Last updated
IUPAC name
Other names
  • 5-Methoxy-N,N-tetramethylenetryptamine
  • Indole, 5-methoxy-3-[2-(1-Pyrrolidyl)-Ethyl]
  • 1-[2-(5-Methoxy-1H-indol-3-yl)ethyl]pyrrolidine
  • "Pyrrolidyl-5-methoxy-tryptamine"
3D model (JSmol)
PubChem CID
  • InChI=1S/C15H20N2O/c1-18-13-4-5-15-14(10-13)12(11-16-15)6-9-17-7-2-3-8-17/h4-5,10-11,16H,2-3,6-9H2,1H3 Yes check.svgY
  • InChI=1/C15H20N2O/c1-18-13-4-5-15-14(10-13)12(11-16-15)6-9-17-7-2-3-8-17/h4-5,10-11,16H,2-3,6-9H2,1H3
  • O(c3ccc1c(c(c[nH]1)CCN2CCCC2)c3)C
Molar mass 244.338 g·mol−1
AppearanceOff-white oil
Density 200.3g/cm3
Melting point 164 to 167 °C (327 to 333 °F; 437 to 440 K) Melting point given for hydrochloride salt.
Boiling point 160 to 170 °C (320 to 338 °F; 433 to 443 K) Boiling point for freebase at 0.05mm/Hg.
log P 2.75270
Vapor pressure 7.42x10−07mm/Hg
Oral, Vaporized
Unknown, likely under several hours.
Several hours.
Legal status
Flash point 200.3 °C (392.5 °F; 473.4 K)
Lethal dose or concentration (LD, LC):
6250 μg/kg (Rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, [1] who credited S. Mitzal for characterization of chemical properties. [2] Later human tests were reported by Alexander Shulgin, in his book TiHKAL . An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening. [3]



Testing was performed on rats using this compound while characterizing various agonists of the 5-HT7 receptor. It is an agonist with a Ki value of 630.96nM. [4]

Very little other data exists about the pharmacological properties, metabolism, and toxicity of 5-MeO-pyr-T.

See also

Related Research Articles

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5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

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4C-B is a lesser-known psychedelic drug which is related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy. It is briefly mentioned in Alexander Shulgin's book PiHKAL but was never tested by him, however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.

<i>O</i>-Acetylbufotenine Chemical compound

O-Acetylbufotenine is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors.


  1. Hunt, R. R.; Brimblecombe, R. W. (July 1967). "Synthesis and Biological Activity of Some Ring-Substituted Tryptamines". Journal of Medicinal Chemistry. 10 (4): 646–648. doi:10.1021/jm00316a027. PMID   4962512.
  2. Mitzal, S. (1962). "N/A". Dissertationes Pharm. 14: 305.
  3. Shulgin, Alexander; Shulgin, Ann (1997). TiHKAL, The Continuation (1st ed.). Berkeley, CA, USA: Transform Press. pp. 548–551. ISBN   0-9630096-9-9 . Retrieved 7 April 2018.
  4. Vermeulen ES, Schmidt AW, Sprouse JS, Wikström HV, Grol CJ. Characterization of the 5-HT(7) receptor. Determination of the pharmacophore for 5-HT(7) receptor agonism and CoMFA-based modeling of the agonist binding site. J Med Chem. 2003 Dec 4;46(25):5365-74. doi : 10.1021/jm030826m PMID   14640545