5-MeO-DPAC

5-MeO-DPAC, also known as 5-methoxy-3-(dipropylamino)chroman, is a potent and highly selective serotonin 5-HT_1A receptor full agonist related to 8-OH-DPAT. It is a derivative of 3-aminochroman, in which in the 5th position of the benzene ring there is a methoxy group, and in the 3rd position of dipropylamine.

Other names5-Methoxy-3-(dipropylamino)chroman; 5-Methoxy-3-(di-n-propylamino)chroman; 5-Methoxy-3,4-dihydro-N,N-dipropyl-2H-1-benzopyran-3-amine

Drug classSerotonin 5-HT_1A receptor agonist

ATC code

• None

Legal status

• Generally not controlled

Quick facts Clinical data, Other names ...

5-MeO-DPAC

Clinical data
Other names	5-Methoxy-3-(dipropylamino)chroman; 5-Methoxy-3-(di-n-propylamino)chroman; 5-Methoxy-3,4-dihydro-N,N-dipropyl-2H-1-benzopyran-3-amine
Drug class	Serotonin 5-HT1A receptor agonist
ATC code	None
Legal status
Legal status	Generally not controlled
Identifiers
IUPAC name 5-methoxy-N,N-dipropyl-3,4-dihydro-2H-chromen-3-amine
CAS Number	110927-00-9
PubChem CID	3082597
ChemSpider	2339997
ChEMBL	ChEMBL283606
CompTox Dashboard (EPA)	DTXSID90911898
Chemical and physical data
Formula	C16H25NO2
Molar mass	263.381 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)C1CC2=C(C=CC=C2OC)OC1
InChI InChI=1S/C16H25NO2/c1-4-9-17(10-5-2)13-11-14-15(18-3)7-6-8-16(14)19-12-13/h6-8,13H,4-5,9-12H2,1-3H3 Key:GOWYIQOIWRLZLO-UHFFFAOYSA-N

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The drug shows no affinity for other serotonin receptors or for the dopamine D₂ receptor. It acts at very low concentrations, albeit with lower potency than 8-OH-DPAT, and unlike 8-OH-DPAT, does not bind to presynaptic serotonin 5-HT_1A receptors in the striatum.^[1][2][3][4]

The mechanism of action of 5-MeO-DPAC is to reduce the synthesis and turnover of serotonin in the brain through selective activation of serotonin 5-HT_1A autoreceptors, which is mediated through a negative feedback system without a direct effect on striatal binding sites.^[5]

5-MeO-DPAC was first described in the scientific literature by 1987.^[1]