N-Hydroxyamphetamine

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]

Other namesNOHA; HOT-A; AMPH-OH

Drug classStimulant

ATC code

None

CAS Number

63-90-1
4490-17-9 (hydrochloride)

Quick facts Clinical data, Other names ...

N-Hydroxyamphetamine
Clinical data

Other names	NOHA; HOT-A; AMPH-OH
Drug class	Stimulant
ATC code	None
Identifiers
IUPAC name N-(1-phenylpropan-2-yl)hydroxylamine
CAS Number	63-90-1 4490-17-9 (hydrochloride)
PubChem CID	65546
ChemSpider	58990
UNII	A2AXB2C6CQ
Chemical and physical data
Formula	C₉H₁₃NO
Molar mass	151.209 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=CC=C1)NO
InChI InChI=1S/C9H13NO/c1-8(10-11)7-9-5-3-2-4-6-9/h2-6,8,10-11H,7H2,1H3 Key:LPZRPPBVFGJUOJ-UHFFFAOYSA-N

References

[1]
Nichols DE (1994). "Medicinal Chemistry and Structure-Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9. 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]
Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Research Monograph. 94: 43–67. PMID 2575229. 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]
Glennon RA, Yousif M, Patrick G (March 1988). "Stimulus properties of 1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) analogs". Pharmacology, Biochemistry, and Behavior. 29 (3): 443–449. 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]
Abbruscato TJ, Trippier PC (October 2018). "DARK Classics in Chemical Neuroscience: Methamphetamine". ACS Chemical Neuroscience. 9 (10): 2373–2378. 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]
Beckett AH, al-Sarraj S (April 1973). "The identification, properties and analysis of N-hydroxyamphetamine--a metabolite of amphetamine". The Journal of Pharmacy and Pharmacology. 25 (4): 329–334. doi:10.1111/j.2042-7158.1973.tb10017.x. PMID 4146687.
[6]
King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
[7]
King LA (1996). "Designer drugs related to amphetamine (1990-1996)". J Clan Lab Invest Chem Assoc. 6 (3): 15–16.

N-Hydroxyamphetamine

See also

References

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