5-HO-DPT

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5-HO-DPT
File:Dipropylserotonin.svg
File:5-HO-DPT 3D.png
Clinical data
Other names5-Hydroxy-N,N-dipropyltryptamine; N,N-Dipropylserotonin; N,N-Di-n-propylserotonin; DiPS; NDPS
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-[2-(dipropylamino)ethyl]-1H-indol-5-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC16H24N2O
Molar mass260.381 g·mol−1
3D model (JSmol)
  • CCCN(CCC)CCC1=CNC2=C1C=C(C=C2)O
  • 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

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]

Pharmacology

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Pharmacodynamics

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The drug shows affinity for the serotonin 5-HT1A receptor (Ki = 7.1 nM), the serotonin 5-HT1B receptor (Ki = 4,300 nM), and the serotonin 5-HT2 receptor (Ki = 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] However, 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]

Chemistry

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Analogues

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Analogues of 5-HO-DPT include dipropyltryptamine (DPT), 4-HO-DPT (deprocin), 4-AcO-DPT (depracetin), 5-MeO-DPT, bufotenin (5-HO-DMT), 5-HO-DET, and 5-HO-DiPT, among others.

History

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

See also

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References

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