Butylamphetamine

Last updated
Butylamphetamine
Butylamphetamine.svg
Clinical data
Other namesN-Butylamphetamine; N-(n-Butyl)amphetamine; NBA; PAL-90; 1-Phenyl-2-butylaminopropane; N-Butyl-α-methylphenethylamine
Identifiers
  • N-(1-phenylpropan-2-yl)butan-1-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C13H21N
Molar mass 191.318 g·mol−1
3D model (JSmol)
  • CCCCNC(C)CC1=CC=CC=C1
  • InChI=1S/C13H21N/c1-3-4-10-14-12(2)11-13-8-6-5-7-9-13/h5-9,12,14H,3-4,10-11H2,1-2H3
  • Key:VIAVBPFRYASSKF-UHFFFAOYSA-N

Butylamphetamine (code name PAL-90; also known as N-butylamphetamine or NBA) is a psychostimulant of the substituted amphetamine family which was never marketed. [1] [2] [3]

It is the N-butyl analogue of amphetamine [1] and is approximately 6-fold less potent than amphetamine in rats. [2] [3] The drug has been found to be inactive as a dopamine reuptake inhibitor or releasing agent (IC50 Tooltip half-maximal inhibitory concentration and EC50 Tooltip half-maximal effective concentration > 10,000 nM, respectively). [1] 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. [1] [2] [3]

The pharmacokinetics of butylamphetamine have been studied in humans. [4] [5] It can be metabolized by CYP2D6 via ring hydroxylation similarly to amphetamine. [6] [7] In addition, butylamphetamine can be N-dealkylated into amphetamine (6–9% excreted in urine after 24 hours). [5]

See also

Related Research Articles

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Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

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<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

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<span class="mw-page-title-main">Etilamfetamine</span> Chemical compound

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<span class="mw-page-title-main">Propylamphetamine</span> Chemical compound

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<span class="mw-page-title-main">Methedrone</span> Chemical compound of the cathinone class

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<i>para</i>-Chloroamphetamine Chemical compound

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<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

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<span class="mw-page-title-main">4-Methylamphetamine</span> Stimulant and anorectic drug of the amphetamine class

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DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

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<span class="mw-page-title-main">3-Fluorophenmetrazine</span> Stimulant designer drug

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<span class="mw-page-title-main">Phenacylamine</span> Phenethylamine derivative

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References

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