gamma-Hydroxyvaleric acid

*gamma*-Hydroxyvaleric acid
Clinical data
Other names	γ-Hydroxyvaleric acid; GVB
Legal status
Legal status	US: DEA considers GHV a controlled substance analogue.; 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.

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[1] "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)

[pmid15769562-2] 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.

[Smith2004-3] Smith F (31 December 2004). Handbook of Forensic Drug Analysis. Academic Press. pp. 462–. ISBN 978-0-08-047289-8.

[pmid23486087-4] 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.

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See also

References