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Propylamphetamine

Chemical compound

Field	Value
Verifiedfields	changed
verifiedrevid	464217299
IUPAC_name	N-(1-methyl-2-phenylethyl)propan-1-amine
image	N-Propylamphetamine.svg
image_class	skin-invert-image
image2	Propylamphetamine molecule ball.png
image_class2	bg-transparent
alt2	Ball-and-stick model of the propylamphetamine molecule
legal_UK	Not controlled
metabolism	Hepatic
excretion	Renal
CAS_number_Ref
CAS_number	51799-32-7
UNII_Ref
UNII	E52ZLB6J7C
ATC_prefix	none
PubChem	103544
ChemSpiderID_Ref
ChemSpiderID	11655332
synonyms	N-Propylamphetamine; NPA; PAL-424
C	12	H=19	N=1
smiles	NC(C)Cc1ccccc1CCC
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	VMVXCJCVBKWYTF-UHFFFAOYSA-N

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, and as a comparison tool to, other amphetamines.

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

Compound	Ref
Phenethylamine	10.9
d-Amphetamine	6.6–10.2
d-Methamphetamine	12.3–14.3
Ethylamphetamine	ND
d-Ethylamphetamine	28.8
Propylamphetamine	ND
Butylamphetamine	ND
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:

References

(1983). "Amphetamine in rat brain after intraperitoneal injection of N-alkylated analogues". Progress in Neuro-Psychopharmacology & Biological Psychiatry.
(October 1995). "Evaluation of internal standards for the analysis of amphetamine and methamphetamine". Journal of Analytical Toxicology.
(February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend.
(October 1973). "The effect of N-alkyl chain length of stereochemistry on the absorption, metabolism and during excretion of N-alkylamphetamines in man". J Pharm Pharmacol.
(November 1976). "In vitro metabolism of 1-phenyl-2-(n-propylamino) propane (N-propylamphetamine) by rat liver homogenates". J Pharm Pharmacol.
(March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology.
(December 1980). "Structure-activity relationships among some d-N-alkylated amphetamines". Pharmacology, Biochemistry, and Behavior.
Forsyth, Andrea N. (22 May 2012). "Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines".
(July 2008). "Dopamine Transporters: Chemistry, Biology and Pharmacology". Wiley.
(January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
(March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
(1999). "Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc".
(April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
Nicole, Lauren. (2022). "In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones".
(October 2003). "Monoamine transporters and psychostimulant drugs". European Journal of Pharmacology.
(2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry.

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designer-prodrugs norepinephrine-dopamine-releasing-agents substituted-amphetamines

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