From Wikipedia, the free encyclopedia
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]
Occurrence
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.
See also
References
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