2-Oxo-LSD, also known as 2-oxy-LSD or 2-keto-LSD, or more fully as 2-oxo-2,3-dihydro-LSD, is a
lysergamide
Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedd ...
and
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
of the
psychedelic drug
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...
lysergic acid diethylamide
Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a Semisynthesis, semisynthetic, Hallucinogen, hallucinogenic compound derived from ergot, known for its powerful psychological effects and ...
(LSD).
It is a metabolite of LSD in both humans and various animal species,
although there are important differences in LSD
metabolism
Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
and relative proportions of metabolites between species.
Metabolism
It is formed directly from LSD in the body and is also possibly an
intermediate in the generation of LSD's major metabolite
2-oxo-3-hydroxy-LSD
2-Oxo-3-hydroxy-LSD, or 2-oxy-3-hydroxy-LSD, also known as O-H-LSD or OH-LSD, as well as more fully as 2-oxo-3-hydroxy-2,3-dihydro-LSD, is a lysergamide and the major metabolite of the psychedelic drug lysergic acid diethylamide (LSD). LSD is el ...
(O-H-LSD), which is present in
urine
Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...
at concentrations 4 to 40times those of LSD in humans.
However, O-H-LSD may also form from other metabolites, such as 3-hydroxy-LSD.
The specific
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s responsible for the generation of individual LSD metabolites like 2-oxo-LSD are largely unknown.
However, several
cytochrome P450
Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s were investigated and implicated in the formation of O-H-LSD in 2019.
Pharmacology
2-Oxo-LSD showed absence of various
pharmacological
Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...
effects in animals.
In contrast to LSD and certain other metabolites like
13-hydroxy-LSD
13-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is a major metabolite of LSD in rats and guinea pigs but a minor metabolite of LSD in monkeys and humans. Following its formation, 13-h ...
, 2-oxo-LSD failed to produce LSD-like
electroencephalogram
Electroencephalography (EEG)
is a method to record an electrogram of the spontaneous electrical activity of the brain. The bio signals detected by EEG have been shown to represent the postsynaptic potentials of pyramidal neurons in the neoc ...
(EEG) changes in rabbits.
2-Oxo-LSD at a dose of 300μg
orally produced no
psychoactive
A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...
effects in a human subject who had previously responded to 30μg LSD.
It was concluded that 2-oxo-LSD shows no LSD-like activity in the
central nervous system
The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...
and hence is inactive.
2-Oxo-LSD's
derivative
In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
O-H-LSD showed profound loss of activity at the
serotonin
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT2 receptors compared to LSD ''
in vitro
''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
''.
2-Oxo-LSD is said to readily enter the brain.
History
2-Oxo-LSD was first described in the
scientific literature
Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...
by Julius Axelrod and colleagues in 1957.
See also
*
Substituted lysergamide
Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embed ...
*
2-Oxo-3-hydroxy-LSD
2-Oxo-3-hydroxy-LSD, or 2-oxy-3-hydroxy-LSD, also known as O-H-LSD or OH-LSD, as well as more fully as 2-oxo-3-hydroxy-2,3-dihydro-LSD, is a lysergamide and the major metabolite of the psychedelic drug lysergic acid diethylamide (LSD). LSD is el ...
*
2,3-Dihydro-LSD
*
Nor-LSD
Nor-LSD, or norLSD, also known as ''N'',''N''-diethyl-6-norlysergamide or as ''N''-desmethyllysergic acid diethylamide (''N''-desmethyl-LSD), is a serotonin receptor modulator and putative psychedelic of the lysergamide family related to lyser ...
*
Lysergic acid ethyl-2-hydroxyethylamide (LEO)
*
Lysergic acid ethylamide (LAE)
*
13-Hydroxy-LSD
13-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is a major metabolite of LSD in rats and guinea pigs but a minor metabolite of LSD in monkeys and humans. Following its formation, 13-h ...
*
14-Hydroxy-LSD
14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate. ...
*
2-Bromo-LSD
*
2-Iodo-LSD
References
External links
2-Oxo-LSD-Isomer Design
Carboxamides
Diethylamino compounds
Human drug metabolites
Ketones
Lysergamides
{{Hallucinogen-stub