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Names | |
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Preferred IUPAC name 4-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanamido]butanoic acid | |
Identifiers | |
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3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID | |
UNII |
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CompTox Dashboard (EPA) | |
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Properties | |
C10H19NO5 | |
Molar mass | 233.264 g·mol−1 |
Related compounds | |
Related alkanoic acids | |
Related compounds | Panthenol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Hopantenic acid (homopantothenic acid), also known as N-pantoyl-GABA, is a central nervous system depressant. Formulated as the calcium salt, it is used as a pharmaceutical drug in the Russian Federation for a variety of neurological, psychological and psychiatric conditions and sold as Pantogam (Russian : Пантогам). [1]
Hopantenic acid is a homologue of pantothenic acid. While pantothenic acid is the amide of D-pantoate and β-alanine, hopantenic acid is the amide of D-pantoate and γ-aminobutyric acid (GABA). This change leads to an additional CH2 in the molecule. [2]
Pantothenic acid (vitamin B5) is a B vitamin and an essential nutrient. All animals need pantothenic acid in order to synthesize coenzyme A (CoA)—essential for metabolizing fatty acid—and to synthesize and metabolize proteins, carbohydrates, and fats.
β-Alanine is a naturally occurring beta amino acid, which is an amino acid in which the amino group is attached to the β-carbon instead of the more usual α-carbon for alanine (α-alanine). The IUPAC name for β-alanine is 3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.
Ovation Pharmaceuticals is an American manufacturer and distributor of pharmaceuticals products. It was founded in 2000 by Jeffrey Aronin and is headquartered in Deerfield, Illinois. A major office is also located near Lebanon, New Jersey. Ovation is a privately held corporation based on a business model of acquiring mature but under-promoted pharmaceuticals, as well as pharmaceutical candidates which are far along the development and FDA certification processes. Since 2009, the company has been wholly owned by the Danish pharmaceutical company Lundbeck.
Muscimol is one of the principal psychoactive constituents of Amanita muscaria and related species of mushroom. Muscimol is a potent and selective orthosteric agonist for the GABAA receptors and displays sedative-hypnotic, depressant and hallucinogenic psychoactivity. This colorless or white solid is classified as an isoxazole.
Aniracetam, also known as N-anisoyl-2-pyrrolidinone, is a racetam which is sold in Europe as a prescription drug. It is not approved by the Food and Drug Administration for use in the United States as a prescription medication or dietary supplement. Despite the FDA's lack of approval, the drug is readily available over-the-counter in misbranded dietary supplements.
Bumetanide, sold under the brand name Bumex among others, is a medication used to treat swelling and high blood pressure. This includes swelling as a result of heart failure, liver failure, or kidney problems. It may work for swelling when other medications have not. For high blood pressure it is not a preferred treatment. It is taken by mouth, or by injection into a vein or muscle. Effects generally begin within an hour and lasts for about six hours.
Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.
Phenibut, sold under the brand names Anvifen, Fenibut, and Noofen among others, is a central nervous system depressant with anxiolytic effects, and is used to treat anxiety, insomnia, and for a variety of other indications. It is usually taken by mouth as a tablet, but may be given intravenously.
Picamilon is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969 and further studied in both Russia and Japan as a prodrug of GABA.
Gusperimus is an immunosuppressive drug. It is a derivative of the naturally occurring HSP70 inhibitor spergualin, and inhibits the interleukin-2-stimulated maturation of T cells to the S and G2/M phases and the polarization of the T cells into IFN-gamma-secreting Th1 effector T cells, resulting in the inhibition of growth of activated naive CD4 T cells.
Pazinaclone (DN-2327) is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Some other cyclopyrrolone drugs include zopiclone and eszopiclone.
In enzymology, a pantoate 4-dehydrogenase (EC 1.1.1.106) is an enzyme that catalyzes the chemical reaction
γ-Amino-β-hydroxybutyric acid (GABOB), also known as β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), and sold under the brand name Gamibetal among others, is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico. It is a GABA analogue, or an analogue of the neurotransmitter γ-aminobutyric acid (GABA), and has been found to be an endogenous metabolite of GABA.
In enzymology, a pantothenase (EC 3.5.1.22) is an enzyme that catalyzes the chemical reaction
Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s, but mostly publicised through research conducted by the team led by David E. Nichols at Purdue University. It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single sec-butyl group, joined at the 2-position. It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination assays, with the (R) isomer having an ED50 of 33nmol/kg for producing drug-appropriate responding, vs 48nmol/kg for LSD itself. The corresponding (R)-2-pentyl analogue has higher binding affinity for the 5-HT1A and 5-HT2A receptors, but is less potent in producing drug-appropriate responding, suggesting that the butyl compound has a higher efficacy at the receptor target. The drug discrimination assay for LSD in rats involves both 5-HT1A and 5-HT2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT1A agonist, it is slightly less potent as a 5-HT2A agonist, and so would probably be slightly less potent than LSD as a hallucinogen in humans. The main use for this drug has been in studies of the binding site at the 5-HT2A receptor through which LSD exerts most of its pharmacological effects, with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as lysergic acid 2,4-dimethylazetidide (LSZ).
BNC210 is an anxiolytic drug that acts via negative allosteric modulation of the α7-nicotinic acetylcholine receptor, by Bionomics Limited. It is currently being investigated for the treatment of post traumatic stress disorder. The drug has demonstrated clinically significant anxiety reduction in both animal models and in Phase I trials.
Pantoic acid is the alpha hydroxy acid with the formula HOCH2C(CH3)2CH(OH)CO2H. The compound is almost always encountered in a biological context, as an aqueous solution of its conjugate base pantoate HOCH2C(CH3)2CH(OH)CO2-. The amide of pantoic acid with β-alanine is pantothenic acid (vitamin B5), a component of coenzyme A.
Phenylpiracetam hydrazide, also known as fonturacetam hydrazide, is a racetam that is a derivative of phenylpiracetam in which the amide group is replaced with a hydrazide group. It was first reported by a Russian research group in 1980 as part of a series of chemical compounds investigated as anticonvulsants. In an electroshock test it was found to have an ED50 of 310 mg/kg.
A GABA analogue is a compound which is an analogue or derivative of the neurotransmitter gamma-Aminobutyric acid (GABA).
Tolibut, also known as 3-(p-tolyl)-4-aminobutyric acid (or β-(4-methylphenyl)-GABA), is drug that was developed in Russia. It is an analogue of γ-aminobutyric acid (GABA) (that is, a GABA analogue) and is the 4-methyl analogue of phenibut, and is also an analogue of baclofen where the 4-chloro substitution has been replaced with a 4-methyl substitution. Tolibut has been described as possessing analgesic, tranquilizing, and neuroprotective properties. It is not fully clear as to whether the drug was ever approved or used medically in Russia, though it may have been.