5-HO-DPT

5-HO-DPT, also known as 5-hydroxy-N,N-dipropyltryptamine, as well as N,N-dipropylserotonin (DiPS or NDPS), is a serotonin receptor modulator of the tryptamine and 5-hydroxytryptamine families.^[1] It is the N,N-dipropyl derivative of serotonin (5-hydroxytryptamine; 5-HT).^[1]

5-HO-DPT

Clinical data
Other names	5-Hydroxy-N,N-dipropyltryptamine; N,N-Dipropylserotonin; N,N-Di-n-propylserotonin; DiPS; NDPS
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 3-[2-(dipropylamino)ethyl]-1H-indol-5-ol
CAS Number	36288-75-2
PubChem CID	169764
ChemSpider	148461
ChEMBL	ChEMBL141706
CompTox Dashboard (EPA)	DTXSID80189827
Chemical and physical data
Formula	C16H24N2O
Molar mass	260.381 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)CCC1=CNC2=C1C=C(C=C2)O
InChI InChI=1S/C16H24N2O/c1-3-8-18(9-4-2)10-7-13-12-17-16-6-5-14(19)11-15(13)16/h5-6,11-12,17,19H,3-4,7-10H2,1-2H3 Key:CWMOGUBWVJQDSL-UHFFFAOYSA-N

Pharmacology

The drug shows affinity for the serotonin 5-HT_1A receptor (K_i = 7.1 nM), the serotonin 5-HT_1B receptor (K_i = 4,300 nM), and the serotonin 5-HT₂ receptor (K_i = 1.0–450 nM).^[1] 5-HO-DPT was not tested itself, but its O-methyl ether 5-MeO-DPT fully substituted for the psychedelic drug DOM in rodent drug discrimination tests and partially substituted for 8-OH-DPAT in these tests followed by behavioral disruption at higher doses.^[1] 5-Hydroxytryptamines like bufotenin (5-HO-DMT) are known to be hydrophilic and peripherally selective, in turn resulting in difficulty crossing the blood–brain barrier and exerting central effects,^[1] but 5-HO-DPT is notable in having much greater lipophilicity in comparison to bufotenin owing to its propyl groups (predicted log P = 3.0 and 1.2, respectively).^[2][3]

History

5-HO-DPT was first described in the scientific literature by Richard Glennon and colleagues by 1988.^[1]

See also

• Substituted tryptamine
• Bufotenin (5-HO-DMT)
• 5-HO-DET
• 5-HO-DiPT
• 5-MeO-DPT