γ-Hydroxyvaleric acid

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γ-Hydroxyvaleric acid
Clinical data

Other names	γ-Hydroxyvaleric acid GVB
Legal status
Legal status	US: DEA considers GHV a controlled substance analogue.^[1] In general: uncontrolled
Identifiers
IUPAC name 4-Hydroxyvaleric acid
CAS Number	13532-37-1
PubChem CID	114539
ChemSpider	102591
UNII	58B139Q3RL
CompTox Dashboard (EPA)	DTXSID60928958
ECHA InfoCard	100.033.516
Chemical and physical data
Formula	C₅H₁₀O₃
Molar mass	118.132 g·mol⁻¹

γ-Hydroxyvaleric acid (GHV), also known as 4-methyl-GHB, is a designer drug related to γ-hydroxybutyric acid (GHB). It is sometimes seen on the grey market as a legal alternative to GHB, but with lower potency and higher toxicity,^[2] properties which have tended to limit its recreational use.^[3]

γ-Valerolactone (GVL) acts as a prodrug to GHV, analogously to how γ-butyrolactone (GBL) is a prodrug to GHB.^[4]

References

^ "GHB and Analogues: Fast Facts". National Drug Intelligence Center. January 1, 2006. Archived from the original on July 26, 2023. Retrieved July 5, 2023.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
^ Carter LP, Chen W, Wu H, Mehta AK, Hernandez RJ, Ticku MK, et al. (April 2005). "Comparison of the behavioral effects of gamma-hydroxybutyric acid (GHB) and its 4-methyl-substituted analog, gamma-hydroxyvaleric acid (GHV)". Drug and Alcohol Dependence. 78 (1): 91–99. doi:10.1016/j.drugalcdep.2004.10.002. PMID 15769562.
^ Smith F (31 December 2004). Handbook of Forensic Drug Analysis. Academic Press. pp. 462–. ISBN 978-0-08-047289-8.
^ Andresen-Streichert H, Jungen H, Gehl A, Müller A, Iwersen-Bergmann S (May 2013). "Uptake of gamma-valerolactone--detection of gamma-hydroxyvaleric acid in human urine samples". Journal of Analytical Toxicology. 37 (4): 250–254. doi:10.1093/jat/bkt013. PMID 23486087.

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

GABA receptor modulators

Ionotropic

GABA_A

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
Beta-Alanine
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
L-838,417
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
4-PIOL
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

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 (¹²³I)
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

GABA_A-ρ

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

Metabotropic

GABA_B

Negative modulators: Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

GHB receptor modulators

Receptor
(ligands)

GHBR

Agonists: Main site: 1,4-BD
3-HPA
Aceburic acid (GHB acetate)
BDDA (DABD)
EAB
GBL
GCL
GHB
GHBAL
GHV (4-methyl-GHB)
GVL
HOCHCA
HOCPCA
MAB
NCS-356
NCS-435
Sodium oxybate
T-HCA (GHC)
THF
UMB58
UMB66
UMB68
UMB72
UMB73
UMB86; Positive allosteric modulators: (+)-Catechin
Monastrol

Antagonists: Main site: Gabazine (SR-95531)
NCS-382

Unknown/unsorted: Main site: 2-HPA
3-Methyl-GHB
3-Methyl-THCA
4-Benzyl-GHB
4-HPBA
4-Methyl-THCA
4-Phenyl-GHB
4-Phenyl-THCA
Amisulpride
azido-BnOPh-GHB
BnOPh-GHB
DHV
DVL
GTBL
Levosulpiride
NCS-400
Prochlorperazine
Sulpiride
Sultopride
UMB108
UMB109
UMB119

GABA_B

See here instead.

Transporter
(blockers)

MCTsTooltip Monocarboxylate transporters	α-Ketoisocaproate Acetoacetic acid AR-C155858 Atorvastatin Benzoic acid BHB Butyric acid CHCA DBDS DIDS Hexanoic acid Lactic acid Luteolin Niflumic acid NPPB Phenylpyruvic acid Phloretin Probenecid Pyruvic acid Quercetin Salicylic acid Simvastatin Sodium valproate Valproic acid
SMCTsTooltip Sodium-coupled monocarboxylate transporters	Benzoic acid BHB Butyric acid Fenoprofen Ibuprofen Ketoprofen Mesalazine (5-ASA) Naproxen Nicotinic acid Probenecid Propionic acid Pyruvic acid Salicyclic acid
VIATTTooltip Vesicular inhibitory amino acid transporter	β-Alanine Bafilomycin A1 Butyric acid Evans blue GABA Glycine Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme
(inhibitors)

SSRTooltip Succinic semialdehyde reductase	Quercetin
GHBDHTooltip 4-Hydroxybutyrate dehydrogenase	α-Ketoisocaproic acid Ethosuximide Phenylacetate Salicylic acid Valproic acid Enhancers: D-Glucuronic acid
HOTTooltip Hydroxyacid-oxoacid transhydrogenase	Cyanide Phenanthroline
ADHTooltip Alcohol dehydrogenase	Cimetidine Ethanol Fomepizole (4-methylpyrazole) Pyrazole
ALDHTooltip Aldehyde dehydrogenase	Acetaldehyde Cimetidine Cyanamide Disulfiram Prunetin

See also: Receptor/signaling modulators; GABA receptor modulators; Glutamate receptor modulators; Glycine receptor modulators

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See also

References