γ-Hydroxybutyraldehyde
Names
Preferred IUPAC name
Other names
GHBAL, γ-hydroxybutaldehyde, γ-hydroxybutanal
Identifiers
3D model (JSmol )
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
Chemical formula
C 4 H 8 O 2
Molar mass
−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).
Infobox references
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] 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 [ ]
^ Ahn, H. (1999). "Hydroformylation of olefins with formaldehyde in the presence of RhHCO(PPh3)3". Journal of Molecular Catalysis A: Chemical . 144 (2): 295–306. doi :10.1016/S1381-1169(99)00002-3 . ^ Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry ISBN 978-1-60913-345-0
Neurotransmitter metabolic intermediates
catecholamines
Anabolismtyrosine →epinephrine )
Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine Catabolism/
dopamine: norepinephrine: epinephrine:
tryptophan →serotonin
serotonin →melatonin
Receptor (ligands )
Transporter (blockers )
Enzyme (inhibitors )
SSR GHBDH
Enhancers: D -Glucuronic acid HOT ADH ALDH
Acetaldehyde Cimetidine Cyanamide Disulfiram Prunetin
See also
Receptor/signaling modulators GABA receptor modulators Glutamate receptor modulators Glycine receptor modulators
Ionotropic
GABAA
Positive modulators (abridged; see here for a full list): 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 (e.g., sulfonmethane (sulfonal) )
Topiramate Valerian constituents (e.g., valerenic acid )Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )Negative modulators: 11-Ketoprogesterone 17-Phenylandrostenol α5IA (LS-193,268) Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO )BIDN Bilobalide Bupropion Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin DMCM EBOB FG-7142 (ZK-31906) (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 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 PWZ-029 Radequinil Ro 15-4513 Sarmazenil Suritozole TB-21007 TBPS Terbequinil TETS Thujone Zinc ZK-93426 GABAA -ρ
Metabotropic
See also
Receptor/signaling modulators GABAA receptor positive modulators GABA metabolism/transport modulators
