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]

Butylamphetamine

Clinical data
Other names	N-Butylamphetamine; N-(n-Butyl)amphetamine; NBA; PAL-90; 1-Phenyl-2-butylaminopropane; N-Butyl-α-methylphenethylamine
Identifiers
IUPAC name N-(1-phenylpropan-2-yl)butan-1-amine
CAS Number	51799-33-8
PubChem CID	94547
ChemSpider	85320
ChEMBL	ChEMBL1907545
Chemical and physical data
Formula	C13H21N
Molar mass	191.318 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCNC(C)CC1=CC=CC=C1
InChI 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

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]

Monoamine release of butylamphetamine and related agents (EC₅₀Tooltip Half maximal effective concentration, nM)

Compound	NETooltip Norepinephrine	DATooltip Dopamine	5-HTTooltip Serotonin	Ref
Phenethylamine	10.9	39.5	>10,000	[1][4][5]
d-Amphetamine	6.6–10.2	5.8–24.8	698–1,765	[6][7][5][8]
d-Methamphetamine	12.3–14.3	8.5–40.4	736–1,292	[6][9][5][8]
Ethylamphetamine	ND	88.5	ND	[1]
d-Ethylamphetamine	28.8	44.1	333.0	[2][10]
Propylamphetamine	ND	RI (1,013)	ND	[1]
Butylamphetamine	ND	IA (>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]

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

• Methamphetamine
• Ethylamphetamine
• Propylamphetamine
• Isopropylamphetamine