5-MeO-pip-T

Not to be confused with 5-MeO-PiPT.

5-MeO-pip-T, also known as 5-methoxy-pip-tryptamine, is a serotonin receptor modulator and selective serotonin 5-HT_1A receptor agonist of the tryptamine family related to 5-MeO-pyr-T.^[1][2]

5-MeO-pip-T

Clinical data
Other names	5-Methoxy-pip-tryptamine
Drug class	Serotonin receptor modulator; Selective serotonin 5-HT1A receptor agonist
ATC code	None
Identifiers
IUPAC name 5-methoxy-3-(2-piperidin-1-ylethyl)-1H-indole
PubChem CID	10467710
ChemSpider	8643121
ChEMBL	ChEMBL292921
Chemical and physical data
Formula	C16H22N2O
Molar mass	258.365 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)NC=C2CCN3CCCCC3
InChI InChI=1S/C16H22N2O/c1-19-14-5-6-16-15(11-14)13(12-17-16)7-10-18-8-3-2-4-9-18/h5-6,11-12,17H,2-4,7-10H2,1H3 Key:QVWFRPYLSDUCFB-UHFFFAOYSA-N

Use and effects

5-MeO-pip-T was described and partially synthesized by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), but he did not test it or define its properties or effects.^[1] According to Shulgin, he was not in a hurry to test it owing to the unfavorable effects of the structurally related 5-MeO-pyr-T.^[1]

Pharmacology

Pharmacodynamics

5-MeO-pip-T shows affinity for the serotonin 5-HT_2A receptor (K_i = 160–230 nM) but not for the serotonin 5-HT_2C receptor (K_i = >10,000 nM).^[2] It has been found to act as a low-potency and low-efficacy agonist of the serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 7,410 nM; E_maxTooltip maximal efficacy = 16%) and the serotonin 5-HT₄ receptor (EC₅₀ = 1,200 nM; E_maxTooltip maximal efficacy = 34%).^[3] These findings were also replicated in a subsequent study, where 5-MeO-pip-T showed far lower potency and efficacy as a serotonin 5-HT_2A receptor agonist than 5-MeO-DMT or 5-MeO-pyr-T.^[4] On the other hand, 5-MeO-pip-T was a potent full agonist of the serotonin 5-HT_1A receptor, with an EC₅₀ of 88.5 nM, although it was 42-fold less potent in this action than the highly potent 5-MeO-pyr-T.^[4] As such, 5-MeO-pip-T was described as a selective serotonin 5-HT_1A receptor agonist.^[4]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-pip-T has been described.^[2][3][1]

Analogues

Analogues of 5-MeO-pip-T include pip-tryptamine (pip-T), pyr-tryptamine (pyr-T), 5-MeO-pyr-T, 5-MeO-DMT, and 5-MeO-DET, among others.^[1]

5-MeO-mor-T

5-MeO-mor-T, the 5-methoxy derivative of mor-tryptamine (mor-T) and the analogue of 5-MeO-pip-T in which the piperidine ring is replaced by a morpholine ring, was also partially synthesized and briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), but he did not test it.^[1]

History

5-MeO-pip-T was first described in the scientific literature by Richard Glennon and colleagues by 1994.^[2] It was briefly described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).^[1] The pharmacology of 5-MeO-pip-T was described in greater detail in 2024.^[4]

See also

• Piperidinylethylindole
• Cyclized tryptamine