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SCH-50911

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SCH-50911

Names

Preferred IUPAC name

2-[(2S)-5,5-Dimethylmorpholin-2-yl]acetic acid

Identifiers

160415-07-6^Y

3D model (JSmol)

Interactive image

4470917^Y

1075

5311429

Q5MMG73452^Y

CompTox Dashboard (EPA)

DTXSID701336120 DTXSID0045670, DTXSID701336120

InChI=1S/C8H15NO3/c1-8(2)5-12-6(4-9-8)3-7(10)11/h6,9H,3-5H2,1-2H3,(H,10,11)/t6-/m0/s1^Y

Key: SEYCKMQSPUVYEF-LURJTMIESA-N^Y

InChI=1/C8H15NO3/c1-8(2)5-12-6(4-9-8)3-7(10)11/h6,9H,3-5H2,1-2H3,(H,10,11)/t6-/m0/s1

Key: SEYCKMQSPUVYEF-LURJTMIEBV

O=C(O)C[C@@H]1OCC(NC1)(C)C

Properties

Chemical formula

C₈H₁₅NO₃

173.21 g·mol⁻¹

154.5 to 157 °C (310.1 to 314.6 °F; 427.6 to 430.1 K) (hydrochloride)

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

SCH-50911 is a selective GABA_B antagonist.^[1] Its main applications are in pharmacology research.

SCH-50911 also acts as an anticonvulsant under normal conditions. SCH-50911 induces acute withdrawal syndrome in GHB-dependent rats, similar to the delirium tremens seen in human alcohol withdrawal, and can precipitate convulsions in GHB-dependent animals.^[2]

References[edit]

^ Blythin DJ, Kuo SC, Shue HJ, McPhail AT, Chapman RW, Kreutner W, et al. (July 1996). "Substituted morpholine-2S-acetic acid derivatives: Sch 50911 and related compounds as novel GABAB antagonists". Bioorganic & Medicinal Chemistry Letters. 6 (13): 1529–34. doi:10.1016/S0960-894X(96)00267-3.

^ Quang LS, Colombo G, Lobina C, Maccioni P, Orru A, Gessa GL, et al. (August 2006). "Evaluation for the withdrawal syndrome from gamma-hydroxybutyric acid (GHB), gamma-butyrolactone (GBL), and 1,4-butanediol (1,4-BD) in different rat lines". Annals of the New York Academy of Sciences. 1074 (1): 545–58. Bibcode:2006NYASA1074..545Q. doi:10.1196/annals.1369.055. PMID 17105952. S2CID 86383425.

GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Agonists: (+)-Catechin

Barbiturates (e.g., phenobarbital)

Dihydromuscimol

Gaboxadol (THIP)

Homotaurine (tramiprosate, 3-APS)

Isonipecotic acid

Lignans (e.g., honokiol)

Neuroactive steroids (e.g., allopregnanolone)

Terpenoids (e.g., borneol)

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., drinking alcohol, 2M2B)
Anabolic steroids
Avermectins (e.g., ivermectin)
Barbiturates (e.g., phenobarbital)
Benzodiazepines (e.g., diazepam)
Bromide compounds (e.g., potassium bromide)
Carbamates (e.g., meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid)
Flavonoids (e.g., apigenin, hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate)
Kava constituents (e.g., kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone, cholesterol, THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol)
Phenytoin
Piperidinediones (e.g., glutethimide)
Propanidid
Pyrazolopyridines (e.g., etazolate)
Quinazolinones (e.g., methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g., baicalin)
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g., valerenic acid)
Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Agonists: BL-1020

Homohypotaurine

N⁴-Chloroacetylcytosine arabinoside

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

GABA_BTooltip γ-Aminobutyric acid B receptor

Agonists: 1,4-Butanediol

4-Fluorophenibut

Arbaclofen placarbil

Negative modulators: Compound 14

See also

Receptor/signaling modulators

GABA_A receptor positive modulators

GABA metabolism/transport modulators

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