γ-Hydroxybutyraldehyde
Names
Preferred IUPAC name
Other names
GHBAL, γ-hydroxybutaldehyde, γ-hydroxybutanal
Identifiers
ChemSpider
ECHA InfoCard
100.042.900
UNII
InChI=1S/C4H8O2/c5-3-1-2-4-6/h3,6H,1-2,4H2
Key: PIAOXUVIBAKVSP-UHFFFAOYSA-N
InChI=1/C4H8O2/c5-3-1-2-4-6/h3,6H,1-2,4H2
Key: PIAOXUVIBAKVSP-UHFFFAOYAV
Properties
C 4 H 8 O 2
Molar mass
88.106 g·mol−1
Appearance
colorless liquid
Density
1.109 g/cm3 (at 12 °C)
Boiling point
65–68 °C (149–154 °F; 338–341 K) 10 Torr
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
γ-Hydroxybutyraldehyde is the organic compound with the formula HOCH2 CH2 CH2 CHO. It is a colorless liquid. The compound occurs in nature and is produced commercially.[ 1]
It is a chemical intermediate in the biosynthesis of the neurotransmitter γ-hydroxybutyric acid (GHB) from 1,4-butanediol (1,4-BD).[ 2] Like 1,4-BD, it also behaves as a prodrug to GHB when taken exogenously . However, as with all aliphatic aldehydes , γ-hydroxybutaldehyde is caustic and is strong-smelling and foul-tasting; thus, actual ingestion of this compound is likely to be unpleasant and result in severe nausea and vomiting .
Metabolic pathway of GHB.
Receptor (ligands )
GHBR Tooltip GHB receptor GABAB Tooltip γ-Aminobutyric acid B receptor
Transporter (blockers )
MCTs Tooltip Monocarboxylate transporters SMCTs Tooltip Sodium-coupled monocarboxylate transporters VIATT Tooltip Vesicular inhibitory amino acid transporter
Enzyme (inhibitors )
SSR Tooltip Succinic semialdehyde reductase GHBDH Tooltip 4-Hydroxybutyrate dehydrogenase HOT Tooltip Hydroxyacid-oxoacid transhydrogenase ADH Tooltip Alcohol dehydrogenase ALDH Tooltip Aldehyde dehydrogenase
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