovine, MLD-41, PARGY-LAD, PRO-LAD Hallucinogenic drugs or hallucinogens are drugs that can alter sensory perceptions, elicit alternate states of consciousness, or cause hallucinations. ...
9,10-DIDEHYDRO-6-ALLYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (AL-LAD) is an analogue of LSD first made by Alexander Shulgin and reported in the book TIHKAL. AL-LAD is a hallucinogenic drug similar to LSD, and is around the same potency as LSD itself with an active dose...
ALD-52 or N-acetyl-LSD, is a chemical analogue of LSD-25 (D-Lysergic Acid Diethylamide), discovered by Albert Hofmann, but later just filed away. ...
9,10-DIDEHYDRO-6-BUTYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (BU-LAD) is an analogue of LSD first made by Alexander Shulgin and reported in the book TIHKAL. BU-LAD is a hallucinogenic drug similar to LSD, but is significantly less potent than LSD with a dose of 500 micrograms...
9,10-DIDEHYDRO-6-CYCLOPROPYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (CYP-LAD) is an analogue of LSD and presumably has similar effects. ...
N,N-Diallyllysergamide (DAL) As the tartrate salt, there is at best a touch of sparkle seen at 600 micrograms orally, but there is a sedation also reported. ...
N,N-Dimethyllysergamide (DAM-57) is a derivative of ergine. ...
Ergonovine, also known as ergometrine, d-lysergic acid beta-propanolamide, is one of primary ergot alkaloids and an alkaloid of many species of morning glory, too. ...
9,10-DIDEHYDRO-6-ETHYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (ETH-LAD) is an analogue of LSD first made by Alexander Shulgin and reported in the book TIHKAL. ETH-LAD is a hallucinogenic drug similar to LSD, and is slightly more potent than LSD itself with an active dose reported...
D-Lysergic Acid Ethylamide, (LAE-32) is a derivative of ergine. ...
For other uses, see LSD (disambiguation). ...
N-Pyrrolidyllysergamide (LPD-824) is a derivative of ergine. ...
N-Morpholinyllysergamide (LSM-775) is a derivative of ergine. ...
Methylergonovine, also known as methylergometrine, methylergobasin, and d-lysergic acid 1-butanolamide, is a synthetic analogue of ergonovine, a psychedelic alkaloid found in ergot, and many species of morning glory. ...
N1-Methyl-Lysergic Acid Diethylamide (MLD-41, 9,10-didehydro-N,N-diethyl-1,6-dimethyl-ergoline-8-beta-carboxamide) is a derivative of LSD. The 1-methyl homologue of LSD is has more of somatic than sensory effect, has fewer visuals and is less well accepted than LSD, with...
9,10-DIDEHYDRO-6-PROPYNYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (PARGY-LAD) is an analogue of LSD first made by Alexander Shulgin and reported in the book TIHKAL. PARGY-LAD is a hallucinogenic drug similar to LSD, but is slightly less potent than LSD with a dose of 160 micrograms...
9,10-DIDEHYDRO-6-PROPYL-N,N-DIETHYLERGOLINE-8b-CARBOXAMIDE (PRO-LAD) is an analogue of LSD first made by Alexander Shulgin and reported in the book TIHKAL. PRO-LAD is a hallucinogenic drug similar to LSD, and is around as potent as LSD itself with an active dose reported...
| | Other ergolines | | Ergoline Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ...
| | Natural sources | | Argyreia nervosa, Claviceps spp., Ipomoea tricolor, Ipomoea violacea, Rivea corymbosa Binomial name Argyreia nervosa (Burm. ...
Species About 50, including: Claviceps africanum Claviceps fusiformis Claviceps paspali Claviceps purpurea Ergot is the common name of a fungus in the genus Claviceps. ...
Binomial name Ipomoea tricolor Cav. ...
Binomial name Ipomoea violacea L. Ipomoea violacea, sometimes known as the Morning Glory, is a species of morning glory that occurs throughout the tropics. ...
Binomial name Rivea corymbosa (L.)Hallier f. ...
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