3-Pyrrolylpropylamine

3-Pyrrolylpropylamine, also known as α-methyl-3-pyrrolylethylamine, is a chemical compound of the arylalkylamine family.^[1] It is the analogue of the serotonergic psychedelic α-methyltryptamine (AMT) in which the benzene component of the indole ring has been removed.^[1]

3-Pyrrolylpropylamine

Clinical data
Other names	α-Methyl-3-pyrrolylethylamine; 3-Pyrrolepropylamine
Identifiers
IUPAC name 1-(1H-pyrrol-3-yl)propan-2-amine
CAS Number	128600-49-7
PubChem CID	13437356
ChemSpider	23182624
ChEMBL	ChEMBL328939
Chemical and physical data
Formula	C7H12N2
Molar mass	124.187 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CNC=C1)N
InChI InChI=1S/C7H12N2/c1-6(8)4-7-2-3-9-5-7/h2-3,5-6,9H,4,8H2,1H3 Key:XMTHAWZPEGHZPK-UHFFFAOYSA-N

In contrast to tryptamines like AMT, 3-pyrrolylpropylamine does not bind to the serotonin 5-HT_1A or 5-HT_2A receptors (K_i = >10,000 nM).^[1] These findings suggest that the benzene part of the indole ring is required for significant binding to serotonin receptors and by extension psychedelic activity.^[1] The activities of 3-pyrrolylpropylamine at other targets, such as the monoamine transporters, were not reported.^[1]

3-Pyrrolylpropylamine was first described in the scientific literature by at least 1990.^[1]

See also

• 3-Pyrrolylethylamine
• 2-Pyrrolylethylamine