NCS-382

Names
IUPAC name

(2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene ethanoic acid

Identifiers

CAS Number

* 131733-92-1 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 4730868 N

MeSH | NCS-382

PubChem CID

* 5875451

UNII |

* 6QI4I5N23X Y

InChI

* InChI=1S/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+ N

Key: UADPGHINQMWEAG-CSKARUKUSA-N N

* InChI=1/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+

Key: UADPGHINQMWEAG-CSKARUKUBJ

SMILES

* c1ccc2c(c1)CCC/C(=C\C(=O)O)/C2O

Properties

Chemical formula

| C13H14O3
Molar mass | 218.248

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

NCS-382 is a moderately selective antagonist for the GHB receptor.[1][2] It blocks the effects of GHB in animals and has both anti-sedative and anticonvulsant effects.[3][4][5] It has been proposed as a treatment for GHB overdose in humans as well as the genetic metabolic disorder succinic semialdehyde dehydrogenase deficiency (SSADHD), but has never been developed for clinical use.[6]

## References

[edit]

1. ^ Castelli MP, Pibiri F, Carboni G, Piras AP (2004). "A review of pharmacology of NCS-382, a putative antagonist of gamma-hydroxybutyric acid (GHB) receptor". CNS Drug Reviews. 10 (3): 243–260. doi:10.1111/j.1527-3458.2004.tb00025.x. PMC 6741708. PMID 15492774.
2. ^ Ticku MK, Mehta AK (October 2008). "Characterization and pharmacology of the GHB receptor". Annals of the New York Academy of Sciences. 1139 (1): 374–385. Bibcode:2008NYASA1139..374T. doi:10.1196/annals.1432.048. PMID 18991884. S2CID 37091049.
3. ^ Maitre M, Hechler V, Vayer P, Gobaille S, Cash CD, Schmitt M, Bourguignon JJ (Nov 1990). "A specific gamma-hydroxybutyrate receptor ligand possesses both antagonistic and anticonvulsant properties". Journal of Pharmacology and Experimental Therapeutics. 255 (2): 657–63. PMID 2173754.
4. ^ Schmidt C, Gobaille S, Hechler V, Schmitt M, Bourguignon JJ, Maitre M (Oct 1991). "Anti-sedative and anti-cataleptic properties of NCS-382, a gamma-hydroxybutyrate receptor antagonist". European Journal of Pharmacology. 203 (3): 393–7. doi:10.1016/0014-2999(91)90896-X. PMID 1773824.
5. ^ Colombo G, Agabio R, Bourguignon J, Fadda F, Lobina C, Maitre M, Reali R, Schmitt M, Gessa GL (Sep 1995). "Blockade of the discriminative stimulus effects of gamma-hydroxybutyric acid (GHB) by the GHB receptor antagonist NCS-382". Physiology & Behavior. 58 (3): 587–590. doi:10.1016/0031-9384(95)00086-X. PMID 8587968. S2CID 45842160.
6. ^ Gupta M, Greven R, Jansen EE, Jakobs C, Hogema BM, Froestl W, Snead OC, Bartels H, Grompe M, Gibson KM (Jul 2002). "Therapeutic intervention in mice deficient for succinate semialdehyde dehydrogenase (gamma-hydroxybutyric aciduria)". Journal of Pharmacology and Experimental Therapeutics. 302 (1): 180–187. doi:10.1124/jpet.302.1.180. PMID 12065715. S2CID 24503217.

* v
* t
* e

GHB receptor modulators

Receptor
(ligands)|

| GHBRTooltip GHB receptor|

* Agonists: Main site: 1,4-BD
* 3-HPA
* Aceburic acid (GHB acetate)
* BDDA (DABD)
* EAB
* GBL
* GCL
* GHB
* GHBAL
* GHV (4-methyl-GHB)
* GVL
* HOCHCA
* HOCPCA
* MAB
* NCS-356
* NCS-435
* Sodium oxybate
* T-HCA (GHC)
* THF
* UMB58
* UMB66
* UMB68
* UMB72
* UMB73
* UMB86; Positive allosteric modulators: (+)-Catechin
* Monastrol

* Antagonists: Main site: Gabazine (SR-95531)
* NCS-382

* Unknown/unsorted: Main site: 2-HPA
* 3-Methyl-GHB
* 3-Methyl-THCA
* 4-Benzyl-GHB
* 4-HPBA
* 4-Methyl-THCA
* 4-Phenyl-GHB
* 4-Phenyl-THCA
* Amisulpride
* azido-BnOPh-GHB
* BnOPh-GHB
* DHV
* DVL
* GTBL
* Levosulpiride
* NCS-400
* Prochlorperazine
* Sulpiride
* Sultopride
* UMB108
* UMB109
* UMB119

|

GABABTooltip γ-Aminobutyric acid B receptor|

* See here instead.

Transporter
(blockers)|

| MCTsTooltip Monocarboxylate transporters|

* α-Ketoisocaproate
* Acetoacetic acid
* AR-C155858
* Atorvastatin
* Benzoic acid
* BHB
* Butyric acid
* CHCA
* DBDS
* DIDS
* Hexanoic acid
* Lactic acid
* Luteolin
* Niflumic acid
* NPPB
* Phenylpyruvic acid
* Phloretin
* Probenecid
* Pyruvic acid
* Quercetin
* Salicylic acid
* Simvastatin
* Sodium valproate
* Valproic acid

|

SMCTsTooltip Sodium-coupled monocarboxylate transporters|

* Benzoic acid
* BHB
* Butyric acid
* Fenoprofen
* Ibuprofen
* Ketoprofen
* Mesalazine (5-ASA)
* Naproxen
* Nicotinic acid
* Probenecid
* Propionic acid
* Pyruvic acid
* Salicyclic acid

VIATTTooltip Vesicular inhibitory amino acid transporter|

* β-Alanine
* Bafilomycin A1
* Butyric acid
* Evans blue
* GABA
* Glycine
* Nigericin
* Nipecotic acid
* Valinomycin
* Vigabatrin

Enzyme
(inhibitors)|

| SSRTooltip Succinic semialdehyde reductase|

* Quercetin

|

GHBDHTooltip 4-Hydroxybutyrate dehydrogenase|

* α-Ketoisocaproic acid
* Ethosuximide
* Phenylacetate
* Salicylic acid
* Valproic acid

* Enhancers: D-Glucuronic acid

HOTTooltip Hydroxyacid-oxoacid transhydrogenase|

* Cyanide
* Phenanthroline

ADHTooltip Alcohol dehydrogenase|

* Cimetidine
* Ethanol
* Fomepizole (4-methylpyrazole)
* Pyrazole

ALDHTooltip Aldehyde dehydrogenase|

* Acetaldehyde
* Cimetidine
* Cyanamide
* Disulfiram
* Prunetin

See also
Receptor/signaling modulators
GABA receptor modulators
Glutamate receptor modulators
Glycine receptor modulators
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[GHB]: γ-Hydroxybutyric acid
*[GHBR]: GHB receptor
*[GABAB]: γ-Aminobutyric acid B receptor
*[MCTs]: Monocarboxylate transporters
*[SMCTs]: Sodium-coupled monocarboxylate transporters
*[VIATT]: Vesicular inhibitory amino acid transporter
*[SSR]: Succinic semialdehyde reductase
*[GHBDH]: 4-Hydroxybutyrate dehydrogenase
*[HOT]: Hydroxyacid-oxoacid transhydrogenase
*[ADH]: Alcohol dehydrogenase
*[ALDH]: Aldehyde dehydrogenase