5-MeO-DPT

5-MeO-DPT, also known as 5-methoxy-N,N-dipropyltryptamine, as well as O-methyl-N,N-dipropylserotonin (O-Me-DiPS), is a psychedelic drug of the tryptamine family related to 5-MeO-DMT.^{[1][2][3][4][5]} It is taken orally.^[1] The drug has been encountered as a novel designer drug.^[6]

5-MeO-DPT

Clinical data
Other names	5-Methoxy-N,N-dipropyltryptamine; O-Methyl-N,N-dipropylserotonin; O-Me-DiPS
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT1A receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A US: Schedule I (isomer of 5-MeO-DIPT)
Pharmacokinetic data
Onset of action	12 minutes–<1 hour[1]
Duration of action	2–4 hours[1]
Identifiers
IUPAC name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine
CAS Number	69496-75-9 Y
PubChem CID	14011047
ChemSpider	14106484 Y
UNII	AYW60P516B
ChEMBL	ChEMBL169328 Y
CompTox Dashboard (EPA)	DTXSID70219723
Chemical and physical data
Formula	C17H26N2O
Molar mass	274.408 g·mol−1
3D model (JSmol)	Interactive image
Melting point	193 to 194 °C (379 to 381 °F)
SMILES CCCN(CCC)CCc2c[nH]c1ccc(cc12)OC
InChI InChI=1S/C17H26N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h6-7,12-13,18H,4-5,8-11H2,1-3H3 Y Key:PNHPVNBKLQWBKH-UHFFFAOYSA-N Y
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Use and effects

Alexander Shulgin included 5-MeO-DPT in a subsection in the 5-MeO-DET entry of his book TiHKAL (Tryptamines I Have Known and Loved).^[1] He did not explicitly provide a dose range or duration for 5-MeO-DPT, but did report having tried it at doses of 4 to 8.4 mg orally, with 4 mg producing only threshold effects and doses of 6 to 8.4 mg being more meaningfully active.^[1] In a subsequent literature review however, Shulgin gave an explicitly defined dose range of 6 to 10 mg orally.^[7] Its onset was described as being 12 minutes to within 1 hour and its duration was 2 to 4 hours.^[1]

According to Shulgin, 5-MeO-DPT's actions are ambiguous and not totally positive.^[1] This led to him tucking discussion of the drug away in the 5-MeO-DET entry of TiHKAL as opposed to giving 5-MeO-DPT its own entry in the book.^[1] The effects of 5-MeO-DPT were only vaguely described.^[1] The 4 mg dose produced only threshold effects described as "something".^[1] At the 6 mg dose, the effects included possible eroticism, not too much lightheadedness, and comfortableness, with a plus-two rating on the Shulgin Rating Scale.^[1][8] On the other hand, at the 8.4 mg dose, there were 5-MeO-DMT-like "head noises" or "bells" described as "bad" and an underlying 5-MeO-DMT-like "turn on" described as "good".^[1][8] However, per Shulgin, while these effects alternated, the unpleasant negative effects overall outweighed the positive and desired effects.^[1][8] There were no apparent cardiovascular effects at this dose.^[1] Shulgin stated that he had "better things to do with my time" and did not further explore 5-MeO-DPT or evaluate higher doses.^[1]

5-MeO-DPT's lower homologue 5-MeO-DET was found to produce unique and strong side effects such as lightheadedness, dizziness, and vertigo at low doses which precluded it from being tolerated or used at hallucinogenic doses.^[1] Shulgin synthesized and tested 5-MeO-DPT in the hopes that the vertigo-related side effects of 5-MeO-DET would be reduced or eliminated while the hallucinogenic and other desired effects such as sexual enhancement would be preserved.^[1] However, while 5-MeO-DET-like side effects were not described, Shulgin nonetheless deemed 5-MeO-DPT an unpromising compound.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

5-MeO-DPT activities

Target	Affinity (Ki, nM)
5-HT1A	4–149 (Ki) 5–476 (EC50Tooltip half-maximal effective concentration) 43–95% (EmaxTooltip maximal efficacy)
5-HT1B	1,800–>10,000
5-HT2A	7–655 (Ki) 6–684a (EC50) 81a–101% (Emax)
5-HT2B	33
5-HT2C	1,086–1,290 (Ki) 810a (EC50) 96%a (Emax)
5-HT3	>10,000
5-HT5A	>10,000
5-HT6	427
5-HT7	84
KOR	1,211
SERTTooltip Serotonin transporter	1,031–1,070 (Ki) 910 (IC50)
NETTooltip Norepinephrine transporter	>10,000 (IC50)
DATTooltip Dopamine transporter	16,998 (IC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1Tooltip inositol phosphate formation. Sources: [8][9][10] [11]

5-MeO-DPT is a potent and high-efficacy agonist of the serotonin 5-HT_2A and 5-HT_1A receptors.^{[8][9][10][12]} Additionally, the drug has been found to act as a weak serotonin reuptake inhibitor and serotonin 5-HT_2C receptor agonist with lower potency.^[8][10]

The drug fully substitutes for the serotonin 5-HT₂ receptor agonist and serotonergic psychedelic DOM in rodent drug discrimination tests and partially substitutes for the serotonin 5-HT_1A receptor agonist 8-OH-DPAT in these tests followed by behavioral disruption at higher doses.^[9] 5-MeO-DPT also substitutes for 5-MeO-DMT in rodent drug discrimination tests.^[13]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-DPT has been described.^[1]

Analogues

Analogues of 5-MeO-DPT include dipropyltryptamine (DPT), 4-HO-DPT (deprocin), 4-AcO-DPT (depracetin), 5-HO-DPT, 5-MeO-DMT, 5-MeO-DET, 5-MeO-DALT, 5-MeO-DBT, 5-MeO-DiPT, 5-MeO-MPT, and 5-MeO-EPT, among others.^[1]

History

5-MeO-DPT was first described in the scientific literature by Richard Glennon and colleagues by 1979.^[14][15] It was described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).^[1] The drug was encountered as a novel designer drug in Europe in 2010.^[6]

Society and culture

Legal status

United States

In the United States, 5-MeO-DPT is considered a Schedule I controlled substance as a positional isomer of 5-MeO-DiPT.^[16]

See also

• Substituted tryptamine