Chemistry:Gamma-Hydroxybutyraldehyde
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Names | |
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Preferred IUPAC name
4-Hydroxybutanal | |
Other names
GHBAL, γ-hydroxybutaldehyde, γ-hydroxybutanal
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
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Properties | |
C4H8O2 | |
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). | |
Infobox references | |
γ-Hydroxybutyraldehyde is the organic compound with the formula HOCH2CH2CH2CHO. 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.
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. Lippincott Williams & Wilkins. pp. 413–. ISBN 978-1-60913-345-0. https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA413.
{{Navbox
| name = Neurotransmitter metabolism intermediates | title = Neurotransmitter metabolic intermediates | state = autocollapse| | listclass = hlist
| group1 = catecholamines | list1 = {{Navbox|child
| group1 = Anabolism
(tyrosine→epinephrine) | list1 =
- Tyrosine → Levodopa → [[Chemistry:Dop[[Chemistry:Dopamine → Norepinephrine|Norepinephrine]] → Epinephrine
| group2 = Catabolism/
metabolites
| list2 =
dopamine: | |
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norepinephrine: | |
epinephrine: |
}}
| group3 = tryptophan→serotonin| list3 =
anabolism: | |
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catabolism: |
| group4 = serotonin→melatonin | list4 =
}}
{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;
| group1 = Ionotropic | list1 = {{Navbox|subgroup | groupstyle = text-align:center | groupwidth = 5em
| group1 = GABAA | list1 =
- Agonists: (+)-Catechin
- Bamaluzole
- Barbiturates (e.g., phenobarbital)
- BL-1020
- DAVA
- Dihydromuscimol
- GABA
- Gabamide
- GABOB
- Gaboxadol (THIP)
- Homotaurine (tramiprosate, 3-APS)
- Ibotenic acid
- iso-THAZ
- iso-THIP
- Isoguvacine
- Isomuscimol
- Isonipecotic acid
- Kojic amine
- Lignans (e.g., honokiol)
- Methylglyoxal
- Monastrol
- Muscimol
- Nefiracetam
- Neuroactive steroids (e.g., allopregnanolone)
- Org 20599
- PF-6372865
- Phenibut
- Picamilon
- P4S
- Progabide
- Propofol
- Quisqualamine
- SL-75102
- TACA
- TAMP
- Terpenoids (e.g., borneol)
- Thiomuscimol
- Tolgabide
- ZAPA
- Positive modulators (abridged; see here for a full list): α-EMTBL
- Alcohols (e.g., ethanol)
- 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)<!--PMID: 9776662-->
- Lanthanum
- Loreclezole
- Monastrol
- Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
- Niacin
- Nicotinamide (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, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)
- Antagonists: Bicuculline
- Coriamyrtin
- Dihydrosecurinine
- Gabazine (SR-95531)
- Hydrastine
- Hyenachin (mellitoxin)
- PHP-501
- Pitrazepin
- Securinine
- Sinomenine
- SR-42641
- SR-95103
- Thiocolchicoside
- Tutin
- Negative modulators: 1,3M1B
- 3M2B
- 11-Ketoprogesterone
- 17-Phenylandrostenol
- 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 (123I)
- IPTBO
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Leptazol
- Lindane
- MaxiPost
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], 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
| group2 = GABAA-ρ | list2 =
- Agonists: BL-1020
- CACA
- CAMP
- Homohypotaurine
- GABA
- GABOB
- Ibotenic acid
- Isoguvacine
- Muscimol
- N4-Chloroacetylcytosine arabinoside
- Picamilon
- Progabide
- TACA
- TAMP
- Thiomuscimol
- Tolgabide
- Positive modulators: Allopregnanolone
- Alphaxolone
- ATHDOC
- Lanthanides
- Antagonists: (S)-2-MeGABA
- (S)-4-ACPBPA
- (S)-4-ACPCA
- 2-MeTACA
- 3-APMPA
- 4-ACPAM
- 4-GBA
- cis-3-ACPBPA
- CGP-36742 (SGS-742)
- DAVA
- Gabazine (SR-95531)
- Gaboxadol (THIP)
- I4AA
- Isonipecotic acid
- Loreclezole
- P4MPA
- P4S
- SKF-97541
- SR-95318
- SR-95813
- TPMPA
- trans-3-ACPBPA
- ZAPA
- Negative modulators: 5α-Dihydroprogesterone
- Bilobalide
- Loreclezole
- Picrotoxin (picrotin, picrotoxinin)
- Pregnanolone
- ROD-188
- THDOC
- Zinc
}}
| group2 = Metabotropic| list2 =
| below =
- See also
- Receptor/signaling modulators
- GABAA receptor positive modulators
- GABA metabolism/transport modulators
}}
![]() | Original source: https://en.wikipedia.org/wiki/Gamma-Hydroxybutyraldehyde.
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