Butylamphetamine (code name PAL-90; also known as N-butylamphetamine or NBA) is a psychostimulant of the substituted amphetamine family which was never marketed.
It is the N-butyl analogue of amphetamine and is approximately 6-fold less potent than amphetamine in rats. The drug has been found to be inactive as a dopamine reuptake inhibitor or releasing agent ( and > 10,000nM, respectively). With regard to structure–activity relationships, the potency of N-substituted amphetamine derivatives decreases with increasing chain length in terms of both in vitro and in vivo activity.
+ Compound Ref Phenethylamine 10.9 39.5 >10,000 d-Amphetamine 6.6–10.2 5.8–24.8 698–1,765 d-Methamphetamine 12.3–14.3 8.5–40.4 736–1,292 Ethylamphetamine 88.5 d-Ethylamphetamine 28.8 44.1 333.0 Propylamphetamine (1,013) Butylamphetamine (>10,000) Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:
The pharmacokinetics of butylamphetamine have been studied in humans. It can be metabolized by CYP2D6 via ring hydroxylation similarly to amphetamine. In addition, butylamphetamine can be N-dealkylated into amphetamine (6–9% excreted in urine after 24hours).
See also Methamphetamine Ethylamphetamine Propylamphetamine Isopropylamphetamine
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