Chemistry:N-Hydroxyamphetamine

From HandWiki

N-Hydroxyamphetamine
Clinical data
Other namesNOHA; HOT-A; AMPH-OH
Drug classStimulant
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)

N-Hydroxyamphetamine (NOHA), also known as AMPH-OH, is a stimulant drug of the amphetamine family.[1][2][3] It is the N-hydroxy derivative of amphetamine and has similar potency in terms of stimulant-like activity in animals.[1][3] NOHA is a known metabolite of amphetamine[4][5] and may be a prodrug of amphetamine.[1][2] It has been encountered as a novel designer drug.[6][7]

See also

References

  1. ↑ 1.0 1.1 1.2 "Medicinal Chemistry and Structure-Activity Relationships". Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. 1994. pp. 3–41. ISBN 978-0-12-173375-9. https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3. "In drug discrimination tests in rats, both N-ethyl and N-hydroxy amphetamine gave complete substitution in (+)-amphetamine-trained rats (Glennon et al., 1988). [...] Note that tertiary amine congeners may be N-dealkylated in vivo to generate secondary amines, which are inherently more potent. [...] In a study of the analgesic and psychopharmacological effects of a series of N-alkylated MDA derivatives, Braun et al. (1980) reported that only the N-methyl, N-ethyl, and N-hydroxy compounds were active. However, evidence suggests that the N-hydroxy compound may be reduced metabolically to MDA, a process known to occur with the N-hydroxy derivative of PCA (Fuller et al., 1974)." 
  2. ↑ 2.0 2.1 "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Research Monograph 94: 43–67. 1989. PMID 2575229. https://web.archive.org/web/20250715154848/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54. "The latter compound, the N-hydroxy, in all probability serves merely as a prodrug for MDA, being metabolically reduced to the primary amine, as has been observed for para-chloramphetamine (PCA) (Fuller et al. 1974). [...] The N-hydroxy analog of AMPH (i.e., N-OH AMPH), a metabolite of AMPH, also produces AMPH-like effects and is about twice as potent as AMPH (table 2). [...] Although N-hydroxy-p-chloroamphetamine did deplete serotonin, it was metabolized rapidly and almost quantitatively to p-chloroamphetamine (Fuller et al. 1974).". 
  3. ↑ 3.0 3.1 "Stimulus properties of 1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) analogs". Pharmacology, Biochemistry, and Behavior 29 (3): 443–449. March 1988. doi:10.1016/0091-3057(88)90001-9. PMID 2896360. "Indeed, others have previously reported that N-OH amphetamine produces amphetamine-like behavioral effects and that, in some assays, it is at least as potent as amphetamine [2,18].". 
  4. ↑ "DARK Classics in Chemical Neuroscience: Methamphetamine". ACS Chemical Neuroscience 9 (10): 2373–2378. October 2018. doi:10.1021/acschemneuro.8b00123. PMID 29602278. "Amphetamine undergoes further metabolic changes, resulting in the production of para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31". 
  5. ↑ "The identification, properties and analysis of N-hydroxyamphetamine--a metabolite of amphetamine". The Journal of Pharmacy and Pharmacology 25 (4): 329–334. April 1973. doi:10.1111/j.2042-7158.1973.tb10017.x. PMID 4146687. 
  6. ↑ "New phenethylamines in Europe". Drug Testing and Analysis 6 (7–8): 808–818. 2014. doi:10.1002/dta.1570. PMID 24574327. 
  7. ↑ "Designer drugs related to amphetamine (1990-1996).". J Clan Lab Invest Chem Assoc 6 (3): 15–16. 1996. https://isomerdesign.com/bitnest/external/JCLIC/6.3.15-16. 



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