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Endogenous GABA precursor
N -Acetyl-γ-aminobutyric acid
Names
IUPAC name
4-acetamidobutanoic acid
Other names
N -Acetyl-GABA; N -Acetyl-4-aminobutyric acid
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.019.261
EC Number
KEGG
UNII
InChI=1S/C6H11NO3/c1-5(8)7-4-2-3-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
Key: UZTFMUBKZQVKLK-UHFFFAOYSA-N
Properties
C 6 H 11 N O 3
Molar mass
145.158 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
N -Acetyl-γ-aminobutyric acid (N -acetyl-GABA ), also known as N -acetyl-4-aminobutyric acid , is a metabolic intermediate in the biosynthesis of γ-aminobutyric acid (GABA) from putrescine .[ 1] [ 2] [ 3] [ 4] Other intermediates in this pathway include N -acetylputrescine and N -acetyl-γ-aminobutyraldehyde (N -acetyl-GABAL or N -acetyl-GABA aldehyde).[ 2] [ 3] [ 4] Enzymes mediating the transformations in this pathway include putrescine acetyltransferase (PAT), monoamine oxidase B (MAO-B), aldehyde dehydrogenase (ALDH), and an unknown deacetylase enzyme .[ 2] [ 3] [ 4] The pathway is a minor pathway in GABA synthesis compared to the main pathway in which GABA is synthesized from glutamate .[ 2] [ 3] [ 4] However, the pathway has been found to have an important physiological role in the brain, for instance in the production of GABA in the striatum and resultant inhibition of dopaminergic neurons in this brain area.[ 1] [ 4]
^ a b Nam MH, Sa M, Ju YH, Park MG, Lee CJ (April 2022). "Revisiting the Role of Astrocytic MAOB in Parkinson's Disease" . Int J Mol Sci . 23 (8): 4453. doi :10.3390/ijms23084453 . PMC 9028367 . PMID 35457272 .
^ a b c d Watanabe M, Maemura K, Kanbara K, Tamayama T, Hayasaki H (2002). "GABA and GABA Receptors in the Central Nervous System and Other Organs". A Survey of Cell Biology . International Review of Cytology. Vol. 213. pp. 1–47. doi :10.1016/s0074-7696(02)13011-7 . ISBN 978-0-12-364617-0 . PMID 11837891 .
^ a b c d Seiler N (June 2004). "Catabolism of polyamines". Amino Acids . 26 (3): 217–233. doi :10.1007/s00726-004-0070-z . PMID 15221502 .
^ a b c d e Cho HU, Kim S, Sim J, Yang S, An H, Nam MH, Jang DP, Lee CJ (July 2021). "Redefining differential roles of MAO-A in dopamine degradation and MAO-B in tonic GABA synthesis" . Exp Mol Med . 53 (7): 1148–1158. doi :10.1038/s12276-021-00646-3 . PMC 8333267 . PMID 34244591 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
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 )
Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins , cephalosporins , carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (TBPS , TBPO , IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g., fipronil )
Flavonoids (e.g., amentoflavone , oroxylin A )
Flumazenil
Fluoroquinolones (e.g., ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor