Indolylpropylaminopentane

IPAP
Clinical data
Other names	IPAP; 1-(Indol-3-yl)-2-propylaminopentane; α,N-Dipropyltryptamine, α,N-DPT
Drug class	Monoaminergic activity enhancer
Identifiers
	IUPAC name 1-(1H-indol-3-yl)-N-propylpentan-2-amine;
CAS Number	220491-98-5 ;
PubChem CID	22007056;
Chemical and physical data
Formula	C16H24N2
Molar mass	244.382 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(CC1=CNC2=CC=CC=C21)NCCC;
	InChI InChI=1S/C16H24N2/c1-3-7-14(17-10-4-2)11-13-12-18-16-9-6-5-8-15(13)16/h5-6,8-9,12,14,17-18H,3-4,7,10-11H2,1-2H3; Key:OQTWGSLVDILQOQ-UHFFFAOYSA-N;

Indolylpropylaminopentane (IPAP), also known as α,N-dipropyltryptamine (α,N-DPT), is a monoaminergic activity enhancer (MAE) that is closely related to benzofuranylpropylaminopentane (BPAP) and phenylpropylaminopentane (PPAP).^[1]^[2]^[3]^[4]^[5] It is a tryptamine derivative and the corresponding analogue of PPAP and BPAP with an indole ring instead of a benzene ring or benzofuran ring, respectively.^[3] IPAP is also a positional isomer of N,N-dipropyltryptamine (N,N-DPT).^[6]

Quick facts Clinical data, Other names ...

MAEs are agents that enhance the action potential-mediated release of monoamine neurotransmitters.^[7]^[8]^[9] IPAP is a MAE of serotonin, norepinephrine, and dopamine.^[3]^[2] However, IPAP acts preferentially as a MAE of serotonin and is about 10-fold more potent in enhancing serotonin than in enhancing norepinephrine or dopamine.^[3]^[2] This is in contrast to BPAP, which is of similar potency as a MAE of serotonin and the catecholamines.^[3]^[2] It is also in contrast to PPAP and selegiline, which act exclusively as catecholaminergic activity enhancers (CAEs) and do not enhance serotonin.^[7]^[8]^[9] Hence, IPAP is a representative selective serotonergic activity enhancer (SAE) at lower doses.^[3]^[2]

IPAP is more potent as a MAE than PPAP and selegiline but is less potent than BPAP.^[3]^[2] As with BPAP and PPAP, the negative enantiomer (i.e., R(–)-IPAP) is more biologically active as a MAE and is often the employed compound.^[3] The effects of MAEs appear to be mediated by intracellular TAAR1 agonism coupled with uptake by monoamine transporters into monoaminergic neurons.^[3]^[4]

In contrast to amphetamines, IPAP has no classical monoamine releasing agent actions.^[1]^[3] It is a weak MAO-A inhibitor similarly to BPAP.^[1]^[2]^[5]

IPAP was first described in the scientific literature in 2001, following BPAP in 1999.^[2]^[8]^[10] It was discovered by József Knoll and colleagues.^[2]^[8]^[10]

See also