Butylamphetamine

Amphetamine derivative and stimulant From Wikipedia, the free encyclopedia

Butylamphetamine

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]

Quick Facts Clinical data, Other names ...
Butylamphetamine
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
FormulaC13H21N
Molar mass191.318 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
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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 (IC50Tooltip half-maximal inhibitory concentration and EC50Tooltip 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]

More information Compound, NETooltip Norepinephrine ...
Monoamine release of butylamphetamine and related agents (EC50Tooltip Half maximal effective concentration, nM)
CompoundNETooltip NorepinephrineDATooltip Dopamine5-HTTooltip SerotoninRef
Phenethylamine10.939.5>10,000[1][4][5]
d-Amphetamine6.6–10.25.8–24.8698–1,765[6][7][5][8]
d-Methamphetamine12.3–14.38.5–40.4736–1,292[6][9][5][8]
EthylamphetamineND88.5ND[1]
  d-Ethylamphetamine28.844.1333.0[2][10]
PropylamphetamineNDRI (1,013)ND[1]
ButylamphetamineNDIA (>10,000)ND[1]
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: [11][12]
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The pharmacokinetics of butylamphetamine have been studied in humans.[13][14] It can be metabolized by CYP2D6 via ring hydroxylation similarly to amphetamine.[15][16] In addition, butylamphetamine can be N-dealkylated into amphetamine (6–9% excreted in urine after 24 hours).[14]

See also

References

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