Propylamphetamine

Propylamphetamine (code name PAL-424; also known as N-propylamphetamine or NPA) is a psychostimulant of the amphetamine family which was never marketed. It was first developed in the 1970s, mainly for research into the metabolism of,^[1] and as a comparison tool to, other amphetamines.^[2]

Propylamphetamine

Clinical data
Other names	N-Propylamphetamine; NPA; PAL-424
ATC code	none
Legal status
Legal status	UK: Not controlled
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name N-(1-methyl-2-phenylethyl)propan-1-amine
CAS Number	51799-32-7 N
PubChem CID	103544
ChemSpider	11655332 Y
UNII	E52ZLB6J7C
CompTox Dashboard (EPA)	DTXSID30966120
ECHA InfoCard	100.215.934
Chemical and physical data
Formula	C12H19N
Molar mass	177.291 g·mol−1
3D model (JSmol)	Interactive image
SMILES NC(C)Cc1ccccc1CCC
InChI InChI=1S/C12H19N/c1-3-6-11-7-4-5-8-12(11)9-10(2)13/h4-5,7-8,10H,3,6,9,13H2,1-2H3 Y Key:VMVXCJCVBKWYTF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Propylamphetamine is inactive as a dopamine releasing agent in vitro and instead acts as a low-potency dopamine reuptake inhibitor with an IC₅₀Tooltip half-maximal inhibitory concentration of 1,013 nM.^[3] The drug can be N-dealkylated to form amphetamine (10–20% excreted in urine after 24 hours).^[4][5] A study in rats found propylamphetamine to be approximately 4-fold less potent than amphetamine.^[6][7]

Monoamine release of propylamphetamine 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	[3][8][9]
d-Amphetamine	6.6–10.2	5.8–24.8	698–1,765	[10][11][9][12]
d-Methamphetamine	12.3–14.3	8.5–40.4	736–1,292	[10][13][9][12]
Ethylamphetamine	ND	88.5	ND	[3]
d-Ethylamphetamine	28.8	44.1	333.0	[6][14]
Propylamphetamine	ND	RI (1,013)	ND	[3]
Butylamphetamine	ND	IA (>10,000)	ND	[3]
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: [15][16]

See also

• Methamphetamine
• Ethylamphetamine
• Isopropylamphetamine
• Butylamphetamine
• Phenylpropylaminopentane