Pip-Tryptamine

pip-Tryptamine (pip-T), also known as N,N-pentamethylenetryptamine, N,N-piperidyltryptamine, or 3-(2-piperidinoethyl)indole, is a serotonin receptor modulator and possible serotonergic psychedelic of the tryptamine family.^{[1][2][3][4][5][6]} It is the derivative of tryptamine in which the amine has been cyclized into a piperidine ring.^[1][2][3]

pip-Tryptamine

Clinical data
Other names	3-(2-Piperidinoethyl)indole; N-Piperidyltryptamine; N,N-Piperidyltryptamine; Piperidinyltryptamine; Piperidinotryptamine; PIT; N,N-Pentamethylenetryptamine
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 3-(2-piperidin-1-ylethyl)-1H-indole
CAS Number	26628-87-5
PubChem CID	33560
ChemSpider	30961
ChEMBL	ChEMBL2138465
CompTox Dashboard (EPA)	DTXSID70181173
Chemical and physical data
Formula	C15H20N2
Molar mass	228.339 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CCN(CC1)CCC2=CNC3=CC=CC=C32
InChI InChI=1S/C15H20N2/c1-4-9-17(10-5-1)11-8-13-12-16-15-7-3-2-6-14(13)15/h2-3,6-7,12,16H,1,4-5,8-11H2 Key:PJVCNRSWJSLGCV-UHFFFAOYSA-N

Use and effects

pip-T was only briefly mentioned by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved).^[2] Its properties and effects were not described.^[2]

Interactions

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

Pharmacology

Pharmacodynamics

The affinities (IC₅₀Tooltip half-maximal inhibitory concentration) of pip-tryptamine for serotonin receptors were 600 nM for the serotonin 5-HT_1A receptor, 760 nM for the serotonin 5-HT_2A receptor, and 1,250 nM for the serotonin 5-HT_2B receptor, whereas other serotonin receptors were not reported.^[1][3] The affinity of pip-T for the serotonin 5-HT_2A receptor was about 10-fold lower than that of dimethyltryptamine (DMT) and was about 7-fold lower than that of pyr-tryptamine (pyr-T; N,N-pyrrolidinyltryptamine).^[3]

The drug produces hypolocomotion in rodents.^[4] In addition, it induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[4] This was blocked by the serotonin 5-HT_2A receptor antagonist ketanserin.^[4] Hence, the drug may have hallucinogenic effects in humans.^[4] Conversely, pip-T did not produce conditioned place preference (CPP) and was not self-administered, suggesting that it lacks reinforcing properties and misuse potential, similarly to most other tryptamines.^[4]

Chemistry

Synthesis

The chemical synthesis of pip-T has been described.^[2]

Analogues

Analogues of pip-T include 5-MeO-pip-T, 10,11-secoergoline (α,N-Pip-T), pyr-T, MPMI, SN-22, RU-24,969, and EMD-386088, among others.

mor-Tryptamine

mor-Tryptamine, or mor-T, also known as 3-(2-morpholinoethyl)indole, is the analogue of pip-T with the piperidine ring replaced with a morpholine ring.^[2] It was briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), including its chemical synthesis.^[2] The drug was tested by intramuscular injection of 30 mg as the fumarate salt, but produced no effects whatsoever.^[2] The 5-methoxy derivative of mor-T, 5-MeO-mor-T, is also known, but is not known to have been tested.^[2]

History

Pip-T was first described in the scientific literature by 1959^[5] and was more thoroughly characterized in 1990^[1][3] and 2020.^[4]

See also

• Substituted tryptamine
• Cyclized tryptamine